The Chicago Cubs have won the Jon Lester sweepstakes.
Lester has agreed to a six-year, $155 million contract with the Cubs, according to multiple reports. The deal reportedly also includes a $15 million vesting option for a seventh year.
Lester’s contract carries a $25.83 million average annual value, which is the highest AAV ever given to a pitcher on a multiyear deal in free agency. Clayton Kershaw’s contract carries a record $30.7 million average annual value, but the Los Angeles Dodgers ace signed an extension back in January before ever hitting the open market.
The Boston Red Sox, who were the runners-up for Lester, reportedly submitted a final offer of six years and $135 million. Sources told Yahoo! Sports’ Jeff Passan that the San Francisco Giants, who were eliminated from the sweepstakes Tuesday night, had agreed to offer the left-hander a seven-year deal worth around $168 million. The Los Angeles Dodgers reportedly joined the pursuit late and offered a contract similar to the one offered by the Cubs.
Lester has some familiarity with the Cubs organization. President of baseball operations Theo Epstein, general manager Jed Hoyer and senior vice president of scouting and player development Jason McLeod — all former Red Sox executives — built relationships with the pitcher during their days together in Boston.
Lester, who spent eight-plus seasons with the Red Sox before being traded to the Oakland Athletics in July, clearly had a difficult decision to make. He was drafted by the Red Sox, battled cancer in Boston and helped bring two World Series titles to one of baseball’s most storied franchises. The connection was strong.
Now, Lester will embark on a new challenge, as the Cubs are looking to end a 106-year World Series drought.