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Free agent Jon Lester has agreed to a $155 million, six-year contract with the Chicago Cubs. The deal contains an option for 2021 that, if it becomes guaranteed, would make the deal worth $170 million over seven seasons.

The $25.8 million average annual value of the deal is the second-highest for a pitcher behind Clayton Kershaw ($30.7 million).

“It’s not often you get to win the lottery, and we won the baseball lottery this year,” new Cubs manager Joe Maddon said. “Now it’s up to us to put it into effect.”

A three-time All-Star who turns 31 next month, Lester won two World Series titles with the Boston Red Sox. Now he joins the Cubs as their ace as Chicago seeks to challenge for the division and beyond after five straight losing seasons.