Jon Lester is the newest Chicago Cub. The Cubs landed the free agent southpaw on Tuesday night, handing him a six-year contract worth $155 million to be their new staff ace. Chicago is a team on the rise and Lester will be at the forefront of the next great Cubs team.
Meanwhile, the Red Sox are left to pick up the pieces. They tried to sign Lester to a long-term extension back in spring training and, even though they traded him away at the deadline, they tried to sign him this off-season. They fell short and now have to look elsewhere to try to fix what might be the worst rotation in MLB.
Although they tried to sign Lester and told anyone who would listen they wanted him to finish his career in Boston, the offers show the Red Sox were never really serious about keeping him around. At least not at anything but a steep discount. Their extension offer in April was a major low-ball:
The Red Sox's most recent offer to Lester was far below market value -- four years between $70 million and $80 million, according to sources within the team's clubhouse.
Lester, who is eligible for free agency at the end of the season, rejected the offer and will not resume negotiations with the club until the off-season, the sources said.
That's less than half the guaranteed money Lester will get from the Cubs. Four years and $70-ish million is A.J. Burnett and C.J. Wilson money, not ace money. Now, to be fair, Lester did say he was willing to take a "hometown discount" to remain in Boston back in January ...
“I want to be here until they have to rip this jersey off my back. As a player it’s good for baseball,” Lester said, “I want to win and if that means taking a (Dustin) Pedroia deal where you stay here for less money to be happy and be competitive and win every year, let’s do it. Let’s get it done.”
... but that offer was beyond a hometown discount. That's not even something Lester and his agent could take seriously. I won't call it an insult because hey, 70 million-plus is a ton of money, but that was not a realistic offer. It couldn't even function as a starting point for negotiations. It was unworkable.
Contract talks were cut off, Lester was traded, and then he hit free agency. As soon as he was traded, Boston's chances of keeping him went down. They forfeited the opportunity to conduct exclusive negotiations, meaning they would have to compete for him in a bidding war with other deep pocketed teams.
As mentioned before, Lester took six years and $155 million from the Cubs. Here is the Red Sox's final offer, according to our own Jon Heyman:
red sox offered $135M, 6 yrs. as @JeffPassan said
— Jon Heyman (@JonHeymanCBS) December 10, 2014
The same term but $20 million -- $20 million! -- less in guaranteed money. That's over a $3 million per season difference between the two offers.
How could Lester look at those two offers and seriously consider taking Boston's? I know, I know, it's not all about the money and if his heart were truly with the Red Sox he would go back, blah blah blah. This isn't a one-way street. The team has to show the player some love too and the Sox didn't. Loyalty has to work both ways.
Why did the Red Sox behave this way with their homegrown ace? Who knows. Maybe they overestimated how much Lester enjoyed his time in Boston. Maybe they were overconfident in their drawing power as a place players want to play. Maybe they simply didn't want him back and were only pursuing him for positive PR.
Either way, the offers show the Red Sox were never all that serious about keeping Lester in Boston. They low-balled him right to the very end and as a result he's heading to the Cubs. Actions speak louder than words, and the way the Sox handled the negotiations sends the message that Lester was not a priority.
