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Cubs land Lester! Lefty ace agrees to six-year, $155M contract

SAN DIEGO — The Cubs landed the centerpiece of their offseason plans late Tuesday night, beating out the Boston Red Sox to land All-Star left-hander Jon Lester.

The Cubs and Lester agreed to a six-year, $155 million contract, sources confirmed — the biggest contract in franchise history and the biggest signal yet that the Cubs are serious about competing for a playoff spot next season.

“This definitely propels us into Plan A, which is kind of neat. It’s a big day for us moving forward,” said new Cubs manager Joe Maddon, who saw Lester a lot over the past seven seasons as the Rays’ manager when Lester was pitching for the Red Sox. “It’s not often you get to win the lottery. We won the baseball lottery so far this year. It’s up to us now to put it in effect.

“It’s all theory right now. We’ve got to make it real. But you need pieces like this to make it real.”

The Lester deal culminated a wild Day 2 during baseball’s annual winter meetings. Keep in mind last spring, Lester rejected a four-year, $70 million extension from the Red Sox. Smart move, considering he more than doubled that package Tuesday.

The Cubs’ bid Tuesday was reportedly $20 million more than the last offer from the Red Sox’, who traded their former ace to the Oakland Athletics in July. Another report said the Giants — considered a favorite early Tuesday — offered a seventh year for a total contract worth about $168 million, or about $1.8 million less in annual value than the Cubs’ deal.

Counting the five-year, $25 million deal Maddon signed last month, the signing of Lester — whose pending decision had been the buzz of the meetings for two days — makes it a $244 million offseason for the Cubs already.

That included Monday’s two-year, $20 million deal to bring back right-hander Jason Hammel as a free agent and Tuesday’s trade with the Diamondbacks for All-Star catcher Miguel Montero, who has three years, $40 million left on his contract.

And the Cubs might not be done. Team president Theo Epstein alluded to another deal that could be coming in the next several days, with indications pointing to another bat.

Maddon said he doesn’t know what’s coming next from Epstein’s front office.

“It definitely sends that message, how Theo and the group feels about this particular group [of players],” Maddon said just after midnight Central time, about a half hour after learning of the market-moving decision by Lester.

“But understand we have a lot of young players that have to grow up,” he added, “and we have to do a good job of nurturing that and making it happen as quickly as possible. But having Jon there definitely adds to the flavor and the believability.”


Lester’s deal contains a $15 million option for 2021 that could make the total package worth $170 million over seven years. If that option year becomes guaranteed, Lester’s average annual salary will be $25.8 million, making him the second-highest-paid pitcher behind the Los Angeles Dodgers’ Clayton Kershaw.

Kershaw just completed the first season of a seven-year, $215 million deal that would put his average annual value at $30.7 million, according to the Associated Press.

Lester, who turns 31 on Jan. 7, won two World Series rings with the Red Sox. Boston traded Lester to the Oakland Athletics in July. He went 16-11 with a career-best 2.46 ERA and 220 strikeouts last season for the Red Sox and A’s and is 116-67 with a 3.58 ERA in nine big-league seasons.

Maddon said the Lester deal changes the Cubs as a franchise.

“We’d like to believe that,” Maddon said. “That’s why you do things like this.”

“You can’t have any more respect for a major-league baseball player than we do for him right now.”

The signing is a culmination of a lengthy recruitment process that included a pitch from former Red Sox teammate Ryan Dempster, a phone call two weeks ago by Maddon and multiple conversations with a Cubs front office that oversaw Lester’s rise to prominence in Boston.

That longtime relationship with Epstein, general manager Jed Hoyer and player-development executive Jason McLeod included going through Lester’s cancer diagnosis and treatment in 2006.

Maddon’s not sure of all the factors that went into Lester’s decision.

“From my perspective it’s exciting to be involved in this moment,” he said. “And I’m eager to see what he has to say and why he chose us, and then after that start formulating the plan for the season.”

A plan that suddenly looks significant and promising for the first time in years on the North Side – with a rotation fronted by Lester and Jake Arrieta, followed by Hammel, 2014 rookie success story Kyle Hendricks and whoever wins the fifth spot.

Maddon said the Lester signing adds extra substance to the message he planned to bring to spring training.

“It definitely makes it more believable to everybody else in that room,” he said. “Because I’ll stand up and make the same speech regardless, but when you have it backed up by that particular kind of presence, it adds to it. I can’t deny any of that.”