With the Yankees' offer now upgraded to include top young pitcher Phil Hughes, the Twins spoke again with the Red Sox late Saturday afternoon, sources say, and Boston generated a few new ideas for its proposed offer.
The Twins have also been talking with the Mariners and Dodgers, among other teams, but with Santana in a position to steer the deal making with his no-trade clause, Minnesota may soon have to decide between the offer from the Yankees and Red Sox or consider the possibility of keeping Santana for the outset of the 2008 season -- although executives involved in these talks expect Santana to be traded.
There is only a certain level of patience for prolonged dialogue among the teams involved, and unless some preliminary trade agreement is settled, the Red Sox or Yankees could reduce their offer or pull out altogether within the next 48 hours.
If the Twins make a deal with New York, Yankees officials are confident they will sign Santana. And the club's internal plan, if center fielder Melky Cabrera is included in the trade, is to switch veteran Johnny Damon from left field back to center field.
Boston's offer on the table before Saturday's talks included pitcher Jon Lester, center fielder Coco Crisp and minor league infielder Jed Lowrie. A fourth player -- a minor league pitcher -- is to be determined. The Twins have wanted the Red Sox to add either Ellsbury or Buchholz to the deal, and there are indications that if the Red Sox add Buchholz or Ellsbury, theirs is the offer that Minnesota would prefer.
For now, however, the Yankees are right in the thick of the bidding, having decided in internal discussions on Friday to offer Hughes rather than Ian Kennedy into their offer, along with Cabrera and a third player -- in all likelihood, a minor leaguer. The Yankees have told the Twins that the third player can't be any of their best young players -- Kennedy or Joba Chamberlain or second baseman Robinson Cano, for example, but a second-tier prospect.
Santana, 29, has a full no-trade clause, and could block any deal the Twins try to make. In return for waiving the no-trade clause, it's expected that Santana will want the Yankees or any other team attempting to trade for him to sign the left-hander to a record-setting contract. No pitcher has ever signed a multiyear deal for more $18.6 million per season, but Santana may ask for something in the range of six years and $150 million, in an extension.
The Yankees are operating under revamped leadership, with Steinbrenner sons Hank and Hal assuming a greater role, and to date, the sons have demonstrated a willingness to bid aggressively and splurge when they feel it's necessary to get a deal done.
For example: While the Yankees forced Alex Rodriguez to come to them without Scott Boras, they still gave him a record-setting raise. Many industry executives think the Yankees were in position to force Rodriguez to settle for a deal in the range of $200 million-$225 million, but the Yankees signed Rodriguez to a deal that could be worth anywhere from $275 million to $305 million. And the Yankees gave veteran catcher Jorge Posada a fourth year in their offer, rather than limit their proposal to three years.
Damon, 34, battled injuries in the early part of last season and in his absence, Cabrera played center and so greatly improved the team's defense that when Damon was ready to return to the outfield again, Cabrera remained as the center fielder, with Damon moving to left.
As the Yankees have considered the alternatives in a Santana trade, they've determined to shift Damon back to center field, rather than to pursue one of the many free agent center fielders available -- someone like Aaron Rowand, Mike Cameron or Andruw Jones.
There is more pressure on the Yankees to acquire Santana or another veteran pitcher, because the projected Yankees' rotation, as of today, lacks experience, and because friends of left-hander Andy Pettitte believe there is a real chance that he is going to retire. The Yankees may not learn until late December or January about what Pettitte's plans are for 2008.
Those considerations may nudge the Yankees into adding Hughes to their offer for Santana.
The Yankees and Red Sox are also engaged in ongoing talks with the Oakland Athletics about Dan Haren, an accomplished pitcher who is a much cheaper option than Santana. Haren would cost, in prospects, a package comparable to what Santana is commanding, but he is already under contract for the next three years at $16.25 million (presuming his team exercises an option for 2010).
Buster Olney is a senior writer for ESPN The Magazine.