Jon Lester

The Chicago Cubs keep making big moves in free agency with the addition of starting pitcher Jon Lester, who preferred joining them to playing for the Boston Red Sox, San Francisco Giants and the Los Angeles Dodgers.

Lester signed a six-year deal paying him $155 million, coming with a 7th year option that could take his total up to $170 million. Lester has spent almost his entire career with the Boston Red Sox, being part of two World Series campaigns (2007 and 2013) before being traded to the Oakland A’s last season. He was close to returning to Boston this fall, but the Cubs offered a bit more money, and something else as well.

According to Joe Maddon, the Cubs’ new manager, Lester joined the Cubs because he sees in them not just a team that’s going to be contending for the playoffs, but also a team he can go to the World Series with sooner than anyone thinks. The Red Sox offered him $135 million on a six-year deal with no vesting option. Lester, who made his debut in Major League Baseball back in 2006, will be turning 31 next month. Lester also rejected a four-year, $70 million extension offer from the Red Sox last spring, knowing a good season was going to bring him a lot more.

Lester is 6-4 with a 2.57 ERA in postseason play, maybe the thing that makes him more valuable than anything else. He is 3-0 with an 0.43 ERA in three starts in the World Series, but the Cubs, despite their new signings, are still a very long way from going that far.

Lester has been constantly improving over the last three years, propelling himself to be one of Baseball’s elite pitchers, doing it in the American League. He had a 2.46 ERA in 2014 with a strikeout rate of 25%, a walking rate of 5.4% and keeping righty batting averages at .230.

The Cubs have had five consecutive losing seasons but their rebuilding is finally going in the right direction, having a seven-win bump from 2013 to 2014. They haven’t been in the playoff since 2008 and haven’t won a postseason series since 2003, the year one of their own fans possibly snatched away a possibility to play in the World Series.

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