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Cubs pay Lester record-setting sum for chance to win now

Charles Krupa/Pool Photo via USA TODAY Sports

These aren't your father's Chicago Cubs – or grandfather's, for that matter. In fact, the Cubs are hoping not even a membership to an online ancestry portal will help you recognize the latest iteration of one of baseball's most storied franchises.

Jon Lester is a Cub. So is Miguel Montero, Jason Hammel and Joe Maddon. They join a group that already includes Anthony Rizzo, Starlin Castro and just about every high-end prospect you've been hearing about for the last several years. 

It's a team with significant holes but deeper pockets. Five straight last-place finishes, but a championship-winning front office hell-bent on changing a losing culture.

Cubs president Theo Epstein and his staff are betting a franchise-record contract that Lester will help restore relevance to Wrigley Field. They're gambling $155 million on buying out over 100 years of losing.

Lester's signing is Chicago's most significant move since introducing Maddon as its new manager last month and reunites the lefty with Jed Hoyer and former Boston Red Sox GM Epstein, who won a ring with the pitcher in 2007.

Following the club's acquisition of Maddon, much has been made about its efforts – and timeline – to build a contender. By acquiring one of the top lefties in the game, the Cubs have made clear their intention is to win now.

Lester, 30, posted career bests in ERA, WHIP and innings pitched across 32 starts with the Red Sox and Oakland Athletics in 2014. He was particularly effective over the final two months of the season with Oakland, recording a quality start in all 11 outings after the trade.

(RelatedRed Sox's $135 million offer to Lester falls short)

Lester's recent three-year WAR average of 4.5 justifies his $25.8-million yearly salary – second to Los Angeles Dodgers ace Clayton Kershaw – at least for the next few seasons. And although the aging curve for starting pitchers isn't all too flattering, the Cubs can afford to absorb such a decline in production.

For now, though, the Cubs rotation just received a major upgrade, acquiring one of the premier left-handers in the game and filling the No. 1 spot in a staff that desperately lacked an ace. 

Lester's presence every fifth day further bolsters a team loaded with top young talent and promises to serve as the catalyst for a domino of anticipated moves. They now boast a strong catching tandem, are well-positioned up the middle and offer plenty of future power potential at the corners.

The Cubs need to add an arm or two to supplement a staff that also includes Hammel and breakout arm Jake Arrieta, especially if they intend on competing this year. With Javier Baez, Jorge Soler (pictured above), and Kris Bryant likely in need of additional seasoning, the Cubs still look to be a couple pieces away from playoff contention.

But the Cubs didn't make Lester the second highest-paid pitcher in baseball for a shot at the title in 2019. They didn't bring in Maddon to mentor a roster of young-ins content to settle for moral victories and incremental growth. 

The Cubs paid a pretty price for the chance to win now and, after a century of losing, can you really blame them?

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