Jon Lester Agrees To Six-Year Deal With Chicago Cubs

As the second day of the Winter Meetings in San Diego came to a close, multiple teams were still awaiting word from Jon Lester as to whether or not he would be joining them. Of the four finalists, the San Francisco Giants were the first Lester informed were out of the running and the Los Angeles Dodgers soon followed.

That left Lester deciding between the Boston Red Sox, who traded him to the Oakland Athletics prior to last season’s deadline and the Chicago Cubs, where Theo Epstein heads the front office. With the midnight oil beginning to burn, Ken Rosenthal of FOX Sports broke the news Lester agreed to terms with the Cubs:

Sources: Lester to #Cubs.

— Ken Rosenthal (@Ken_Rosenthal) December 10, 2014

According to Jeff Passan of Yahoo! Sports, Lester signed a six-year, $155 million contract:

Jon Lester, Cubs agree on six-year, $155M deal, sources tell Yahoo Sports. Red Sox are runners-up. Their final bid: six for $135M.

— Jeff Passan (@JeffPassan) December 10, 2014

The contract is the largest in Cubs’ history as it eclipses the $136 million contract Alfonso Soriano signed in 2006. Lester’s $25.83 average annual salary is second-most among pitchers behind Clayton Kershaw.

While the Dodgers were mentioned as one of the finalists in the sweepstakes, how serious their pursuit of the left-hander was is unclear. Lester joins Russell Martin and Andrew Miller as players the Dodgers have expressed some level of interest in only to see them sign elsewhere.

In Martin’s case, it was later reported the Dodgers didn’t get in serious talks with the catcher and they were believed to hesitant in signing Miller to a long-term deal. With Lester no longer available and the Dodgers in need of pitching, they could enter the fray for Max Scherzer and James Shields, but both appear to be long shots and signing either would cost the Dodgers their first-round draft pick in 2015.

Furthermore, Scherzer will likely command north of $200 million, which may not be a commitment the Dodgers are willing to make. Other options include trading for Cole Hamels, who may also be targeted by the Red Sox, or signing a second-tier pitcher to slide into the backend of the rotation.

After nine seasons spent pitching in the American League, next year will mark Lester’s first in the NL. He’s a career 116-67 with a 3.58 ERA and 1.28 WHIP. Though Lester reunites with Epstein and Cubs’ general manager Jed Hoyer, who were both with the Red Sox when the southpaw was drafted.