After Yanks' deadline passes, Red Sox jump into lead for Santana

Updated: December 4, 2007, 10:07 PM ET
By Jayson Stark | ESPN.com

NASHVILLE, Tenn. -- While Hank Steinbrenner set deadlines and publicly lusted after Johan Santana, the Red Sox just bided their time and stayed in the game.

And what do you know? As Monday night turned into Tuesday morning at the winter meetings, suddenly it was the Red Sox who loomed as the favorites to pull off a deal for the best pitcher in baseball.

ESPN the Magazine's Buster Olney reported early Tuesday that the Twins asked the Red Sox for permission to review the medical records of pitcher Jon Lester, amid indications a Red Sox-Twins trade could go down sometime during the early-morning hours. As of Tuesday evening, however, no deal had been completed.

"I know there's a lot of speculation that we're close to something big," Red Sox general manager Theo Epstein said on Tuesday evening, according to The Associated Press. "Until we reach an agreement, then we're not that close."

If the Twins were satisfied with Lester's medicals, it was believed they would accept a swap of him, Coco Crisp, shortstop prospect Jed Lowrie and either highly regarded pitching prospect Justin Masterson or another player.

Jon Lester

Lester

Johan Santana

Santana

Or if the Twins reversed field and decided they wanted center fielder Jacoby Ellsbury instead, it's believed that would be a 3-for-1 trade -- with only Ellsbury, Masterson and Lowrie going to Minnesota.

However, the Red Sox apparently remained adamant that while either Ellsbury or Lester was available, they would trade one or the other -- but not both.

If the teams agree to the players, the Red Sox would try to work out a contract extension with Santana, a 28-year-old lefty who is eligible for free agency after the 2008 season.

"We have no payroll constraints. Our issues aren't payroll right now," Twins general manager Bill Smith said. "Some of it is more length. Length of contract is an issue. Some things around groundbreaking issues. I'd just as soon leave it at that."

The Twins also spent much of Monday night exploring potential 3-for-1 and 4-for-1 trades with the Yankees -- and getting shot down on all their proposals.

According to baseball officials who were aware of those talks, the Twins initially asked for pitcher Ian Kennedy, along with right-hander Phil Hughes and outfielder Melky Cabrera.

After being told Kennedy wasn't available if Hughes was part of the deal, the Twins apparently proposed expanding the trade into a 4-for-1 swap, with players they considered to be lesser prospects than Kennedy. But the Yankees quickly rejected that pitch, too.

That last proposal included Hughes, Cabrera, pitcher Jeff Marquez and either pitcher Alan Horne or outfielder Austin Jackson.

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All this took place while the Yankees counted down toward their self-imposed Monday night deadline, set by senior vice president Hank Steinbrenner, who said the Yankees had the best deal on the table and threatened to walk away if the Twins didn't say yes.

"A deadline is a deadline. It was pretty much done as of this morning," Steinbrenner said on Tuesday, according to AP. "He's a fine pitcher, but there's a lot of things that go into this. This isn't fantasy baseball."

AP reported that the Twins finally dropped their demand that Kennedy be included, but the sides couldn't agree on a third player.

"For a while, there's no question, they asked for too much," Steinbrenner said on Tuesday, according to AP. "To tell you the truth, toward the end, Minnesota negotiated in good faith. They really did. I have no problem with them. It was something we just couldn't do."

Smith wouldn't discuss the talks specifically on Tuesday. He also refused to get into whether he was upset with Steinbrenner's repeated public comments about negotiations. When asked about Steinbrenner, Smith responded with praise for Yankees general manager Brian Cashman.

"I have the greatest respect for Brian Cashman. He's a gentleman. He's a classy professional in this game," Smith said, according to AP. "I don't have any problems with the Yankees. They've been good to the Twins. They've been good to the Twins for a lot of years."

The deadline was intended to nudge the Twins into action. Little did the Yankees suspect it might actually work to the Red Sox's benefit.

Smith sounded in no rush to make a deal.

"Johan Santana is a consummate professional. He's a great, great representative of this organization," the GM said. "But in all scenarios, we're going to try to make good baseball deals. We're going to try to make good decisions that benefit this club. And, as I say, if Johan is our opening-day starter, that's not bad."

All along, the Yankees seemed to believe that the Red Sox weren't seriously pursuing Santana, that the Boston game plan was to stay just interested enough to force the Yankees to overpay for him. Apparently not.

One source who spoke with the Red Sox delegation told ESPN.com that the Red Sox group was just sitting around its suite Monday night, watching the Patriots-Ravens game, when Smith called and asked to see Lester's medicals.

That got those teams' wheels turning again -- and did so, coincidentally, at the same time the Yankees were almost simultaneously beginning to talk themselves out of this trade.

Officials from other clubs said several of the Yankees' baseball personnel at the meetings had begun openly questioning whether they even wanted to make this trade if the Twins said yes.

The Twins haven't budged since Friday. They wanted Kennedy then, and they still did on Monday.

Meanwhile, officials from other clubs said some Yankees baseball personnel at the meetings have continued to agonize over the inclusion of Hughes in their offer, out of fear Hughes could come back to haunt them for years. So clearly, the decision to include Hughes in the first place was far from unanimous.

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, according to the AP.

And if the Yankees had any inclination whatsoever to waver on their stand a few days ago, the news Monday that Andy Pettitte had decided to return undoubtedly helped ease those concerns.

With Pettitte back, the Yankees can mount a respectable rotation, with or without Santana -- around Pettitte, Chien-Ming Wang, Hughes, Chamberlain, Kennedy and Mike Mussina. They also are expected to renew their efforts to trade for Oakland's Dan Haren.

But if the Red Sox wind up sweeping Santana out from under them -- and adding him to a rotation that already includes Josh Beckett, Curt Schilling and Daisuke Matsuzaka -- it will be fascinating to see if the Yankees feel the need to respond by reeling in another ace of their own.

"If the Red Sox get Santana," said an executive of one NL team that's grateful to be in the other league, "they might be the best team in the history of the frigging universe."

Schilling agreed.

"A rotation featuring Beckett, Santana as the top two is pretty much as good as it can get. The thought of pitching behind these guys has to fire ya up," Schilling wrote on his blog, 38pitches.com on Tuesday. "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."

Also Tuesday, agent Scott Boras said he has added Ellsbury as a client. Ellsbury had previously been represented by Joe Urbon.

In other news, Boston's David Ortiz was honored for the fifth consecutive season as designated hitter of the year. Ortiz batted .338 with 33 homers and 113 RBIs as a DH in 2007, adding a .629 slugging percentage and 51 doubles.

Jim Thome of the Chicago White Sox was second, and tied for third were Toronto's Frank Thomas and Cleveland's Travis Hafner.

The trophy is named for longtime Seattle Mariners DH Edgar Martinez, who was honored five times before he retired in 2004. Ortiz is the only other player to win five times, and the only one to win it five years in a row.

Jayson Stark is a senior writer for ESPN.com. His new book, "The Stark Truth: The Most Overrated and Underrated Players in Baseball History," has been published by Triumph Books and now is available in bookstores. Click here to order a copy. The Associated Press contributed to this report.

Jayson Stark | email

Senior Writer, ESPN.com

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