The Fall and Rise of the Pittsburgh Pirates: 100 Moments From The Streak

PNC Park Blackout

This article was originally published on Pirates Prospects on September 9, 2013. It’s part of our Greatest Hits archives from over a decade of posts on the original site.

With the Pirates winning game 82 tonight, I wanted to do something to recap the 20 years of losing. I thought about doing a chart recapping the high and low points since 1992 with a line graph. That led to me gathering any key moments during the losing streak. I looked through every single season and looked at every key moment during the streak. Some of the moments led to the current winning team. Some of the older moments were big reasons why the Pirates lost for so long. Some moments were insignificant in the long-term, and sometimes even in the short-term, but became legend during the streak.

I documented them all, and originally was going to go with a straight list of events. Then the Pirates lost last Wednesday, so I decided to expand with a few thoughts. They kept losing, and I kept expanding my thoughts, leading to a much longer article than I anticipated. But the result is that I feel I’ve captured almost every key moment, big and small, during the losing streak. There might have been a few things I missed. I know there were a few things I cut or combined into group events, just to get the list to a round 100 number. The end result is almost 8000 words, and a detailed timeline of The Streak from the end of the 1992 season to win number 82 tonight. I hope you enjoy. Or, since I know how I felt when I was gathering all of these moments, I hope the 1992-2012 years don’t get you too down, or allow you to really appreciate what is happening this year. My suggestion: after every 20 moments on the list, take a break and look at the current standings page. Trust me, it helps. Another thing that helps: whiskey.


1. Sid Bream (10/14/1992) – I don’t think anything else needs to be said. There will be a lot of video in this post, but not for this moment.

2. Barry Bonds and Doug Drabek granted free agency (10/26/1992) – It would be a long time before the Pirates got a pitcher as good as Drabek or a hitter as good as Bonds.

3. (1993) The Pirates lose 87 games in year one of the losing streak.

4. (1994) The Pirates go 53-61 in the strike shortened season for year two.

5. Andy Van Slyke granted free agency (10/21/1994) – Van Slyke was no longer the player he was during his prime. I remember seeing him the following season in Baltimore, and he wasn’t the same as he was in Pittsburgh. That was his last season. His departure was more of a sign that the Pirates lost another key player from their ’90-92 stretch than the loss of someone who was a key player then.

6. The Pirates release Tim Wakefield (4/20/1995) – A week later he signed with the Boston Red Sox and went on to put up a 2.95 ERA in 27 starts with Boston that year. The Pirates would have many moments where they gave up on a player too soon, but this might have been the biggest. Wakefield was good immediately, and went on to pitch in the majors for 17 more years.

7. Chad Hermansen drafted (6/1/1995) – I was trying to find a way to fit Hermansen in here. There wasn’t really any big moment. He’ll show up later in the list, but that was more about the other player involved. Hermansen was a “can’t miss” prospect who…missed. A lot of Pirates prospects did that for a long period, but Hermansen became the poster child, to the point where every prospect you talked about was met with a “He’s just the next Chad Hermansen.” That actually lasted until Andrew McCutchen didn’t become the next Chad Hermansen.

8. (1995) The Pirates lose 86 games. Year three.

9. Kevin McClatchy leads a group to buy the Pirates for $90 million (February 1996).

10. (1996) The Pirates lose 89 games, the most in their four-year losing streak. But there would be many more…

11. Pirates trade Denny Neagle, Carlos Garcia, Orlando Merced, Jay Bell and Jeff King (August-December 1996) – This is when things really came apart. The Pirates blew up the roster, going for the complete rebuild. Part of this was due to finances, the ownership change and pulling for a new stadium.

12. Francisco Cordova and Ricardo Rincon combine for a 10-inning no-hitter (7/12/1997) – This was probably one of the best moments from the losing streak. I also think this pretty much sums up the 1997 Freak Show. Less than a week later, they moved into first place on July 17.

13. Shawon Dunston hits two homers in his Pirates debut (9/2/1997) – The Pirates weren’t expected to do anything in 1997. Dunston’s home runs led them to a win, a 69-70 record, and put them 1.5 games back in the division. That was the closest they would get to .500 and first place the rest of the year.

14. (1997) The Freak Show loses 83 games. Year five.

15. Joe Randa selected by Arizona in the expansion draft (11/18/1997) – This was probably one of the most under-rated bad moves by the Pirates. They left Randa unprotected, which led to them calling Aramis Ramirez up too early. That led to Ramirez struggling, becoming arbitration-eligible before he was established and getting traded before he even broke out as a top player in the majors.

16. Turner Ward and Jose Guillen in the outfield (5/3/1998) – These don’t really have any significance to the streak, but they were both memorable plays. First was Turner Ward running through a wall on May 3rd:

The next play was Jose Guillen with one of the most amazing throws from the outfield, just two months later:

17. (1998) Pirates lose 93 games, capped off by a 5-22 run in September, which was their worst month during the streak. Year six.

18. Brian Giles acquired for Ricardo Rincon (11/18/1998) – This was easily one of the best trades ever made during the losing streak, and maybe one of the best in Pirates history. It’s also what fueled my “always trade relievers” mentality to this day. Giles went on to hit 35+ homers in each of the next four seasons, before being traded in 2003 in another huge deal.

19. Jon Lieber traded to the Cubs (12/14/1998) – A month after the Giles trade, only this one didn’t go as well. The Pirates got Brant Brown, and Lieber went on to pitch for nine more years.

20. Jason Kendall breaks his ankle (7/4/1999) – The Pirates were 40-39 heading into that game, and lost. They also went downhill, losing 83 games. You’d have to think that with Kendall in the lineup for the second half they might have ended the losing streak.

21. Jose Guillen traded to the Rays (7/23/1999) – Guillen was traded in year three of his 14-year career. He was probably brought up too early, jumping straight from high-A to the majors in 1997. Could he have broken out with the Pirates and played with them for most of the early 2000’s with proper development?

22. (1999) Pirates lose 83 games. Seven years.

23. The 2000 draft (6/5/2000) – This was one of the best pre-Huntington drafts the Pirates had during the streak. They got Sean Burnett in the first round, but landed a lot of big players in the middle rounds, thanks to Mickey White. Those players included Chris Young, Jose Bautista, Ian Snell and Nate McLouth.

24. Jack Wilson acquired for Jason Christiansen (7/29/2000) – Wilson would go on to be the best shortstop during the streak, and a fan favorite.

25. (2000) Pirates lose 93 games. Eight years.

26. Bad contract extensions (1999-2000) – In preparation for the opening of PNC Park, the Pirates made a lot of bad contract decisions. Kevin Young and Pat Meares signed extensions in early 1999. Jason Kendall was signed to a horrible deal after the 2000 season. All of those paved the way for one of the worst moves in franchise history a few years later.

27. PNC Park opens/Willie Stargell passes away (4/9/2001) – The Pirates opened one of the best parks in baseball, but sadly one of their best players of all time passed away on the same day.

28. John VanBenschoten drafted as a pitcher (6/5/2001) – Every other team was looking at JVB for his bat, but the Pirates took him as a pitcher. He had several arm injuries and eventually didn’t even have the option to become a hitter because of all of his arm surgeries. The impact of this move is still seen today. When the Pirates made Stetson Allie a pitcher, and he struggled, there were JVB comparisons.

29. Lloyd McClendon steals first base (6/26/2001) – This pretty much sums up Lloyd McClendon’s managerial career.

30. Dave Littlefield hired (7/13/2001) – We have 70 to go in this countdown, but they’re going to start flying by after this move.

31. Brian Giles hit a walk off grand slam against Billy Wagner (7/28/2001) – One of the most memorable games in PNC Park. Watch it below.

Two years later he would make this amazing play, which was the runner up in “which Brian Giles moment should I feature”. But it’s the internet, so I can show video for both:

32. Jason Schmidt and John Vander Wal traded for Ryan Vogelsong and Armando Rios (7/30/2001) – This move summed up every pitching move ever during the streak. Schmidt had a lot of upside, but never realized that with the Pirates. Almost immediately he was a top-of-the-rotation pitcher with San Francisco. Vogelsong was a top prospect who was derailed by injuries. Ten years after this move, Vogelsong returned (with the Giants) and had an amazing comeback after five years away from the majors, posting a 2.71 ERA in 179.2 innings. To recap, we have an ace who never realized his potential with the Pirates, a top prospect who busted with the Pirates, and then somehow got everything to click with another team.

33. (2001) The Pirates lose 100 games, the most in their nine year losing streak.

34. Pirates replace Mickey White with Ed Creech (11/21/2001) – This was one of the worst moves the Pirates made under Littlefield, possibly worse than the Aramis Ramirez trade. White oversaw some of the best drafts during the streak, while Creech oversaw drafts like…well, we’ll get to those.

35. Todd Ritchie traded for Kip Wells, Josh Fogg, and Sean Lowe (12/13/2001) – This wasn’t a bad trade at all. Wells and Fogg provided more combined value than Ritchie would have. Before I focused much on Mickey White, and before I got a chance to see Dave Littlefield’s track record, this move encouraged me.

36. Operation Shutdown (3/29/2002) – Right before the 2002 season began, Derek Bell left the team, citing “Operation Shutdown.” This was because he didn’t feel like he needed to compete for a job in Spring Training. Bell was in the second year of a two-year deal, but struggled in the first year. He never played in the majors again.

37. Aramis Ramirez hurts his ankle in a brawl (4/17/2002) – The Pirates won this game, going 9-5 on the year. They went on to win three more games in a row after this. But I always felt the Ramirez injury pretty much turned the tide that season. Not that there’s any sort of tide after half a month. But Ramirez had a .904 OPS at the time of the injury, and went downhill because he wasn’t given the proper time to rehab the injury.

38. Pirates draft Bryan Bullington (6/4/2002) – With the first overall pick the Pirates took Bryan Bullington…then said he has the upside of a number three starter. Meanwhile, they passed on B.J. Upton, the top player in the draft. This was the first draft under Ed Creech.

39. Darren Lewis retires after being traded to the Pirates (8/2/2002) – This wasn’t the best period for the Pirates to attract players. There was Operation Shutdown. Later in the year the Pirates traded Chad Hermansen to the Cubs for Darren Lewis. Rather than joining the Pirates, Lewis retired.

40. (2002) The Pirates lose 89 games. Year ten.

41. Pirates sign Reggie Sanders, Kenny Lofton, Jeff Suppan and Matt Stairs (March 2003) – MLB owners were stuck colluding against free agents, which allowed the Pirates to have one of their best off-seasons yet. All of these guys had great numbers that year, but the Pirates wouldn’t have free agent success like this for a while.

42. Randall Simon hits a sausage with a baseball bat (7/9/2003) – This is another weird moment during the streak. We joke now, but this was a big deal at the time, as shown by this way-too-serious news clip.

43. The Aramis Ramirez trade (7/23/2003) – This was one of the worst moves of all time, although it wasn’t fully the fault of Littlefield. The Pirates had to get under the debt-equity ratio by dumping salary (MLB later made it so teams didn’t have to make a trade like this to get under the ratio). Kris Benson was injured a few weeks earlier, making Ramirez the only guy they could trade. That gave them no leverage, and the result was that they got Jose Hernandez (33 years old at the time), Matt Bruback (a 24-year-old Triple-A pitcher) and a PTBNL. It was said that the deal would look better when the PTBNL was announced, thus spawning every “wait for the PTBNL” joke in future years. Bobby Hill was that PTBNL and it didn’t make the deal better. Also, to make room for Hill on the 40-man roster, the Pirates waived Bruback and lost him on waivers. So the deal was pretty much Bobby Hill and 33-year-old strikeout king Jose Hernandez for Ramirez and Kenny Lofton, who was thrown in because you’re not getting Bobby Hill for just Ramirez.

There are so many weird things about this deal, but the Bruback part is the weirdest for me. It represents everything that was wrong with Littlefield. Bruback didn’t do anything in his career, remaining in the minors until he retired at 27. But the questions raised are: 1. Why trade for him if you’re going to get rid of him shortly? 2. Why not get rid of the 33-year-old instead of the 24-year-old when you’re clearly rebuilding? 3. This is a situation where the Pirates went for immediate major league help, rather than going deeper in a farm system to get a prospect who could be a much better player down the line.

44. Pirates acquire Freddy Sanchez in a deal with Boston (7/31/2003) – This deal was one of Littlefield’s best trades, in spite of Littlefield. This was actually a deal to correct an earlier move. The Pirates sent Mike Gonzalez and Scott Sauerbeck to Boston for Brandon Lyon and Anastacio Martinez. It was later found that Lyon was injured, and Boston knew about it. So to make up for that, they reversed the deal. The Pirates got Gonzalez back, the Red Sox got Lyon and Martinez back, and they included a Jeff Suppan for Freddy Sanchez swap. If Lyon is healthy, Littlefield doesn’t get Sanchez, and trades away Mike Gonzalez.

45. Brian Giles traded for Jason Bay and Oliver Perez. (8/26/2003) – This was Littlefield’s best move, but again it was in spite of him. He wanted Xavier Nady, and settled for Bay, who ended up being the best player he acquired. A few years later he would get Nady by trading Perez to the Mets.

46. (2003) The Pirates lose 87 games for year 11. They actually improved from their 100-loss campaign, winning 70+ two years in a row. But they clearly weren’t improving, and the winning this year was largely from guys who wouldn’t be with the team the following year.

47. The 2003 Rule 5 Draft and other horrible roster management (2003) – The Bullington draft pick was the first sign that Littlefield didn’t know what he was doing. 2003 confirmed it. The most infamous move was when the Pirates lost five of the first six players in the 2003 Rule 5 draft, and then didn’t even make a pick with their open spot. Some of the players they lost eventually returned. Chris Shelton went on to have a monster April 2004, drawing comparisons to Albert Pujols before cooling down. Jose Bautista floated from team to team before the Pirates traded for him again. Jeff Bennett was lost, pitching the whole year in Milwaukee’s bullpen. He wasn’t a big loss, as he only went on to pitch three more years in relief.

It wasn’t just the Rule 5 draft. Prior to the 2003 season the Pirates lost Bronson Arroyo on waivers to the Red Sox. They also released Matt Herges, after trading Chris Young to get him three months earlier in the off-season. Herges was released at the end of Spring Training, and we know what happened with Young. In the 2003 off-season the Pirates waived Matt Guerrier, who has had a long and successful career as a reliever. So why all of these moves? Who was holding up roster spots?

Chris Stynes, Daryle Ward, Randall Simon, and Raul Mondesi. Rather than protecting young players in a clear rebuilding period, Littlefield went for one-year rentals, in what Wilbur Miller titled “The Drive for 75”.

48. Raul Mondesi leaves the team (5/11/2004) – Mondesi left the team and was released ten days later. Nine days after being released he returned and signed with the Angels. File this with Derek Bell and Darren Lewis.

49. Rob Mackowiak Double Header (5/28/2004) – These were two of the best games during a very dark time in the Pirates losing stretch. In game one, Mackowiak hit a walk-off grand slam in the bottom of the ninth inning. In game two he hit a two-run homer in the bottom of the ninth inning, sending the game to extra innings where Craig Wilson would win it with a solo homer. All of this happened on the day that Rob’s son, Garrett Mackowiak, was born.

50. Pirates draft Neil Walker (6/7/2004) – Walker is from the Pittsburgh area, so you can’t really speak bad about this pick. But truthfully this was another sign that Littlefield wasn’t the guy for the job. Sure, the pick worked out after some delay, but Littlefield passed on Jered Weaver, the top prospect in the draft. This was the second time Littlefield passed on a hard-to-sign guy to take a signable guy with less upside. The biggest was yet to come.

51. Kris Benson traded to the Mets (7/30/2004) – The Pirates got Ty Wigginton, Matt Peterson, and Jose Bautista in this deal, while sending away Jeff Keppinger to make sure they got Bautista back. There were a lot of things wrong about this move. First, there was an effort to get Bautista back, which wouldn’t have been necessary if they would have protected him over the off-season. Second, the Mets traded Scott Kazmir for Victor Zambrano, who was a lesser pitcher than Benson. Third, the Pirates turned down Ryan Howard for Benson, because they already had Brad Eldred in Double-A.

52. (2004) The Pirates lose 89 games to make it 12 years in a row. There were some positives here. Jason Bay was named the rookie of the year. Oliver Perez struck out 239 batters, giving some hope for the future.

53. Jason Kendall salary dumped (11/27/2004) – Kendall’s career was derailed by a thumb injury, and his contract was a huge albatross for the Pirates. They finally got rid of him, dealing him to Oakland. The problem with having more money available to spend is that it does no good if the GM you have can’t spend it properly.

54. Tike Redman batting third (4/4/2005) – It only happened once, but this was one of the defining moments of Lloyd McClendon’s time as a manager. It was based on computer simulations, which was a concept that was mocked at the time. Or maybe it was just that any computer saying Redman was the best #3 hitter was probably still running Windows 95.

55. Andrew McCutchen drafted (6/7/2005) – This was the best draft pick Littlefield made. The problem? He didn’t really make it. I’ve been told by people in the organization at the time that the scouts begged Littlefield to take McCutchen. This kind of makes you wonder whether Ed Creech was actually that bad, or if it was Littlefield getting involved. Creech didn’t really do much in the middle or late rounds, so this doesn’t totally absolve him.

56. Oliver Perez kicks a laundry cart (6/28/2005) – Perez had a strange Pirates career. He struck out 239 in his first full season. The following year was typical for the Pirates post-Doug Drabek. They think they have an ace, then he fails to repeat his big year. Perez starred in one of the best Pirates commercials ever in 2005, but was inconsistent, leading to him kicking a laundry cart out of frustration and breaking his toe. The following year he was traded to New York for Xavier Nady. On a side note, I will do horrible, disgusting, unforgivable things if someone can find and upload the Oliver Perez “Lots of heat” commercial. How is this not on the internet?

57. Jason Bay goes 0-for-the home run derby (7/12/2005) – On the flip side, Jason Bay was actually repeating his big breakout year, and was placed in the home run derby. This was a chance for Pirates fans to finally see a young guy get national attention, which was always so important during the losing streak. Instead, Bay hit zero homers and became the joke of the event.

58. (2005) Pirates lose 95 games for year 13.

59. Blocking young players with veterans (2005-2006) – A big trend during Littlefield’s time was that he blocked prospects and young players with veterans. In 2005 he traded Leo Nunez (sorry, Juan Carlos Oviedo) for Benito Santiago. This was despite the fact that the Pirates had Ryan Doumit and Ronny Paulino waiting in the wings. Santiago played six games with the Pirates in 2005. In 2006 he signed Joe Randa to play third base over Freddy Sanchez, even though Sanchez put up strong numbers the year before. That move looked worse when Sanchez won the batting title in 2006, only after stealing the job from Randa. Jeromy Burnitz was also signed, blocking Nate McLouth in right field.

60. Chris Duffy leaves the team because of Jim Tracy (5/18/2006) – I always thought McClendon was a bad manager, but he wasn’t nearly as bad as Jim Tracy. The way Tracy approached things was that all success was his doing and all failures were the fault of the player. He ended up driving Chris Duffy insane, and Duffy left the team after being optioned to Triple-A. Duffy had issues with Tracy trying to change his batting style, which was strange, because Duffy hit for a .341 average and an .814 OPS in 126 at-bats the previous year. He eventually returned, but never had success again in the majors.

61. 13-game losing streak (6/15/2006) – The Pirates lost 13 in a row, ending on June 15th, which marked their longest losing streak of games during the losing streak.

62. The All-Star Game in Pittsburgh (7/11/2006) – Pittsburgh actually hosted two All-Star games during the streak, but this one was notable because it was the most important thing that ever happened at PNC Park.

63. The 2006 Trade Deadline (7/31/2006) – Here were the moves the Pirates made: Sean Casey for Brian Rogers (23-year-old AA reliever). Roberto Hernandez/Oliver Perez for Xavier Nady. Craig Wilson for Shawn Chacon. Kip Wells for Jesse Chavez. The moves weren’t bad, but they just represented treading water. Littlefield never actually blew the team up. He traded a lot of guys in 2003, but spent the next three years blocking young players with one year veteran signings. Then his trades sent out guys who weren’t winning in Pittsburgh, for similar guys who wouldn’t win in Pittsburgh. Nady was a good move, but Chacon and Chavez were never leading to winners in Pittsburgh, and the Pirates weren’t close enough to be trading for anything other than prospects.

64. (2006) Pirates lose 95 games for year 14.

65. Starling Marte signed (1/4/2007) – This was pretty much the only big international signing to come from Littlefield, although it wasn’t a big signing. Marte received $85,000, struggled in 2007, and his development as a prospect came under Neal Huntington. The international levels were bad under Littlefield. He had no focus on international players, despite the fact that Roberto Clemente’s name gave the Pirates the inside track with a lot of players in Latin America. The biggest move he made was signing Yoslan Herrera to a big deal out of Cuba, which was more for show than anything else. Ultimately, the lack of focus on the international markets was a big reason for Littlefield’s downfall. As for Marte, he ended up playing a big role in the turnaround.

66. Pirates acquire “Lefty McThump” (1/19/2007) – All throughout the 2006/07 off-season, Littlefield talked about how the Pirates needed to find “Lefty McThump” — a power hitter to put in the middle of their lineup. That player ended up being Adam LaRoche, and the deal wasn’t a bad one. The Pirates sent Mike Gonzalez and Brent Lillibridge to Atlanta for LaRoche and Jamie Romak. The only problem with the deal was that LaRoche was more of a support player than a guy who could carry an offense. He had a good career in Pittsburgh, but was advertised as the guy who would carry the offense, which set fan expectations way too high.

67. Daniel Moskos drafted instead of Matt Wieters (6/7/2007) – I’ve pointed out how Littlefield passed over hard-to-sign players for guys who were signable with lower upsides. Bryan Bullington over B.J. Upton. Neil Walker over Jered Weaver. If you want another story, how about Brad Lincoln. The Pirates took Lincoln fourth overall that year. A lot of more successful pitchers went after Lincoln. Two years ago I was told a story from a scout with the Pirates at the time. I mentioned how the scouts begged Littlefield to take McCutchen in 2005. They didn’t win in 2006. The scouts loved a left-handed prep pitcher that year. They loved him so much that Littlefield went to see him pitch. It was a cold game, and the lefty had a bad outing. Based on that one start, Littlefield crossed the guy off the list, even though his scouts were high on this player. Who was that pitcher? Clayton Kershaw.

It wasn’t until the 2007 draft that Littlefield’s bad drafting caught up with him. He took Daniel Moskos over Matt Wieters. Wieters was the top position player in the draft, and fell to the Pirates at number four. Moskos was a top ten prospect, but profiled as a lefty reliever who could make the majors quickly. Once again, Littlefield passed over upside for a small, quick fix at the majors. Only this time, fans went crazy.

68. The Matt Morris trade (7/31/2007) – What made the Moskos pick more infuriating was that Littlefield traded for Matt Morris at the deadline. Morris had a lot of money still owed to him, and the Pirates took it all on, while also trading away Rajai Davis. The Pirates were nowhere near a contending team, so the additions of Morris and Moskos with the goal of immediate help came across as a job saving move. If you want to find a rock bottom to the streak, this series of events was that rock bottom.

69. Dave Littlefield fired / Neal Huntington hired (September 2007) – This is when things turned around. I don’t want to say that Huntington was some savior. It was rough the first two years under Huntington, and anyone would have improved over Littlefield (who I’ve bashed a lot here, but he’s a really nice guy who was just very bad at his job). But this was the point where things turned around.

70. (2007) 94 losses extends the streak to 15 years. Again, why did they trade for Matt Morris?

71. The 2008 draft (6/5/2008) – This was one of the best drafts the Pirates had in a long time, although it took several years to turn out that way. They took Pedro Alvarez in the first round, which was very refreshing after the Moskos incident and all of the other issues in previous years. They also got Jordy Mercer and Justin Wilson, who have helped this year. Robbie Grossman was the key prospect in the Wandy Rodriguez trade, and was an over-slot pick in this draft. Over-slot was something the Pirates never did before. Other guys who have appeared with the Pirates from the 2008 draft include Chase d’Arnaud and Matt Hague. But just getting Alvarez, Mercer, and Wilson, plus the trade chip in Grossman, makes this a great draft year after so many bad years. Also, after the draft signing deadline in August, Bob Nutting said he felt like he had “the single best management team in all of baseball, maybe in all of sports”. That was shortened to TBMTIB in comments and on message boards, and became a Pirates meme for years.

72. The Bay and Nady Trades (Late July 2008) – At the time the Jason Bay trade was seen as a good move, and the Nady trade was criticized. It turned out that those deals were reversed. The Bay traded ended up horrible, with Andy LaRoche busting, Brandon Moss struggling in his time with the Pirates only to find success with Oakland, and Craig Hansen getting injured and never being the same. Bryan Morris is the only thing left, and he’s a reliever. The Nady trade was a great move. The Pirates didn’t get a lot of long-term value to this day, but they got great seasons from Ross Ohlendorf and Jeff Karstens in the rotation, plus Daniel McCutchen in the bullpen. Jose Tabata is the key long-term piece from that move, although he looks to be an expensive fourth outfielder due to his extension.

The worst part about the Bay trade might have been the non-trade the previous off-season. The Pirates had a reported deal to send Bay and Ronny Paulino for Cliff Lee, Franklin Guttierez, and Kelly Shoppach. President Frank Coonelly reportedly didn’t like the deal, and it was eventually killed. At the time Cliff Lee was the main piece, and was coming off a horrible season. But he broke out in 2008, and the trade would have been huge for the Pirates, except for the part when they eventually would have tried to trade Lee, only to realize that no one gets anything of value in a trade for Cliff Lee. Actually, this might have been why the deal was killed.

73. The Jose Bautista trade (8/21/2008) – The Pirates traded Bautista on waivers to Toronto in exchange for Robinzon Diaz. Bautista didn’t have a lot of value, as he was a utility player who was set to get a raise through arbitration. After a year and a half with Toronto, he was almost non-tendered. Then he broke out in 2010 to become the biggest power hitter in the game. You can’t fault the Pirates for selling low on Bautista, since it was impossible to see what would come next. However, you can fault them for trading him away due to salary, and then signing Ramon Vazquez to a two year deal that off-season. They were rebuilding, and Bautista had some upside, while the 32 year old Vazquez had none. This was a move that was Littlefield-esque. Maybe Bautista doesn’t break out with Pittsburgh, but the reason for trading him made no sense when paired with the addition of Vazquez to the bench.

74. Pedro Alvarez deal hits a snag (8/27/2008) – It wasn’t going to be easy for the Pirates. In 2007, major league baseball moved the draft signing deadline up to August, and added a midnight deadline. This led to a few rumored signings after the deadline. 2008 was the second year of this system. Pedro Alvarez agreed for $6 M, and it was later revealed that Buster Posey got more, even though he was picked a few spots after Alvarez. Scott Boras used the post-deadline deal to try and void the agreement with Alvarez. The Pirates placed Alvarez on the restricted list on August 27th after he didn’t show up and sign the deal. It was clearly Boras angling for more money, since Eric Hosmer was rumored to sign after midnight, but Boras wasn’t contesting his deal. Boras dropped the appeal on 9/22 after Alvarez re-worked his deal, conveniently getting more than Posey, who wasn’t a Boras client.

75. The Pirates lose 95 games. The losing streak, at age 16, can now drive.

76. The Pirates lose to Manatee Community College (4/2/2009) – This kind of stuff happens on occasion. You put a minor league team or a list of non-roster invitees out there to face a college team in the early part of Spring Training, and occasionally that college team will win. They’re not beating the Pirates, even though the team playing is called the Pirates. It was an embarrassing moment, especially when the Pirates were entering the year where they could set the record in professional sports for the most losing seasons in a row.

77. Nate McLouth traded for Charlie Morton, Jeff Locke, and Gorkys Hernandez (6/3/2009) – The trades by Huntington in 2008 didn’t have a long-lasting effect. This deal marked the turnaround. I remember seeing a lot of people talking about how this deal would make or break Huntington’s career. He traded McLouth, a young player coming off a breakout season, who was signed to an extension the previous off-season. He got a return of players that wouldn’t fully help the team for a few years, signaling that the Pirates weren’t going to be competing any time soon. The Pirates ended up selling high on McLouth, and as we’ve seen this year, Morton and Locke have helped in the long-term. After years of seeing Littlefield and Bonifay refuse to go all-in on the rebuild, it was good to see Huntington make that tough call.

78. The 2009 draft (6/9/2009) – The Pirates passed over a group of prep pitchers to take Tony Sanchez, then went heavy on over-slot signings with the money they saved. Some of the prep pitchers included Shelby Miller and Jacob Turner. A few other teams passed on those guys, mostly because all of the prep pitchers were asking for big money, and no one really stood out. Had the Pirates gone for one of the prep pitchers, they wouldn’t have necessarily ended up with a better result. They could have easily gotten Tyler Matzek. This draft has produced some players (Vic Black, Brock Holt, Phil Irwin, and of course Tony Sanchez), but it lacks any impact. When paired with the slow-to-succeed 2008 draft, this had people questioning Huntington’s drafting abilities for a few years. There were also questions of whether the Pirates were left scarred by the Alvarez/Boras situation the year before. Those still come up for some reason, even though the Pirates have since drafted tough to sign Boras clients.

79. Pirates acquire Joel Hanrahan (6/30/2009) – The Pirates traded Nyjer Morgan and Sean Burnett to the Nationals for Lastings Milledge and Joel Hanrahan. The deal was a classic buy low/sell high move. Milledge had upside, but was struggling in the majors. Morgan didn’t have a ton of upside, but established himself as a good player. To make up for the difference in value (and to tilt the scale in Washington’s favor), a second swap of Burnett and Hanrahan was added. This was one of the first moves where Huntington took a reliever who was dominant, but at a low point, and turned him around. Hanrahan was almost immediately a good reliever again, and has since been the best player in this deal.

80. Miguel Sano signs with the Twins (9/29/2009) – The Pirates had the inside track on Miguel Sano, but an age investigation delayed any team from being able to sign him. Throughout the delay, the Pirates tried to sign Sano, and were the top bidders. It was a messy situation that led to a “he said, she said” situation. One side of the story was eventually made into a movie. In the end, the Minnesota Twins signed Sano for $3.15 M, and Sano’s agent, Rob Plummer, didn’t call the Pirates to see if they’d beat the deal. This was after weeks of the Pirates having the top bid with no one stepping up, and Plummer wanting them to bid against themselves and pay more. In hindsight, they would have had Sano if they offered less than a million more. But if we play the hindsight game, they’d be able to know that Plummer wouldn’t let them beat another team’s offer if another team outbid them. All in all, it was a messy situation where we probably will never hear the true story, but instead will hear two versions of what was true.

81. (2009) The Pirates lose 99 games, setting the professional sports record for 17 straight losing seasons.

82. Pirates lose 20-0 to the Brewers (4/22/2010) – The Pirates struggled against the Brewers for years, and no loss was worse than this one.

83. Pirates acquire James McDonald/Andrew Lambo for Octavio Dotel (7/31/2010) – At the time the 2009 trades didn’t look as good as they do now. The 2008 trades were starting to look bad, especially with Bautista breaking out. So the McDonald/Lambo deal looked like one of the best moves. The Pirates traded a reliever for two guys who were recently two of the top prospects in baseball, and the top two prospects in the Dodgers system. It might not have the long-term impact, but the Pirates got two full seasons-worth of #4 starter numbers from McDonald, plus whatever they’ll get from Lambo, for Dotel. They also traded D.J. Carrasco, Ryan Church, and Bobby Crosby to get Chris Snyder and Pedro Ciriaco on that same day. More of the “trade relievers for something more valuable than relievers” trend.

84. Pirates draft and sign Jameson Taillon and Stetson Allie (8/16/2010) – In the previous season the Pirates went signability in the first round, and passed up a lot of prep pitchers. In 2010 they took the top prep pitcher, and also took Stetson Allie, who fell from the first round to the second round. They went over-slot on Taillon, and went way over-slot for Allie. They also got Nick Kingham in this draft in the fourth round, and took Brandon Cumpton in the ninth round. Kingham emerged as a top prospect, while Cumpton made four starts for the Pirates this year.

85. Luis Heredia signs (8/19/2010) – This was like the Sano situation was expected to go. The Pirates had the inside track on Heredia. They were expected to sign him, although other teams were interested. Because of the Sano situation, people figured the Pirates wouldn’t land Heredia. Then, a few hours after he was eligible to sign, he signed.

86. (2010) The Pirates lose 105 games, for their worst season during the streak. That extended the losing to 18 years.

87. The 2011 draft (6/6/2011) – It’s still early, but this might be one of the best draft classes in Pirates history. They drafted first overall, and took Gerrit Cole, who has the upside to be an ace. In the second round they took Josh Bell, who fell after sending a letter to every team telling them not to draft him. The Pirates ignored that, gave him $5 M, and signed him, while breaking the draft signing system in the process. They also got Tyler Glasnow for $600,000, Clay Holmes for $1.2 M, Alex Dickerson for slot in the third round, and other promising prep pitchers like Jason Creasy, Jake Burnette, and Colten Brewer (the latter two have been injured too often). It’s possible the Pirates could get two aces out of this draft, without considering what Bell, Dickerson, Holmes, or anyone else could do.

88. Pirates originally sign Jason Grilli (7/21/2011) – The Pirates were surprisingly contenders, looking to upgrade in late July. Jason Grilli was having a good season in Triple-A for the Phillies, and had a clause in his deal allowing another team to sign him. All that team had to do was offer him a major league deal. The Phillies could either put him on the active roster, or release him. They chose to release him, and the Pirates ended up getting a huge steal, and a key piece to their turnaround.

89. Jerry Meals (7/26/2011) – The Pirates played an epic 19 inning game against Atlanta, which ended with a horrible blown call at the plate by Jerry Meals. It ruined a game that otherwise would have been remembered for a little girl shouting “Let’s go Pirates” non-stop from the outfield, a group of fans stacking every beer cup in a section and running around with a tower of cups, and Daniel McCutchen playing the game of his career. Instead, it’s remembered for this:

90. Pirates add Derrek Lee and Ryan Ludwick at the trade deadline (7/31/2011) – The Pirates didn’t necessarily make a huge splash, but they added some good, low-cost options. That was good, since they really weren’t in position to be trading prospects away to go for it that year. Lee hit two homers in his debut, drawing comparisons to Shawon Dunston. A few days later he tried to block a pitch with his hand, broke his hand, and missed a month. Ludwick didn’t performed as expected, at least not until the following year with Cincinnati. This was the first time the Pirates had been buyers at the trade deadline in a long time.

91. (2011) The Collapse. The Pirates were seven over .500 in mid-July, and in first place. They finished the season 72-90, going 18-38 from August to the end of the season. This was year number 19.

92. A.J. Burnett acquired from the Yankees (2/19/2012) – You had to know things were starting to go the Pirates way when the Yankees started salary dumping players to Pittsburgh. Burnett was traded for Exicardo Cayones and Diego Moreno, and the Yankees picked up half of his salary. Once free of New York, Burnett immediately returned to look like a top of the rotation pitcher. He also became the leader of the pitching staff, and one of the key veteran leaders of the team. This might have been the single most important move for the turnaround.

93. Andrew McCutchen signed to an extension (3/5/2012) – One thing that other small market teams were doing was signing young players to big extensions, buying out free agent years in the process. This could be risky, as seen with the Jose Tabata extension. On the flip side, it could be a huge value, which was the case with McCutchen. At the time, fans were talking about when McCutchen might be traded. One year before free agency (which was set following the 2015 season). Two years to get more value? Three years to avoid paying him anything because Bob Nutting is cheap? By the way, the two year would have been this coming off-season. Instead, the Pirates extended McCutchen to a deal giving them control through the 2018 season, with $51 M guaranteed.

94. Mark Appel doesn’t sign (7/14/2012) – Under the new draft system, which restricted spending, the Pirates saw top prospect Mark Appel fall to them with the eight overall pick. They took him, and instead of signing, Appel went back to Stanford. It might work out in the end, as Austin Meadows (the comp pick for Appel) is off to an amazing start. The narrative around Appel this year has been that the deal hurts the Pirates because Appel would have allowed them to trade Jameson Taillon at the deadline. Never mind that there was no one actually available at the deadline in 2013 to trade Taillon for. Also, the only way to sign Appel is to forfeit the first and second round picks of the next two drafts. That means no Meadows, Reese McGuire, or Blake Taylor, plus whoever the Pirates take with the first two picks next year. No player is worth that much.

95. The 2012 trade deadline (7/31/2012) – For the second year in a row, the Pirates were buyers. This time they actually traded from the farm system to get Wandy Rodriguez. They also traded for Gaby Sanchez and Travis Snider. The moves were criticized because the Pirates added guys who were under control beyond the 2012 season, but weren’t as big of names as some of the other available options who were free agents after the season. This led to people saying that the Pirates finally added at the deadline in 2013, all because they got pending free agents, even though they had added at the deadline the previous two years.

96. (2012) The Collapse II. This features a ton of moments that we’re going to sum up in one depressing number. The Pirates went from 16 over .500 on August 8th to a 79-83 record. They finished the season 16-36. September was the worst, not just because of their 7-21 record. That month featured a seven error game (9/7/2012) and a Homer Bailey no hitter (9/28/2012). This is where Harvey Dent would say “The night is always darkest before the dawn”.

97. The amazing 2012-13 off-season (November 2012 – January 2013) – The Pirates had an amazing off-season coming into the 2013 season. This wasn’t collusion fueled. It was just great move after great move. They out-bid the Yankees to get Russell Martin, providing a huge upgrade at the catcher spot. They traded Joel Hanrahan and Brock Holt for Mark Melancon, Stolmy Pimentel, Jerry Sands, and Ivan De Jesus. Just the Melancon part makes that trade a win. They signed Francisco Liriano to a two-year deal, which in total looks like it would be a steal just for one year. Even the smaller moves were great, as they got Vin Mazzaro and Jeanmar Gomez for next to nothing.

98. The 2013 draft and the recognition of the farm system (6/6/2013) – The Pirates have been building up their farm system for a few years, but people really took notice this year. Not many players stepped back with their development. Meanwhile, for the second year in a row the Pirates had one of the biggest breakout players in baseball. In 2012 it was Gregory Polanco and Alen Hanson. In 2013 it was Tyler Glasnow. Then there was the 2013 draft class. The Pirates landed two top prep hitters in Austin Meadows and Reese McGuire. They also drafted for a lot of upside in the middle rounds. The 2013 draft has a long way to go to match the 2011 draft, but it’s looking like a strong group out of the gate. The overall result is that the Pirates have one of the best 1-9 prospects in the game. Our mid-season list: Jameson Taillon, Gregory Polanco, Tyler Glasnow, Alen Hanson, Austin Meadows, Josh Bell, Nick Kingham, Luis Heredia, Reese McGuire. All of those guys have the potential to be impact players at their position. They all would have challenged for the top spot in the system during the majority of the years during this losing streak.

99. Pirates trade for Marlon Byrd, John Buck and Justin Morneau (late August 2013) – The non-waiver trade deadline was quiet, but the Pirates were busy at the end of August. They made a big splash by trading top infield prospect Dilson Herrera and top relief prospect Vic Black for Marlon Byrd and John Buck. As I mentioned before, they had traded for help the previous two years. This came with the novelty of trading prospects for rentals, which for some reason is better than trading prospects for a someone who will be around beyond the current season. A few days later they did it again, trading Alex Presley and Duke Welker for Justin Morneau, and taking on all of Morneau’s remaining salary.

100. Win number 82 (9/9/2013) – One year ago the Pirates were in the middle of one of the biggest collapses in baseball history. One year later they posted their first winning season since 1992.


Win number 82 is just a stepping stone. The real goal is contending, and that’s what the Pirates are doing this year. But win number 82 closes a long and dark chapter in Pirates history. For 20 years the Pirates were faced with losing. That time was filled with rebuilding, horrible direction, watching players go on to help other teams with no compensation, bad drafting, no international signings at times, and some of the worst luck you can imagine mixed in. Even a bad and incompetent team is going to have a winning season once in 20 years. The fact the Pirates were bad for so many years was a reflection on them, but the fact that they didn’t have a fluke winning season and actually had this streak was misfortune. Not that 82 wins in 1997 or 1999 makes any of this better.

The Pirates are clearly coming out of it now. They’re contenders, with a team that will largely be together beyond the 2013 season. They’ve got one of the top farm systems in the game, with several impact prospects set to join the team next year. Any concerns that they won’t spend on a winner, and don’t know what they’re doing, should be put to rest by now. I don’t know if they’re TBMTIB, but this turnaround was no accident. If you read through this massive recap of the last 20 years, you’ll see that the previous groups weren’t fully committed to building the right way. The current group didn’t do everything perfectly, but they had a clear plan to actually commit to rebuilding. The end result is that the Pirates are successful this year, and set up for a good chance at being successful for years to come. There definitely won’t be any long losing streak coming up.


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