Considering injuries, lack of production, or money eaten in trades, it has to be the Red Sox. Look at the cost of these guys:
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Carl Crawford $ 20,357,142
Josh Beckett $ 17,000,000
John Lackey $ 15,950,000
Kevin Youkilis $ 12,250,000
Daisuke Matsuzaka $ 10,333,333
Bobby Jenks $ 6,000,000
I think that Beckett and Lackey were signed for contracts that seemed reasonable for players at the stages of their careers they were at when they were signed, and Jenks was what I call a 50-50 signing. There was a 50% chance he would return to form and be worth twice what he is being signed for, but a 50% chance he would be worth nothing. A wealthy team can afford to take that gamble. The Red Sox also gambled on Miller, Aviles and Ross this year and have done well with all three. When you go into the bargain bin, you win some and you lose some.
"Disrespecting" Ortiz by signing him to a one year, $14 million contract now looks brilliant. They'll get about fair value for what they paid him but now he is a broken down plow horse, meaning we won't have Ortiz's contract to kick around on this forum next year.
I have criticized the Crawford contract previously here and elsewhere for a few reasons. One is, the sabermetric gurus who produce charts that I have never taken the time to fully fathom were certain that Crawford's hitting pattern was extremely unfavorable to Fenway. I'm not sure how much stock to put into that because of course, he would be pitched different here than he was elsewhere and would presumable make different swing decisions. But the other was, as I saw it, he simply wasn't a $20 million x 7 year value anywhere. He's good, but not that good.
The Youkilis contract was hard to avoid, though I would not have given it to him if had been the GM. He had become the "heart and soul" of what, historically, has usually been a heartless and soulless team, but I really thought that he was already playing above his head and regarded his early career declination to be likely. And as far as I am concerned, Dice-K is costing the Red Sox 18 million dollars because the $50 million posting fee is at least internally expensed over the length of his contract. I remember when he went 18-3, he did it with smoke and mirrors. He became the first pitcher in 100 years to win 15 more games than he lost while giving up over five walks per game.
Fortunately, the Red Sox can and probably will put together a "pre-season" contending team next year without spending much money. Figure that Bailey will be installed as closer any day now, then Aceves becomes a starter, along with Lester, Morales, Doubront and a fifth starter can be anyone: Cook, Bard, Beckett, or even the next reclamation project, as Miller might even want another shot at starting. They've again done well in the bargain bin with Ciriaco, and this other 3rd baseman they recently acquired named Valencia finished third in the Rookie of the Year voting in 2010 and managed to lead his team in RBI last year. He might just have needed a change of scenery.
One other aspect of the Lackey situation is that they had the foresight to add a unilateral, $500,000 2015 option year into his contract to compensate them in case he lost a year to elbow injury, so we will have the name John Lackey to kick around here for years to come.