Except for one horrendous, torturous, all-manner-of-bad-things eighth inning on an October night in Chicago in 2003, Jim Hendry might have a much different résumé.
It's amazing that in baseball, a sport where the most respected statisticians preach large sample sizes and not rushing to judgment—how often do we hear the phrase "it's a grind" in reference to the 162-game season—pennants and World Series are won or lost on the smallest play: Buckner's error, Damon's double steal, Jeffery Maier reaching over the wall to turn a fly out into a home run, or Steve Bartman doing what any of us would have done on any other night, trying to catch a foul ball.
Would the Cubs have won the 2003 NLCS had Moises Alou been able to catch that foul ball? After all, Alou later admitted he wouldn't have been able to make the play, regardless of Bartman's interference. It's impossible to know, but if we accept that Bartman's actions had nothing to do with the Cubs' inability to halt the damage in the eighth, the logical follow through is that the Cubs lost the game because baseball games are hard to win, not because a billy goat had a bad day.
What we might have thought, however, is that in coming so close to making the World Series in 2003, the Cubs would reach that goal at some point in the near term. They did not. The Cubs did not return to the postseason until 2007, and in both that year and the following, they didn't win a single postseason game. The "lovable losers" haven't seen October baseball since. Making the postseason is hard, and a lot depends on luck—just getting a team to stay healthy enough to last all 162 games is a challenge—but one would expect a team with the Cubs' resources for the last nine years to have made better use of them (then again, maybe not).
Jim Hendry's tenure as the general manager of the Cubs is reflective of the notion of that team as perennial underachievers. The Cubs should have been much better than they were; even in the years the Cubs did make the postseason, they should have gone even further. Hendry isn't responsible for all of that (it wasn't Hendry who abused Mark Prior and Kerry Wood to the point of near-uselessness), and there are teams (the Pirates and Orioles, perhaps) who would envy the Cubs' few years of relative success, but again one comes to the conclusion that the Cubs should have been able to accomplish more.
As an example, consider this: Hendry did not directly abuse either the arms of Prior or Wood, but neither did he step in—Dusty Baker, who often considered responsible, did not leave the Cubs until after the 2006 season. Hendry built a team that included sluggers such as Alfonso Soriano and Derrek Lee, which, in this particular case, meant he also built an offense which struck out at the same rate as the average person draws breath. Sabermetric schools of thought preach high on-base skills in a lineup; the mid-'00s Cubs could stand as the antithesis of that ideal (the 2006 edition is among just seven teams since 1995 to draw fewer than 400 walks in a season, and many of the other Hendry teams were not much better). On the other hand, Hendry's love affair with the strikeout also held true for his pitching staffs, as the Cubs often ranked at the top of the league in strikeouts. Carlos Zambrano, Ryan Dempster, Kerry Wood, and even Carlos Marmol are or were known for their strikeout abilities; given the defense the likes that Soriano, Lee or, say, Kosuke Fukudome provided, the strategy to pursue pitchers who did not, in fact, pitch to contact could have worked—if only Wood had not gotten hurt or Zambrano not gone crazy.
How much credit a GM gets for his team's success or blame he takes for its failure should vary because of a host of factors, not all of which are under his control. If ownership ever restricted a GM's access to monetary resources, if ownership felt a need to interfere in player personnel decisions, or if a star player had a non-preventable injury (like being hit in the head by a liner) could all limit a GM's effectiveness.* That said, we know—by looking at payroll tables, linked above—that the Cubs were not shy about spending money, and we know that if a team "gets bit" by an injury bug, there could be a systemic fault. Even if a general manger is not himself responsible for a certain fault, injury or other misstep (like, for example, a Zambrano tantrum), he still bears a responsibility for the consequence. If a team wasn't good enough to win the NL pennant or the World Series, it doesn't matter what the immediate cause was; the GM still has a responsibility to improve his team for the next season.
*I go much more in-depth in the analysis of how to evaluate a general manager in my chapter in Extra Innings: More Baseball Between the Numbers, which you should read, obviously.
Hendry was able to get the Cubs to return to the playoffs in 2007 and 2008, but one can argue that a team with their apparent financial resources should not have hit the valley of the 2004-2006 seasons, nor should they have fallen so far after the 2008 season, regardless of the success of their division's other teams. How did this happen? Consider the dearth of home-grown players on the Cubs' starting lineups over the season: outside of Geovanny Soto, Starlin Castro and Darwin Barney (the latter two being newcomers), there has been little presence of players the Cubs developed on their own. The farm system might be improving, but farm systems take years to overhaul and bear fruit; in this case coming too late to save Hendry's job.
Hendry will now be joining the Yankees as a special assignment scout under Brian Cashman, on a multi-year deal. Unlike the Cubs, the Yankees don't have a billy goat scapegoat (try saying that five times fast) on which to blame their failures; merely missing the playoffs is akin to the eighth deadly sin. Hendry isn't going to be the next Yankees' GM (at least, not in the next three years), so he won't bear the brunt of the responsibility should the Yankees fail in 2012 or immediately after—unfortunately, the corollary here is that if the Yankees are successful, he won't get the glory, either. The difference between running your own team and playing second fiddle for another shouldn't come down to one bungled inning, but when that inning is the difference between a team's first World Series berth since 1945 or yet another year lost to the billy goat, it means everything.