Top 10 Worst Happenings of the Pirates Futility Streak

It has been seventeen years since the Pirates finished .500. Everyone knows that. Let’s have a look at the top 10 things that contributed to the streak, starting the clock at December 8, 1992. That’s the day that Barry Bonds signed with the San Francisco Giants.

10. Not signing Reggie Sanders to a long term deal in 2003.

Reggie Sanders joined the club for a tidy $1 million for 2003 and then walked as a free agent following a 31 homer year. Had the Pirates signed him to a two year contract – even ponying up more annually to do so – 2004 might have been more pleasant. We were stuck with Randall Simon playing first part time, moving Craig Wilson into RF. What if Reggie Sanders had been there to man right and Craigers spent the whole season at first. Daryle Ward and Rob Mackowiak would’ve been solid off the bench and this club might’ve done better than 72 wins. That happened to be the last time that the Pirates won 70 contests.

9. 1993 Draft

The Pirates walked into the 1993 draft armed with three first round picks. They had one the natural way and received two sandwich picks due to free agent losses (Bonds and Doug Drabek). They walked out of the first round of the draft with Charles Peterson, Jermaine Allensworth and Andy Rice. Peterson had fewer than 10 at bats above AAA. Allensworth was mediocre in his 1,031 ML at bats. Rice spent five seasons in the minors and never advanced passed A ball. Only one other player signed by the Pirates in the 1993 draft appeared in the Show – Chris Peters.

8. Trading Chris Young in 2002

Following the 2002 season, the Pirates sent Chris Young – a 16 game winner in his minor league debut season – to Montreal for Matt Herges. The Pirates released Herges at the end of Spring Training in 2003. While Young posted a 3.46 ERA in 31 starts in 2006, the Pirates gave 19 starts to Victor Santos. This would be tougher to swallow had young stayed healthy. But he has been hampered by the injury bug the last couple of seasons.

7. Trading Jay Bell and Jeff King in 1996

King spent time in 1996 at both first and second. Bell was, of course, the shortstop. The 1997 Pirates came oh so close to winning 82 games even with Kevin Young (1B), Tony Womack (2B) and Kevin Polcovich (SS) all holding their own. Could the presence of King and Bell have pushed the Pirates beyond .500? In exchange for King and Bell, the Pirates got Joe Randa (and left him unprotected in the expansion draft following 1997), Jeff Granger, Jeff Wallace and a career minor leaguer.

6. Jason Kendall’s ankle injury in 1999

It was July 4, 1999. The Pirates entered a game against the Brewers at 40-39. In the fifth inning, Jason Kendall’s ankle essentially exploded as his foot rolled off the side of first base as he hustled trying to beat out a batted ball. Pirate catchers (primarily Keith Osik and Joe Oliver) other than Kendall hit less than .200 in 302 at bats. They scored 22 times and knocked in 23 runs. Pittsburgh finished 78-83. There is a good chance that Kendall was worth four wins down the stretch.

5. Signing Derek Bell in 2000

The Pirates have – deservingly so – taken a lot of grief for signing Bell and paying waaaaay too much. For their $5 million in 2001, the Pirate got numbers that rivaled those of George Hendrick in 1985. Bell accumulated a 48 OPS+ in 183 plate appearances. Operation Shutdown in Spring Training 2002 saw the end of his brief stint in Pittsburgh and his career in general. The 2001 Pirates were doomed anyway and lost 100 games.

4. Releasing Bronson Arroyo in 2003

In February 2003, the Pirates waived Bronson Arroyo. He is 77-69 since then and has pitched 200 or more innings five straight years.

3. 1994 Draft

Exactly one player the Pirates drafted in 1994 made the Majors. That would be Jimmy Anderson. Yikes.

2. Releasing Tim Wakefield in 1995

In April 1995, Tim Wakefield got his walking papers. He has won 175 games since then. Boston – you are welcome.

1. Trading Aramis Ramirez in 2003

The Pirates got spare parts in exchange for Ramirez and Kenny Lofton. They came in the form of Bobby Hill, Jose Hernandez and a career minor leaguer . Ramirez has averaged 29 homers, 98 RBI and a .303 BA in his six seasons in Wrigley. Needless to say, no Pirate third baseman has come close to putting up those numbers.

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