Where will Jon Lester sign?

SAN DIEGO -- Once upon a time, Jon Lester hoped he'd have his next team all picked out before the winter meetings. So much for that.

Then he hoped he could get this saga wrapped up in the first day or two of the winter meetings. Now that's not looking so promising, either.

As the sun set Monday evening over Mission Beach, Lester and his agents, Seth and Sam Levinson, were still sorting through their options. Although there were indications a decision might be nearing on Tuesday, there were no promises this soap opera wouldn't drag into Wednesday -- or maybe even beyond.

Meanwhile, four teams wait nervously for Lester's momentous decision. Or maybe five teams, if you want to believe rumblings of the Yankees hovering, or six, if you buy that the Angels want to move C.J. Wilson's contract to make a run at Lester.

But we'll leave the Yankees and Angels out of it for now and ask: Where do those four teams stand? It's the biggest question of the winter meetings. So let's take a look, with the proviso that this story changes by the minute -- so keep that in mind!

CUBS (ODDS: 3-to-1)

What a great position for this team to be in. If Theo Epstein, Jed Hoyer and Joe Maddon reel in Jon Lester, they're essentially announcing to the world, "We're all in. We're going to win. We're going to be a force. And it starts right now."

And if they don't get Jon Lester? Then what the heck? They weren't ready to win anyway. Not really.

They can poke around on a Cole Hamels deal or a Jordan Zimmermann trade. But they can also kick back and wait until next year, when Kris Bryant will be mashing in the big leagues, Javier Baez and Jorge Soler will have another year's mileage on their radials, and the next free-agent market will be overflowing with the likes of Zimmermann, David Price, Zack Greinke and even Jeff Samardzija. Then they can do this all over again with one of those studs.


Except the Cubs haven't chased Lester like a team with nothing to lose. They've chased him like a team that wants him and needs him and just might do whatever it takes. Maybe even a contract north of $150 million, which would be the largest largest free-agent deal in history. More and more, at least to the lobby crowd, they're beginning to feel like The Team.

GIANTS (ODDS: 5-to-1)

In the beginning, for whatever reason, not many people thought the Giants were a serious bidder in this derby -- or, to put it another way, a serious threat to actually win this derby.

That's not true anymore. Practically the first thing the Giants delegation did after they checked into the Manchester Grand Hyatt on Sunday, aside from maybe brushing their teeth, was meeting with Lester's agents and making a monster push to sign him.

Friends of Lester report he was blown away by their meeting with him last month, by what he observed during his time in Oakland and everything he's heard since. So why, if the team feels right and the fit feels right and the offer, from all indications, was in the neighborhood he was looking for, hasn't he chosen the Giants?

That's what they'd like to know, too. An exec of one club that spoke with the Giants brass says they're still optimistic but are concerned Lester is waiting for something else to happen in these negotiations -- another team, another offer, etc. They've received assurances that's not the case, but you can't blame them for sweating this one out.

RED SOX (ODDS: 8-to-1)

Red Sox manager John Farrell marched into the interview room Monday and said of Lester, "We're still confident we can sign Jon." But can they? Really?

The price tag has now soared to more than twice the four years, $70 million the Red Sox offered him in spring training. Although the Red Sox have tried to make a case that they were always willing, even then, to go well beyond that offer had negotiations progressed, it gets more confusing all the time to see them pushing into the outer limits of a whole new financial orbit to sign that same player they'd once low-balled.

"I don't see how the Red Sox get this done," said an official of one club who has been monitoring these negotiations closely.

The truth, though, is no one except Lester and his agents really know if that's accurate. We know they keep meeting with him. So whatever scars those negotiations last spring left on him, they clearly weren't painful enough for him to tell them to get lost this time around.

But Lester's friends don't get the impression he's going back there. Maybe they're right. Maybe they've been reading the wrong tea leaves. But as we keep mentioning, only Jon Lester (and his agents) know for sure.


It was only a few days ago the Dodgers were the unnamed mystery team in these negotiations. Remember? But now, even though they've been named, they're still just as big a mystery as the Loch Ness Monster.

They haven't tipped their hand to anyone, so this is all uneducated speculation. Are they just in this to bid up the price tag until the Giants throw in their cards? Are they just in this because they're in on everything and anything?

Or are they looking over the horizon at the prospect of Greinke opting out of his contract next winter and scooping up his replacement because it's too tempting not to?

Maybe their owners, who apparently have bags stuffed with money sitting on every desk, just decided they couldn't take a chance on this guy becoming a Giant and ordered their man, Andrew Friedman, to keep dumping dollar bills in front of Lester until he says yes.

Both publicly and privately, the Dodgers have been as tight-lipped on this topic as they have been on just about anything since the Guggenheim fortune entered their world. So we can only guess what they're up to. And so, for that matter, can the other teams in this hunt.

As darkness fell on the scenic San Diego waterfront Monday night, Jon Lester was still the talk of the winter meetings. Will that talk last through another day? Two more days? Even longer? That answer seems to change every minute. So our advice is: Don't let the Jon Lester suspense kill you. It's just getting fun.