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Red Sox, pitching market waiting on Jon Lester

The entirety of Major League Baseball seems to be waiting on Jon Lester to pick a team. Once he does, though, the Red Sox may find themselves up against a wall as the floodgates open.

Bob DeChiara-USA TODAY Sports

While the Red Sox moved quickly to snatch up two of the biggest free agents on the market in Hanley Ramirez and Pablo Sandoval, we're now better than a month into the offseason and they have yet to address their needs in the rotation. In fact, so far nobody in baseball has done that. The pitching market is at a complete standstill, and right now it seems as though that's because of Jon Lester.

While Lester will apparently not be making his decision by the week's end,  his market has certainly been the most active early on. At least six different teams have been actively "in" on the star lefty so far, and it seems like just about every other pitcher on the market and every other team looking to acquire them are waiting for Lester to sign.

This could be because Jon Lester represents the potential for a healthy middle ground between the madness that will be Max Scherzer, and the more reasonable but less-exciting James Shields. Scherzer is looking to Lester to give him a foundation to base his (higher) demands, while Shields is hoping that a big payday for Lester will push teams scared out of Scherzer's market into his, bringing him up towards the lefty's level, if he'll never quite reach it.

The big teams, on the otherhand, want to know whether or not they'll be able to play in Scherzer's market, or be forced into other options. Meanwhile, those that already have pitching and are looking to trade it--the Mets, Phillies, and Athletics of he world--have no reason to act before those who missed out on Lester are appropriately desperate for a solution that's at once better than James Shields and less expensive than Scherzer.

But once Lester is out of the way...Buster Olney, speaking on WEEI's Hot Stove Show, gives us an idea of the aftermath:

Whenever Lester does sign, Olney expects a flurry of moves involving a starting pitching market that has yet to start moving. Free agents could come off the board quickly, and trade activity could be significant.

"[Lester is] the biggest domino. He's the bottleneck in the whole marketplace right now," said Olney. "I will tell you that talking with some teams today and this evening, they're telling me that there's a ton of talk going on. Whereas three days ago there were a lot of teams that were just inclined to wait until the Lester thing happened, I think the fact that it may not get resolved to the middle of the winter meetings - which is the latest timetable I heard - I think teams are now lining up to do other things."

It sounds like the market will still wait for the Lester decision before any triggers are actually pulled, but with the meetings so close at hand, organizations have been readying their contingency plans. That means once Lester goes, there might not be much time at all before the best options are all gone, perhaps excluding special cases like Max Scherzer.

If the Red Sox end up being the ones to actually land Lester, that's all well and good. They could very well use a second pitcher, but shouldn't have too much trouble putting the finishing touches on the team with the biggest piece in Lester locked up.

If, on the other hand, it's the Dodgers or Cubs that come away with Lester, the Red Sox could be in trouble. It stands to reason that, if other teams are lining up their contingencies, the Red Sox are too. But their needs with Lester and their needs without are so dramatically different that they have to be spread thin. And if indeed this comes down to a frenzy of activity in the week to come, even the promise of Boston's substantial warchest might not persuade agents to keep their clients on a market that could rapidly fall out from beneath them as buyers and sellers match up.

The Red Sox could certainly come away from this just fine even if Lester winds up on another team, however much fans of his may feel otherwise. And even if they do bring him back to Fenway, the Red Sox will not be able to rest on their laurels if, indeed, they intend to add another pitcher before all is said and done. But it's hard to imagine a fast-paced market is good news for the teams that need to be most active. Just another reminder of why it's so important for Boston to get their man, particularly if they want to avoid being pressed into a Max Scherzer market that seems best avoided.