Jon Lester Joins Cubs

Prized free agent Jon Lester agreed to a six-year, $155 million contract with the Chicago Cubson Tuesday, sources told Yahoo Sports, launching the upstart Cubs’ return to the high-end free-agent market and rewarding the 31-year-old left-hander with the second-highest average annual salary ever for a starting pitcher.

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Jon Lester is coming off the best season of his career. (Getty Images)

The Cubs emerged victorious in a ferocious bidding war that included the San Francisco Giants, who had agreed to offer Lester a seven-year deal for around $168 million, and Lester’s longtime team, the Boston Red Sox, who were runners-up after a final offer of six years and $135 million, according to sources. The Los Angeles Dodgers entered the foray late in the process, too, and presented an offer similar to the Cubs’, but Lester chose to reunite with Chicago president Theo Epstein and general manager Jed Hoyer, the executives who drafted him in Boston.

Throughout the process, Lester was tugged in all different directions. Toward the Northeast, where his fond memories of two World Series victories with Boston carried great sentiment despite a lowball contract offer last spring that ultimately led to his trade to Oakland over the summer – and the free agency that turned him into one of the highest-paid pitchers ever. Toward the West, where the Giants, champions three times in the last five seasons, nearly poached Lester with the allure of their success. Even toward the South, where the Atlanta Braves could have made a run at Lester, who lives about 20 minutes from the site of their planned stadium and liked the idea of staying home.

Ultimately, he went to the North Side of Chicago, where he’ll join a reinvigorated franchise intent on winning its first World Series in more than 100 years. The young core put together by Epstein and Hoyer is unmatched in baseball, from first baseman Anthony Rizzo and shortstop Starlin Castro – youthful veterans with incredibly team-friendly contracts – to the swell of prospects on the come: third baseman Kris Bryant, shortstop Addison Russell, outfielder Jorge Soler, second baseman Javier Baez, utilityman Arismendy Alcantara, catcher Kyle Schwarber, outfielder Albert Almora and more.

The Cubs’ familiarity with Lester led them to bump their first offer of six years and $135 million up to $155 million – with a seventh-year vesting option – which puts Lester below only Clayton Kershaw in terms of annual salary among pitchers. He’s expected to start the first game of the major league season, a Sunday night affair against the St. Louis Cardinals on April 5, and front a rotation that includes breakout star Jake Arrieta, Kyle Hendricks, Tsuyoshi Wada and the just-signed Jason Hammel.

“I want to feel wanted,” Lester said at the outset of free agency. “I want to go to a place that appreciates what I do on the field and off the field, as far as with our charitable work, how we represent the team in the community.”

Over his nine years in Boston, Lester was a paragon in both areas. After beating lymphoma at 22 years old, he returned to win the clinching game of the 2007 World Series. He pitched even more brilliantly in the 2013 postseason and won his second championship before turning in his best year as a professional in 2014: a career-high 219 2/3 innings with a 2.46 ERA between Boston and Oakland.

Jon Lester 2014 ERA and Runs Allowed | FindTheBest

All the while, Lester became a great ally of the pediatric cancer community with the NVRQT campaign. During meetings with teams, he stressed the importance of his charity work. The Cubs’ emphasis on it during their mid-November meeting – while most of his other get-togethers included strictly ownership and baseball-operations people, Chicago brought in community-relations personnel – stuck with Lester, as did the straightforwardness of Epstein and Hoyer.

“The thing I liked about ’em is it wasn’t forced and wasn’t a sales pitch,” Lester said after his meeting with the Cubs. “It was like, ‘This is what we can do.’ I don’t want BS. I don’t want show. I don’t want glitz and glamour. I don’t want to walk out to the field with your name and number on the JumboTron. I’m not 18 anymore. I want you to tell me what you can do for me and my family.”

Over the final days of negotiations leading up to this week’s Winter Meetings, the bidding turned feverish. Boston owner John Henry flew to Atlanta for a meeting with Lester, trying to personally persuade him to return to Boston after the team bungled its negotiations with him last season by offering a four-year, $70 million extension. San Francisco added the seventh year, a potential trump card, especially after Giants brass and franchise player Buster Posey wowed Lester during a meeting at his home.

Lester ached over the choice, aware each came with benefits and detriments. He made lists with pros and cons, talked it over with his wife, Farrah, and decided on a new home: the renovated Wrigley Field, rich with history and ready for him to make even more.