Now, his 2011 season is over before it even starts because he will be undergoing Tommy John surgery.
Even though Lackey did not pitch well during his time with the Red Sox, the team will need to find a way to replace him this winter.
On top of this, the Red Sox will also need to deal with Tim Wakefield's impending free agency as well. Here are five players Boston can acquire to replace the abundantly disappointing John Lackey,
This one is likely a long shot, but it would be a huge move for the Boston Red Sox. After the disappointment of their horrible collapse, the Red Sox may be looking to do something big this winter.
C.C. Sabathia will be opting out of his contract, and if the Red Sox are able to sign him, they will have pulled a massive coup.
In one swift move, the Red Sox will have made themselves significantly better while also making the rival New York Yankees significantly worse.
The Boston Red Sox have experience with the Japanese posting system from Daisuke Matsuzaka. However, this might also make the Red Sox hesitant about going after Yu Darvish.
Darvish has been absolutely dominant in Nippon Professional Baseball, but that does not always translate into success in the States. One advantage that Darvish has is that he has performed well against international competition as well.
Boston may choose not to go after Darvish because of his price tag. However, if they have the money to go after Sabathia, there is no reason that they could not sign Darvish.
When the Red Sox traded for Erik Bedard this summer, they knew he would be a free agent in the upcoming offseason. After the news about John Lackey, the Red Sox likely have more interest in re-signing him.
Bedard has struggled with injury issues of his own, but he has proven that he is an outstanding pitcher when healthy. He will also be an inexpensive option for Boston.
In the days approaching the trade deadline, the Houston Astros were trying to trade away Wandy Rodriguez. They were not asking for much in return, as they just wanted to dump his salary.
Now that John Lackey is out for the year, the Red Sox may be interested in making a move for Rodriguez.
He has had an ERA under 3.60 in each of the past four season, but he likely wouldn't be able to sustain that in the AL East.
Paul Maholm is one of the best bargains available on the free-agent market this winter.
He may not have the sparkling win-loss record of some of the other pitchers available, but that is more of a product of the team he played for rather than an indication of his talents.
Maholm put together an outstanding season in 2011. While Maholm will never be a front-of-the-rotation stater, he could do a great job in the middle or back-end of the Red Sox rotation.