Last winter, Jon Lester said he "absolutely" would offer a hometown discount to stay in Boston. In the end, the reason the lefty ace signed with the Cubs appears as simple as the Red Sox overestimating just how big a discount they could get away with proposing without pissing Lester off.
Lester's deal with Chicago is a reported $155 million over six years, with a potential vesting option for a seventh, and includes a $30 million signing bonus. It was the most money on the table, and significantly so—the Red Sox's final offer was six/$135M, and even that was up drastically from what Boston initially thought would do it.
Here's ESPN's Buster Olney, who minces no words and said the Red Sox "blew it."
The negotiating benchmarks for high-end pitchers entering their last year of free agency were well-established. In the spring of 2012, Matt Cain had agreed to a six-year, $127.5 million deal with the San Francisco Giants — five years and $112.5 million on top of the $15 million that he would make in the last season before theoretically reaching free agency. During the summer of 2012, Cole Hamels, just two months from free agency, got a six-year, $144 million contract from the Phillies.
There was a great deal of anticipation among some of Lester's teammates about the offer to come. The Red Sox had dumped the contracts of Adrian Gonzalez and Carl Crawford and had signed Dustin Pedroia to what was perceived as an incredibly team-friendly contract, and so the players thought that if anybody deserved to get paid big dollars, it was the homegrown horse of the pitching staff, Lester. Other players who knew him well were convinced that if the Red Sox opened with a $100 million offer and worked their way up to $110 million, it would be done, quickly.
The Red Sox offer: $70 million over four years.
Boston has made something of a habit out of squandering re-signings that appear inevitable, usually by seeking for too much of a discount. It's up for debate whether this is good business or bad (three championships probably answer that), but it's clear that Lester was genuinely hurt but the Red Sox's offer.
The Boston Globe reports that Lester "refused to discuss a deal with the Red Sox a couple of different times, including at the All-Star break." By the trade deadline, when Lester was shipped to Oakland, the Boston braintrust believed their chances of re-signing Lester were slim enough to gamble on a season of Yoenis Cespedes as compensation.
Meanwhile, Theo Epstein—who's close to Lester from their time in Boston—played things perfectly. The Cubs' starting bid was the highest, and only went up from there. In the end, it settled at a potential max value of exactly $100 million more than the Red Sox's first offer, a figure that Olney hints wasn't a coincidence.
The Red Sox should be fine. They project to be a very good team, even before diving into a pitching market that's deep in both free agents and trade targets. They have nine figures sitting around that they were willing to spend. And, with a certain rose-colored view, you could argue that the Sox simply weren't willing to overpay for a pitcher on the wrong side of 30. Maybe they didn't lowball Lester; maybe they're just his only suitors who recognized his fair market value. The fun part is, we'll know within six years.