Jon Lester signs with Chicago Cubs for 6-year, $155 million contract

3-time All-Star and two-time World Series Champion Jon Lester will be a critical part of the Chicago Cubs rebuilding process.

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The Chicago Cubs have not been to the World Series since 1908 and have not been favored to go back for a very long time. But that might change this year with the addition of the highest-value free agent pitcher this season.

Pitcher Jon Lester agreed to a six-year, $155 million contract late Tuesday to become a key asset in the Cubs’ rebuild. Cubs manager Joe Maddon spoke about it in the lobby of the Manchester Grand Hyatt at the winter meetings.

“It’s not often you get to win the lottery,” Maddon said. “And we won the baseball lottery so far this year; but now it’s up to us to put it into effect. It’s all theory right now. We’ve got to make it real. But you need pieces like this to make it real.”

Lester, a left-hander who turns 31 next month, chose the Cubs over the Boston Red Sox, which bid six years and $135 million to bring him back to Fenway Park after trading him to Oakland last July. The San Francisco Giants were also a serious suitor for Lester, at six years and $150 million. But the Giants would not go to seven years, and the Cubs’ deal was said to include a vesting seventh-year option.

Lester helped the Red Sox win two World Series titles in 2007 and 2014. He is a 3-time MLB All-Star, and has ranked in the top 10 for wins in six of his last seven seasons.