The Red Sox can only blame themselves for losing Jon Lester. After taking his time, evaluating his options, and eventually following his heart, he decided to head off to the North Side. His six-year, $155 million deal with the Chicago Cubs makes him the leader of a long-suffering team on the cusp of becoming a contender.
The $25.8 million AAV of the contract is second only to Clayton Kershaw among pitchers. Despite the payday, though, Lester’s ultimate decision had less to do with money than it did with comfort. He wanted to go to a place where he and his family would be comfortable. A two-hour flight from his Atlanta home to a friendly city and a team with a familiar front office fit the bill.
The Red Sox essentially lost the Lester sweepstakes in March. Their first efforts in trying to extend him consisted of a four-year, $70 million dollar offer. Even at the time it was a lowball offer. And it may have been low enough to keep negotiations from going any further before and during the season and leave a bit of a sour taste in his mouth going forward.
GM Ben Cherington has said since Lester signed with the Cubs, “I think we would have liked to have had more chance for dialogue prior to the season. Why that didn’t happen, maybe there’s more than one reason. I think we can certainly learn from the process. But we desired to have more dialogue prior to the season and made an effort during the season and weren’t able to.”
There’s every reason to believe the Red Sox weren’t able to have that dialogue because Lester and his agents felt there was too far to go to even reach a middle ground. Based on the contract that he ultimately got, they were right. And now Red Sox executives are left trying to save face.
Many at the time felt the offer Boston had made during the spring was an indication that the team didn’t want to extend him long-term. After all, the organization has a policy to not give lengthy contracts to pitchers over the age of 30.
At the same time, though, it is possible Cherington was just setting the table for further talks. The problem may have been that he poorly judged his market. If he thought the two sides would be able to eventually reach an agreement at five years at around $20 million per year, the four-year deal wouldn’t have been an egregious starting point.
But, as Lester went on to have the best season of his career, the potential for that type of deal was gone. So the team was willing to go to six years and $135 million in an open market in hopes of luring him back, which ultimately didn’t work.
So now the Red Sox are left with a light rotation and money to spend. They have since gone out and traded for Wade Miley, who gives them an innings-eating left-hander who is under team control for three years. But he is, at best, a number three.
The team still needs to find two more front-of-the-rotation starters. There are still plenty of free agents available, including two number ones. It’s highly unlikely the Sox will get in the Max Scherzer bidding, which could run in excess of $200 million. However, they could very well make a run at James Shields, who has been a reliable workhorse in Kansas City and Tampa for several years.
The trade market is also flush with options, like Cole Hamels, multiple Reds starters, and maybe even Jordan Zimmermann. With a surplus of outfielders and a growing list of solid prospects, Boston will move some pieces to bring in another arm or two.
But it would be one less pitcher they’d have to worry about if they were able to bring Lester back. Instead, they’re left to wonder what it would have taken to have gotten it done when they had the chance.
