John Lackey and Four More Free-Agent Busts for the Boston Red Sox

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COMMENTARY | Through three innings Tuesday night, Boston Red Sox starter John Lackey finally looked like the player that the team shelled out $82.5 million for in December of 2009. He made quick work of almost every batter he faced, providing a much-needed quality outing by a pitcher not named Clay Buchholz or Jon Lester.

And then, in true Lackey-esque fashion, he collapsed as only he could, not even making it out of the 5th inning.

Sights like these have been all too common during Lackey's tenure in Boston. His numbers since signing his deal have been among the worst in his career, with 2011's 6.41 ERA and 1.619 WHIP marking his worst as a pro by far. On top of this, he can't stay healthy. He missed the entire 2012 season with Tommy John surgery and has already served one tour on the disabled list in 2013.

At nearly $16.5 million per year, the Lackey era has not nearly been worth it. But is he the worst free-agent signing for the Red Sox?

Here are four others he has to "compete" with:

Carl Crawford

Despite the $142 million price tag, Crawford brought a lot of excitement to Boston when he signed in December 2010. Fans were quite familiar with him from his days in Tampa Bay and this two-pronged addition didn't just bolster the Red Sox's lineup, it weakened a divisional rival.

Well, theoretically it did. As Boston became the first team in MLB history to blow a 9-game September lead in 2011, Tampa Bay proved that Crawford was no real loss and made the postseason anyway. Crawford's time in Boston was highlighted by injuries and a loss of the speed that had thus far defined his career. Just days after undergoing Tommy John surgery, he was shipped across the country to the Los Angeles Dodgers, ending his Boston career with just 23 stolen bases in 2 years.

Julio Lugo

After bouncing around three teams during his first six major-league seasons, one would think that "buyer beware" would be attached to any contract discussions with Lugo. Not so for the Red Sox, who picked him up for $36 million over four years.

Lugo was a leadoff hitter who couldn't get on base and a shortstop who turned errors almost as often as double plays. His 0-for-31 slide in the first year of his contract didn't endear himself to management, and he found himself in and out of the lineup before he was designated for assignment and eventually traded. He would go on to play for three different teams in the next three years.

Edgar Rentería

Rentería was another that came in with high expectations and ended up disappointing fans in crunch time. Though he scored 100 runs, his average was the lowest in a span of 7 years and he managed just three hits in the 2005 ALDS against the Chicago White Sox. If he hadn't committed enough errors to make Julio Lugo look like a defensive stalwart--30--Sox fans may have overlooked his batting deficiencies. He lasted just one year despite being promised $40 million over four.

Daisuke Matsuzaka

The Matsuzaka circus got off to its three-ringed start before he had even left his home country. The Red Sox bid just over $51 million solely for the right to talk to the 26-year-old, nearly $20 million more than the losing bid and reportedly several times the entire payroll of Matsuzaka's NPB team.

Matsuzaka couldn't possibly live up to those types of expectations. And, for the most part, he didn't. After a solid first two years highlighted by a Game 7 ALCS win in 2007, Matsuzaka's career took a nose dive with several stints on the DL and a ballooning ERA that apexed at 8.28 in his last year. From 2009 to 2012, he won a combined 17 starts, one fewer than his 2008 campaign. Needless to say, this was not what the Red Sox paid for.

One common thread that unites each of these players is that they were all signed by former "Boy Wonder" GM Theo Epstein. Though he did partially assemble the team that finally broke the 86-year drought, he was responsible for carelessly throwing money at underachieving players in the years since. As lamentable as some of current GM Ben Cherington's decisions have been--Bobby Valentine--he has not consistently made the same mistakes that Epstein did.

Andrew Luistro has followed the Red Sox for over 20 years.

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