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At the time of his hiring, Epstein was the youngest GM in the history of baseball. But with age comes wisdom and if he were given the opportunity to go back and do a few things differently, I’m sure he would agree that these are a few he wished he would have avoided.

5. Mike Cameron - Earlier this season the Red Sox decided to designate veteran outfielder Mike Cameron for assignment. This announcement signaled the surrender of Red Sox management on Cameron and kicks off this list of forgettable blunders.

In the winter of 2009, Theo Epstein inked Cameron to a two-year, $15.5 million contract to try and fill the gaping hole that was left field for the Sox. With the trade of Manny Ramirez and the failure to re-sign Jason Bay, the move was a peculiar one that obviously has winded up backfiring and yielded minimal results.

During his short stint with Boston, the 38-year-old has suffered a plethora of injuries and has only played in 81 games. His pathetic .219 batting average is laughable and he’s only managed to hit a total of seven home runs and drive in 24 RBIs. 

4. Matt Clement - Some Sox fans may not remember the name, but back in 2004 he signed a three-year, $25 million contract and was projected to be an integral part of Boston’s rotation. The plan went better than expected early on as Clement began the 2005 season 10-2 and made the American League All-Star team. Unfortunately, it was all downhill from there.

Shortly after that all-star appearance, Clement was nailed by a screaming line drive and his psyche and mound skills never seemed to return to him. From that point on  he compiled an 8-9 record and only appeared in 12 games during the 2006 season before eventually pitching in his final game for the Sox on June 14. He ended his Sox career at 18-11 with an underwhelming 5.09 ERA.

3. Julio Lugo - The shortstop position has been a point of much consternation during the Epstein regime and the search to replace Boston favorite Nomar Garciaparra has proven much more difficult than he originally anticipated. However, Theo thought he had found the solution in 2006 when he employed Julio Lugo to man the position.

It was a four-year, $36 million contract and his production certainly did not warrant such a substantial salary. In his four years in Tampa prior to coming to Boston, he showed some promise as he hit .287 with 10 HRs, 53 RBIs and 22 stolen bases. In his entire time with the Sox (266 games), he batted .251 with a meager total of 10 HRs, 103 RBIs and 48 steals. Given his mighty struggles, the Red Sox found themselves in another Mike Cameron situation and ended up cutting him just to watch him eventually be snatched up by another team while Boston picked up the tab.

2. J.D. Drew - Let’s just say that 2006 wasn’t exactly Theo Epstein’s greatest year. The last two players on this list were both signed within that time frame.  J.D. Drew was a number one overall draft pick who never quite lived up to the expectations that follow a prospect of that magnitude.

Although he did have a couple good years prior to signing with the Sox, the five-year, $70 million contract has not been viewed favorably amongst the Fenway faithful. Throughout his Red Sox career, Drew has never played in more than 140 games in any season and has never reached 500 at bats. He hit .222 this year with only four home runs and 22 RBI. Those aren’t exactly the eye-popping stats that would be associated with a corner outfielder pulling in over $14 million a year. 

1. John Lackey - This much-maligned starting pitcher holds the distinct honor of being the only player mentioned on this list who currently remains under contract for the Red Sox.  In the winter of 2009, John Lackey signed a five-year, $82.5 M contract with Boston.  At the time, it didn't seem like a horrible move - and was even celebrated in some circles, due to the fact he had a career record of 102-71 with a respectable 3.81 ERA.

Two years later and fresh off of a season deemed as the worst ever by a starting pitcher in Red Sox history, people aren't as psyched regarding his existence on the Red Sox roster.  The "bull dog" just finished polishing off a 12-12 record with an inconceivable 6.41 ERA.  His stats apparently aren't the only repulsive aspect to his historically inept season as his attitude was reportedly one of the major contributing factors to the collpase in the clubhouse.  The list of the subpar stats is as long as it is depressing.  So rather than recite them and painfully remind Red Sox fans of his awful year, we'll just wrap this up by saying that Mrs. Lackey apparently isn't the only one fed up with his act.

Despite these shortcomings,  it’s very difficult to criticize Epstein too harshly. Even with overpaying Lugo, Dice-K and Drew he managed to field a championship team in 2007 -- his second in four years -- and, in his profession, that is ultimately the only thing that matters. Hindsight is always 20/20, so for whatever few poor decisions have been made, the good decisions have far outnumbered the bad.

His dedication and proven track record make it easy to see why the Chicago Cubs organization would covet such a commodity.  Only time will author the conclusion to this story, but if it ends with Epstein leaving Boston, his time here could only be classified as a job well done.  If he were to some day break the curse that relentlessly haunts the town of Chicago as well, we could be talking about the greatest GM in the history of baseball.

So be careful what you wish for Sox fans.  Irrational criticism comes far too easily during times of adversity.  I know the pain of this season's abrupt ending naturally lends to the desire to assign blame, but just like in the case of Francona, there are very few options out there that could be considered an upgrade.