Early Wednesday morning, sought after free agent ace, Jon Lester signed a 6 year $155M contract with the Chicago Cubs choosing them in favor of his former team, the Red Sox.
After months of deliberations, meetings, offers and false reports, a 30 year old Lester became the fourth highest paid player in baseball with his blockbuster contract. The deal, which will run through the 2020 season, involves a $30M signing bonus spread out over the contract and a yearly base salary that will not change from season to season. At the end of year six of the contract, the Cubs will either have the option to invoke a $10M buyout on Lester or a $25M vesting option in the event that he pitches 200 or more innings in 2020.
Among the other contractual courtships that the Cubs contract grants Lester are a guaranteed 25 hours of personal flying time on a private jet each calendar year and a no trade clause.
The $170M that the Cubs contract makes available to Lester was enough to make the Red Sox offer appear obsolete and halfhearted to many fans.
The final offer from Boston (while not as definitely fleshed out details wise as the actual deal Lester signed) appeared to have clocked in at $135M. Furthermore, it lacked the no trade clause that Lester, a family oriented man, has expressed desire to have.
While Lester has said many times over that he would be willing to take a hometown discount, the $20M discrepancy between the Boston and Chicago contracts in guaranteed money seemed to be too much.
He needed more from Boston if he was to return.
In the end though, the Red Sox were simply unwilling to dish out that extra mouney especially after committing nearly $200M to Hanley Ramirez and Pablo Sandoval last month.
"We had a pretty clear idea internally where we were willing to go in the offseason and we had an opportunity to go there," GM, Ben Cherington said. "What we didn't know is where the market would go. In free agency there's always a chance the market gets past where that line is. In this case it did."
The official signing at 1AM Wednesday and the Tuesday night call to management that preceded it signified a somewhat awkward end to a nine year career in Boston that won Lester two World Series rings.
Following it, there was budding animosity felt by Sox fans towards the greater debacle of the past month. Among the poster children for that anger were and still are the faces atop the Red Sox managerial ladder.
Going back to last spring, the team seemed to show apparent disrespect towards their long tenured ace. They offered him multiple small money contracts that were at times over $50-70M less than the one he just signed. As he rejected each contract, they vilified him in their interactions with the media almost attempting to portray him as someone less than the professional that he was.
The damage done in the preseason seemed to hurt the Red Sox’ chances with Lester as the team and him entered the negotiation process.
But at the same time, such rationalization for the departure of a Boston legend could be overthought.
Rather, Lester, a possible future hall of famer, a man who had already won a pair of Championships, a three time all-star and a resilient man who beat deadly cancer of the blood years ago could very well have gone to the team that offered him the money he deserved.
Jon Lester loves Boston. But the Cubs are willing to love Lester. And even if they bought his love, Lester will likely pitch as good or better than he did last season. In doing so, he will instantly make the Cubs a team, infinitely better than the one they fielded a year ago.
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