Jon Lester finally made his decision on Tuesday night. He had four offers on the table, all of which were worth at least $135 million, and he narrowed his choices down to the Chicago Cubs and Boston Red Sox as the day progressed. He ultimately chose a familiar face.

Lester reunited with former Red Sox executives Theo Epstein and Jed Hoyer, who are currently with the Chicago Cubs. The left-hander signed a six-year, $155 million deal to become the ace of the Cubs starting rotation and will join one of the youngest and most talented rosters in the league led by manager Joe Maddon. The contract also has a vesting option for a seventh year that could bring the total value up to $170 million.

Chicago's starting rotation will consist of Lester, Jason Hammel, Jake Arrieta and likely Kyle Hendricks, while a number of others will compete for the final fifth spot. The Cubs made a number of moves this week to help bolster their case for Lester, which include signing Hammel to a two-year, $18 million deal and acquiring veteran catcher Miguel Montero from the Arizona Diamondbacks for two pitching prospects. With a number of notable free agent starting pitcher still available, the Cubs may not be done adding talent from outside the organization.

Lester was the most sought after free agent thus far in the offseason and was garnering interest from the San Francisco Giants, Los Angeles Dodgers and Atlanta Braves as well. The Braves dropped out of the running early on to avoid getting into a bidding war and the Dodgers waited to attempt a late run at the left-hander. The Giants, who were one of the more intriguing destinations, reportedly offered Lester a six-year, $150 million deal, but were willing to give him a seven-year, $168 million contract if he expressed interest in going there, according to Jeff Passan of Yahoo! Sports. The Red Sox notched the lowest bid at six-years and $135 million.

For months it was speculated Lester could land in Chicago once he became a free agent, and now it's a reality after the team's front office made it happen. Epstein and Hoyer are continuing to work to put themselves in a position to win.

"It's not often you get to win the lottery," Maddon said, via this ESPN article. "We won the baseball lottery so far this year, but now it's up to us to put it into effect. It's all theory right now. We've got to make it real, but you need pieces like this to make it real. He's been [to the World Series] before. He understands what it feels like. I want to believe that he could foresee the same thing happening here."

In nine MLB seasons, Lester is 116-67 with a 3.58 ERA and 1.28 WHIP in 252 starts. He has 1,457 strikeouts in 1,596 innings pitched.

UPDATE: Lester will receive a $30 million signing bonus, which is included in the $155 million.