Major League Baseball

Lester, Cubs ready to end franchise's century-plus drought

Published Dec. 16, 2014 4:54 a.m. ET

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Jon Lester insisted there's no reason the Chicago Cubs can't contend next year and even capture their first World Series title since 1908, around the time the Model T was rolling off the assembly line.

''I'm going in with the intention of winning in 2015,'' he said.

The Cubs are, too.

''This signing really marks the start of a transition for the Cubs, the start of a period where we are clearly very serious about winning the World Series,'' President of Baseball Operations Theo Epstein said Monday, when the team and Lester finalized a $155 million, six-year contract. The deal, agreed to during the winter meetings last week, set baseball records for largest signing bonus and biggest upfront payment.

Chicago hired one of the game's top managers in Joe Maddon, then added Lester, a three-time All-Star who won two World Series with Boston.

''We're not hiding the ball,'' Epstein said. ''The fact that we haven't won in so long helps define who we are. ... I think it attracts players who aren't afraid of that challenge and want to be here for the right reasons. It definitely attracted Jon Lester.''

Lester receives a record $30 million signing bonus, of which $15 million is due by April 1, $2.5 million each by Dec. 31 in 2018 and 2019, and a final $10 million installment by Sept. 15, 2020.

He gets salaries of $15 million next year, $20 million each in 2016 and 2017, $22.5 apiece in 2018 and 2019 and $15 million in 2020. There is a $25 million mutual option for 2021 with a $10 million buyout, and the option would become guaranteed if Lester pitches 200 or more innings in 2020 or 400 or more in 2020-21 combined.

Lester's deal includes a hotel suite on the road, a provision that he can't be traded without his consent and the right to 25 hours of private-plane use for him and his family annually.

His wife and two young children joined him at Restaurant Spiaggia along with other family members and agents Sam and Seth Levinson. His 4-year-old son Hudson took a seat on his lap during the news conference.

The no-trade clause is a break from the norm for Epstein. He said the Cubs initially resisted but conceded because it would have been difficult to land Lester without one, particularly after he was dealt from Boston to Oakland last July.

Epstein also acknowledged the deal carries a risk for the Cubs, considering Lester turns 31 next month.

''I know exactly what shoulder program he's been on since he was 18,'' Epstein said. ''I know how well he's executed that shoulder program. How diligent he's been. I know what his MRIs look like. I already signed him to a contract extension in the past; that comes with MRIs. His work ethic didn't change one bit. His passion didn't change one bit after signing that first contract.''

The fact that he's a lefty is another plus to Epstein, and he thinks Lester can pitch well deep into his 30s like former Yankee Andy Pettitte.

''Left-handed pitchers in this bucket tend to perform throughout their contracts better than right-handed pitchers,'' Epstein said. ''He's got the right amount of pitch mix that will allow him to age gracefully because he doesn't get hitters out just one way.''

A total of 1,686 players have appeared for the Cubs since Orval Overall retired Detroit's Boss Schmidt for the final out of the 1908 World Series, according to STATS, and all have failed to bring another title to the North Side.

Lester hopes he and a promising core of young players can end the slide along with Maddon, who left Tampa Bay for a $25 million, five-year contract with the Cubs.

''When you make a statement like bringing in Joe Maddon, that adds to the decision-making, makes it that much more interesting,'' he said.

Lester went 16-11 with a career-best 2.46 ERA and 220 strikeouts last season and is 116-67 with a 3.58 ERA in nine big league seasons. He also had been sought by the Red Sox, World Series champion San Francisco and the Los Angeles Dodgers.

Lester is headed to a team that hasn't made the playoffs since 2008, but he knows Epstein, general manager Jed Hoyer and senior vice president of player development and amateur scouting Jason McLeod from their time together in Boston. He had a chance to talk to pitchers Jeff Samardzija and Jason Hammel about the Cubs after they got traded to Oakland. He also spoke with Ryan Dempster, his teammate in Boston and now a member of Chicago's front office.

Lester will be joining a rotation that includes Hammel, who agreed to a $20 million, two-year contract last week. The Cubs also acquired two-time All-Star catcher Miguel Montero from the Arizona Diamondbacks at the winter meetings and have a pending $4.5 million, one-year agreement with reliever Jason Motte.

Lester has worn No. 31 for most of his career, but the Cubs retired that number in honor of Greg Maddux and Fergie Jenkins. He'll wear Kerry Wood's old No. 34 in Chicago - with Wood's blessing, according to Epstein.

''It's always been one of my favorite numbers other than No. 31,'' said Lester, who pointed out that Nolan Ryan and Chicago Bears great Walter Payton also wore 34. ''I just feel like it was a good fit.''

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