People involved in the talks said they believed the situation was coming to a head and that Minnesota would soon decide between the Yankees and the Red Sox offers. New York has been seen as the favorite, but Boston may have jumped back into the mix given the midnight phone call.
The Twins and Yankees reached what one person called an "impasse'' shortly before midnight CST. The Twins were asking that the Yankees include either pitcher Ian Kennedy or a tandem of pitching prospect Alan Horne and outfield prospect Austin Jackson in their package with pitcher Phil Hughes and outfielder Melky Cabrera.
The Red Sox have made offers that included Lester or outfielder Jacoby Ellsbury, but not both players. Boston also has been willing to include other top prospects, such as pitchers Justin Masterson or Michael Bowden and shortstop Jed Lowrie.
The Yankees told the Twins earlier that they did not want to trade either Horne or Jackson, and certainly not both. Two general managers from other teams described Horne as "a No. 5 starter,'' but one scout said Jackson has tremendous potential.
The midnight deadline set by Yankees owner Hank Steinbrenner -- whether he meant EST or CST -- passed without a deal. The Twins, however, reportedly felt more amused than threatened by New York's ultimatum and when no agreement was reached early Tuesday, they simply resumed talking to the Red Sox.
"It's still something that we can't do," Steinbrenner told the Associated Press on Tuesday morning . "As far as I'm concerned, it's probably off."
While refusing to discuss Santana specifically, Red Sox general manager Theo Epstein said he had no expiration date on any trade talks. In the past, he has set a deadline for potential deals if they were holding up other deals.
"I think we've only done that when we thought it was in our best interest," Epstein said. "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."
Other trades were percolating in the meeting rooms.
Florida is expected to deal third baseman Miguel Cabrera sometime soon, and Baltimore is shopping shortstop Miguel Tejada. Oakland is checking out the market for pitcher Dan Haren.
Yankees general manager Brian Cashman admitted there's a fear that players he might trade could win Cy Young Awards for another team.
"I'm definitely fully invested in a lot of the young talent. You get attached to it," Cashman said.