Both incoming Chicago Cubs President Theo Epstein and his replacement in Boston, new Red Sox GM Ben Cherington addressed the local media for the first time today. While Epstein held court at a press conference full of good vibes and prepared statements, it was Cherington’s duty to inform those who cover his team that starting pitcher John Lackey would require Tommy John surgery, and in all likelihood, miss the entirety of the 2012 season.

Whether that’s good or bad news for the Red Sox chances at the American League East title next season is anyone’s guess, but it certainly does put an emphatic emphasis on what Boston will be seeking this off season in the trade and possibly, free agent market.

Roy Oswalt’s agent is currently handing out free high fives for those interested.

As Rob Bradford of WEEI Sports Radio pointed out earlier today, the surgery will also have a major impact on Lackey’s contract with the Red Sox, or more accurately with what Boston will end up owing in luxury tax.

His deal with Boston included a vesting option at the major league minimum (currently $414,000) for a sixth season if he required season-ending surgery on a pre-existing elbow condition. ‬Such an operation‪ would trigger the option, thus making the contract a six-year, $83 million deal — thus meaning that, for luxury tax purposes, his contract is valued at roughly $13.8 million rather than $16.5 million, something that could mean millions of dollars in luxury tax relief to the Sox.

As certain as I am that John Lackey at a discount will be just what the 2015 Boston Red Sox need to push them over the hump, the real issue here is what the extra year on the contract does for the average annual salary, and therefore its implications on what the Red Sox will pay in luxury tax.

Amid multiple personal problems off the field, Lackey’s second season in Boston was the worst of his career. Over 160 innings, the right 33 year old right handed starter put up the worst walk rate, ERA, FIP, xFIP and WAR of his career. Matters didn’t get much better after his team’s disappointing season ended and every one started overreacting to news that Lackey was among the three pitchers who reportedly drank beer in the clubhouse during games.

As criticism was heaped on him in recent weeks for his lack of professionalism, it should be noted that during the Red Sox horrific collapse, Lackey was going out and pitching with a torn ligament in his elbow. I’m not a doctor but I imagine this might have had more to do with him not being at his most effective than daring to drink alcohol between starts.

However, his five, now six year deal with Boston remains arguably the worst contract handed out during the Theo Epstein era.