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Jon Lester agrees to sign with Chicago Cubs

The race is over, and the Red Sox have lost

Jeff Curry-USA TODAY Sports

The Jon Lester race has come to an end, and the Red Sox have lost, as their long-time ace agreed to sign with the Chicago Cubs on a six-year, $155 million contract in the early hours of Wednesday morning. Ken Rosenthal had the news first.

In the end, it seems to have come down to money, at least when it came to the final choice between the Cubs and Red Sox. Jon Lester, true to his word, did not go to the highest bidder, as the Giants apparently offered a seven-year deal at $168 million, and the Dodgers were rumored to have gone even higher. But when torn between two teams where his personal connections ran deep--Boston, which had been his second home for the last eight years, and Chicago, led by the front office that had backed him in his trip through the minors and battle with cancer--Lester ultimately went with Chicago's $155 million offer, well north of Boston's final landing spot of $135 million.

For the Red Sox, the offseason suddenly becomes precarious. They have already invested nearly $200 million in signing Pablo Sandoval and Hanley Ramirez, meaning there can be no question of going into the season with a rotation full of holes. This isn't simply about finding the right number of bodies to start 162 games--the Sox are essentially priced into making quality additions to avoid having their other investments undermined by one glaring weak spot.

That leaves them in a very difficult spot indeed. Jon Lester was seemingly the ideal solution. A player they knew, and one they trusted, who could be had for money alone, was of the appropriate quality, and if expensive, was not going to break the bank in the ways Max Scherzer aspires to. Now they're left with few options who match Lester's quality, none of them coming in at Lester's price point. It's hard to imagine a desperate Sox team going to the necessary lengths to sign Scherzer, but trading away the future in a reactionary move for Cole Hamels? Overpaying for the distant third place in this year's market in James Shields? The offseason is suddenly full of landmines, and the Red Sox have precious little time to navigate it before their options start drying up.

And, underneath it all, there's the simple fact that Jon Lester has very likely pitched his last game in a Red Sox uniform. The longest-tenured pitcher on staff, the lefty whose presence has anchored this rotation from the first days of Josh Beckett's decline to the 2013 World Series and beyond is gone for good. What's even stranger is that he hasn't even been here since July. The wound feels fresh, but it's already five months old.

Perhaps in a few years we'll have our next Jon Lester up from the minor leagues, and that wound will start to heal. For now, though, there's a hole in Boston that even another ace won't quite be able to fill.