For most of these negotiations, the Red Sox have been willing to offer either Lester or center fielder Jacoby Ellsbury -- in addition to shortstop prospect Jed Lowrie for Santana. If the Twins wound up taking Lester, the Red Sox could well put center fielder Coco Crisp in the deal. The Twins, after losing Torii Hunter via free agency, need a center fielder.
ESPN.com reported early Tuesday morning that the Red Sox have emerged as the "favorite" to land Santana.
When the day started, it seemed that the Yankees had held that distinction. Yankees senior vice president Hank Steinbrenner imposed a deadline of the end of Monday to get a deal done, and it passed with no deal in place. But there's no telling if talks might yet resuscitate between the Yankees and Twins.
There was also the chance the Twins could simply hang on to Santana for another season.
While Steinbrenner had no problem professing his club's interest in Santana, Red Sox general manager Theo Epstein won't even mention the left-hander by name.
"I don't want to talk about other teams' players," said Epstein, who is ever mindful of making sure he will never be accused of tampering.
Epstein didn't seem inclined to take a page out of Steinbrenner's book and impose a deadline on the Twins.
"I think we've only [set deadlines] when we thought it was in our best interest," Epstein said Monday night. "We don't have current discussions ongoing for which I think that would be in our best interest. We're pretty content with where we are and we don't think anything major is getting held up. There's a natural order of things this winter and we're just going to let it play out. If we think the dynamic changes or our interest changes, we certainly wouldn't hesitate to put a timetable on something or other, but this doesn't apply right now."
Before the Yankees and Red Sox held talks with the Twins Monday evening, Epstein didn't sound as if he was close to executing a trade -- blockbuster or otherwise.
"Obviously, we've made calls and talked to a couple of teams about deals and talked to a few agents, but we don't have anything to show for it," Epstein said. "That might be par for the course. It seems like everything is on a later schedule this year."
But perhaps there was a change in momentum by the end of the night.
If the Twins insist that Lester and Ellsbury both be in the deal, it's doubtful the sides will reach common ground. That could open up a chance for the Angels -- or maybe some other teams -- to swoop in. Or the Twins could always keep Santana.
In fact, agent Peter Greenberg, who represents Santana, strongly denied that the pitcher would only waive his no-trade clause to play for the Yankees or Red Sox.
"He was very adamant about that. He wanted to make sure we clarified that. That upset him," Greenberg told The Associated Press. "He's been very clear all along that he wants [Twins GM] Bill [Smith] to make the best deal possible."
Any team that agrees with Minnesota on a trade would likely have 72 hours to negotiate a contract extension with Santana, otherwise it is doubtful the lefty would waive his no-trade clause.
Aside from the Santana rumblings, the Red Sox are looking to make moves that are more complementary in nature. The World Series champions have their entire starting nine and pitching rotation under contract for 2008.
"Just for us, everything seems to be a little slower, probably because the holes on our club right now are really for reserve roles and that part of the market usually settles later," said Epstein. "Our phone is ringing probably less, with the exception of a few players who are perceived to be somewhat available. Our phone is certainly ringing less than it has in previous years. Some teams might look at our roster and say, 'They're set, they're not going to do anything.'"
Is Epstein investigating the availability of front-line pitchers?
"Yeah, but I wouldn't distinguish between pitchers and position players," Epstein said. "We certainly have an obligation to explore any potential opportunity that might make us better. That doesn't mean we're abandoning our core or abandoning our philosophy on how we're going to sustain success year in and year out. We see it as our job to explore every possible way to get better in the future."
Though Epstein is staying quiet publicly on all things Santana, it is big news in Boston.
Sox right-hander Curt Schilling even blogged on the matter on Monday.
"A rotation featuring Beckett, Santana as the top two is pretty much as good as it can get," Schilling wrote on 38pitches.com. "The thought of pitching behind these guys has to fire [you] up. That being said I look at it like this.
"If we make the move we'll have done so with Theo knowing whatever he had to trade to acquire him he can restock those spots either from within, or via trade. How much is too much when you're talking about trading for the best left-handed pitcher in the game? How much is too much when you consider what he and Josh could do over the next 5-6 years."
In dissecting the possibility of the trade, Schilling feels as if everything is in the hands of the Twins.
"I don't see any of the other players holding this deal up from either NY or Boston," Schilling wrote. "Neither team will let him slip through their hands because they want to hold onto a AA or AAA potential star. I think it's going to come down to the value Minnesota places in Philip Hughes/Melky Cabrera vs. the top 2-3 players in this deal from our side."
Among the visitors to the Winter Meetings on Monday was Twins closer Joe Nathan, who lives in Knoxville, Tenn.
"We'll see what happens," Nathan said. "It's obviously a situation where if Johan goes to Boston, that starting rotation is going to be pretty tough to beat."