Playing Santana all night long

Tim Brown
Yahoo Sports

NASHVILLE, Tenn. – Monday evening became Tuesday morning, well past The Steinbrenner Deadline, or the moment the Minnesota Twins supposedly would no longer be allowed to unload the best left-hander in baseball on the New York Yankees, and baseball’s winter meetings began to skew even more toward pitching.

In fact, an hour past midnight in New York and right around midnight at the Opryland Hotel, it was the Boston Red Sox who appeared closest to a deal with the Twins for Santana.

Late Monday night, according to a Red Sox source, the team handed over medical records for left-hand pitcher Jon Lester, the critical piece in a four-for-one trade that would bring Santana for Lester, Coco Crisp, minor-league right-hander Justin Masterson and another minor leaguer. Lester returned to the big leagues in late July after recovering from lymphoma, and was the winning pitcher in Game 4 of the World Series, the clincher for the Red Sox.

A Red Sox official said he was "cautiously optimistic" the club could complete the deal for Santana, putting the two-time Cy Young Award winner next to Josh Beckett, Curt Schilling, Daisuke Matsuzaka and, probably, Clay Buchholz in the Red Sox rotation.

The Red Sox, however, were leery of a late play by the Yankees, along with a robust market for Santana. The Seattle Mariners, among other teams, had contemplated swooping in when The Steinbrenner Deadline passed.

Apparently, this particular bit of Yankees business will be different from other recent examples of pinstriped rigidity, such as The A-Rod Decree, which stipulated Alex Rodriguez would never, ever be welcome at the negotiating table … unless he took their $300 million, and The Posada Principle, in which the Yankees would not go longer than two years on a contract for catcher Jorge Posada, and certainly no longer than three years, until it got to four.

Regardless, Monday slipped past midnight, and Santana remained the property of the Twins, and the Yankees had not parted with a trio of players said to include right-hander Phil Hughes and center fielder Melky Cabrera, and the question bubbled: Seriously, would the Yankees accept a trade for Santana over margaritas Monday night but not over bagels and cream cheese Tuesday morning?

At the same time, the Boston Red Sox were sensing they were back in the game for Santana.

While the winter meetings and its 30 participants hardly froze at the nearing of The Hank Ultimatum – the new Steinbrenner boss's decree that the Yankees would end negotiations with the Twins at the stroke of midnight – there remained a sense the whole affair Santana (as it related to the Yankees) would have to be resolved before we’d really know how serious the Oakland A's were about trading Dan Haren and/or Joe Blanton, the Baltimore Orioles were about trading Erik Bedard, and the Milwaukee Brewers, possibly, were about trading Ben Sheets.

The Twins, meanwhile, appeared to treat the Yankees deadline with something between irritation and bemusement, while continuing to shop Santana to the likes of the Red Sox, Mariners, New York Mets, Los Angeles Dodgers and, perhaps, the Detroit Tigers and Arizona Diamondbacks.

The Red Sox and Yankees remained Santana's most likely destination into the evening, because they have just enough disposable prospects to get him and all of the disposable income to carry the resulting contract extension.

In the middle of all that came word Andy Pettitte was probably not going to retire, that he'd rejoin the Yankees' rotation, which was a huge relief to the Yankees but had little bearing on the Santana negotiations. The Pettitte presence means the Yankees have two relatively sure things in their rotation – Wang and Pettitte – along with Mike Mussina and two of Joba Chamberlain, Ian Kennedy and Hughes. Pitchers develop at different rates, and September doesn't always translate into April through August, and so the Santana discussions continued.

The sense coming into the meetings was that Billy Beane would hold Haren and Blanton for the Santana losers, but Beane appeared to be getting plenty of play on them on day one. The Tigers were believed to be willing to part with Andrew Miller as part of a package for Haren, and the Diamondbacks were believed to be in on both A's pitchers. The Mets need to add at least one top-end starter (and probably have enough in prospects to land just one) and appear to be focused more on Bedard, though that could change in a phone call.

General managers are wandering through the labyrinth-like Opryland hotel muttering about the high cost of pitching, so you know at least half had talked to the Twins, A's or Orioles.

The Los Angeles Angels can line up as many as seven starters (depending on how one feels about Ervin Santana these days) and so are fielding a lot of calls about the perceived depth in their rotation. It was once believed they acquired Jon Garland to cover themselves when they went to acquire Miguel Cabrera from the Florida Marlins – in fact, that's what they believed – but might end up using all the depth to cover for Kelvim Escobar, whose ERA was more than seven in September, and Santana.

The Angels have at least a couple times assumed they were very near to having Cabrera at third base and behind Vladimir Guerrero in the lineup, but there are none in the organization who assume that now. In fact, the go-go Angels front office is thinking more in terms of Miguel Tejada at third base (or shortstop) than Cabrera, which potentially could flower into something larger. The Orioles could lash Tejada to Bedard in a larger trade, presumably in exchange for that pitching depth in Anaheim.

"There are teams that have called just because the perception out there is we are pretty deep both in the outfield and pitching-wise," Angels general manager Tony Reagins said.

Asked what he thought of that perception, Reagins nodded and said, "I think it’s accurate."

For a time, the San Francisco Giants resigned themselves to the reality it would take Tim Lincecum or Matt Cain to upgrade their offense, but GM Brian Sabean told Bay Area writers that he's leaning toward taking those top-end young pitchers out of all discussions and convincing himself the Giants could pitch well enough to compete.

So, the rush of trades that was to drive these winter meetings and rework the rotations at the tops of divisions all over the game was delayed at least a day. Elijah Dukes went to the Washington Nationals. Carlos Quentin went to the Chicago White Sox. The St. Louis Cardinals shopped for a leadoff hitter (Coco Crisp, perhaps), a Los Angeles Dodgers contingent arrived looking for pitching, third base and outfield help, and the Chicago Cubs hoped to add an outfielder.

But, what everyone was thinking about was Santana.

And the Yankees. And the Red Sox. And the clock.