FORT MYERS, Fla. — Tom Werner still wonders about one who got away, and it's not Mookie Betts.
The Red Sox chairman wishes the Red Sox could've found a way to keep the All-Star outfielder, but he doesn't regret the team's offers, which he considered aggressive.
There is one player he wishes the team had handled differently, though.
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"I go to sleep at night thinking that maybe we could've made another offer to Jon Lester that maybe would've bridged the gap," Werner admitted on Monday. "I think we made (Betts) what we consider fair and generous offers. As John (Henry) said, I think it was all right for Mookie to want to test the market."
The Red Sox botched the Lester negotiations in spring training of 2014, offering the homegrown All-Star left-hander a four-year, $70 million contract. Lester's camp never even countered, believing the gulf between the team's offer and their ask would make them look greedy once it inevitably leaked.
They were probably onto something, because not long ago WEEI's Lou Merloni reported that Red Sox offered Betts a 10-year contract worth roughly $300 million, while the player countered at 12 years and $420 million, a figure the Red Sox simply weren't willing to reach.
"Free agency plays into many decisions clubs like ours have to make," Henry said. "Today's players spend years in the minor and major leagues earning the right to be paid in a free market, earning the right to make choices. They make significant sacrifices to get there and they deserve what they receive."
Things worked out for Lester. He was traded to the A's that July before signing a six-year, $155 million contract with the Cubs. The Red Sox engaged with him that offseason, but fell well short of Chicago's offer, instead entering 2015 with the five aces that turned out to be zero aces en route to another last-place finish.
All Lester has done since is make two All-Star teams, finish second in the Cy Young voting, win at least 18 games twice, and lead the Cubs to their first World Series in over 100 years.
The Red Sox, meanwhile, overcompensated for his loss not once, but twice, first by signing David Price to a record seven-year, $217 million albatross of a contract to replace him, and then by extending ace Chris Sale last spring, despite injury concerns, to avoid a repeat of the Lester fiasco.