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12/05/07 10:47 PM ET

Santana negotiations proving arduous

Obstacles include satisfactory offers, ace's no-trade clause

NASHVILLE, Tenn. -- Trying to solicit a trade for the top left-handed pitcher in the game would, in theory, seem like an easy task.

The assumption is that teams would be knocking down the door of a club which is offering up a two-time Cy Young Award winner who turns 29 in March. However, ask Twins first-year general manager Bill Smith and his answer almost certainly would be that it's not as simple as it sounds.

It was the expectation around baseball that ace Johan Santana would be dealt during this year's Winter Meetings. Yet, after three days of speculation surrounding Santana's future, the Twins still had yet to come close to finalizing a deal for the ace southpaw.

"I don't know if I feel bad for Billy Smith, or if I feel good for Billy Smith," Blue Jays GM J.P. Ricciardi said Wednesday night. "He's in a tough spot."

The Twins certainly have received offers for Santana, but it's apparent that none have satisfied the team's wishes just yet. The Yankees included Phil Hughes, Melky Cabrera, and another prospect in their offer. In Boston's case, the Red Sox have put forth two packages -- one headlined by pitcher Jon Lester and another featuring outfielder Jacoby Ellsbury.

So, as the clock ticks along with just one day remaining at these meetings, it seems increasingly likely that the Twins will leave Nashville with Santana still on their roster.

Santana's agent, Peter Greenberg, spoke to a small group of reporters in the lobby of the Gaylord Opryland Resort & Convention Center on Wednesday and expressed his surprise by the current situation.

"I thought it would have been done already," Greenberg said of a trade involving Santana. "I think everybody did. I guess Bill hasn't gotten what he feels is fair value."

With Miguel Cabrera off the market following his trade to Detroit, the expectation was that more potential suitors could emerge for Santana. Smith acknowledged that some of the teams involved in the Cabrera chase might have to shift their focuses.

"I think teams that were in on Cabrera, who didn't get him, now have to look at what their alternative plans are," Smith said.

Many pundits felt that meant more teams rejoining the Santana hunt. That wasn't exactly the case on Wednesday.

Among the teams pursuing Cabrera were the Dodgers and the Angels. So far, neither of those teams has jumped back into the mix for the Twins ace.

A source close to the Dodgers said that Los Angeles might have some of the best matches for such a trade, but it's not giving up its prospects, which concerns the team.

What is stalling teams like the Dodgers from joining the hunt is the large contract extension a team will likely have to offer Santana to entice him to waive his no-trade clause. It's expected that Santana will receive an extension worth upwards of six years and $150 million from the team which obtains him in a trade.

Hot Stove

In the past, teams wanted to lock up players for a significant period of time. But considering the way the market is today and the risk of injury, a six-year extension -- which is what Santana is reportedly seeking -- seems more fearsome than obtaining a pitcher for just two or three seasons.

The list of teams that could afford to give up the number of prospects and pay off such a deal are limited -- mostly to the big markets. It's part of the reason why the only two teams currently linked to negotiations with the Twins are the Red Sox and the Mets.

"There's only certain teams who can be involved with trying to get that guy," Ricciardi said.

Boston is still considered to be the front-runner, even if there was a feeling by some early Wednesday morning that the interest of the Red Sox in such a deal had cooled.

"I can't address the Twins directly," said Theo Epstein, the Red Sox GM. "We certainly respect the position the Twins are in. We've had amicable dialogue throughout. I don't think either side has had any issue with the process whatsoever. We're going to be open-minded to continue in dialogue. At this point, we don't have a deal to announce. We're going to keep an open mind going forward and continue to try to improve the club."

Along with Boston keeping open talks with Minnesota, Mets manager Willie Randolph confirmed that his team is still in the hunt for Santana.

After pulling out of the race Monday, the Yankees have yet to throw their hat back in the ring -- although the feeling is that the club could always be a late addition to the talks. The Rangers have shown moderate interest in Santana, but it doesn't appear to be a match. The Mariners have also been rumored to have contacted the Twins again about Santana, but sources with ties to Seattle denied those reports.

With Santana still expected to be with the Twins when the meetings come to a close on Thursday, Smith was asked if he feels his team still has a chance to re-sign Santana to an extension.

"I said all along it's our first choice," Smith said. "We'd love to keep him."

That option still seems to be far-fetched considering the length of contract that Santana is seeking and the price tag that comes along with it. The general consensus at these meetings is that Santana will not start the year in Minnesota and that a trade will indeed take place sometime before Spring Training.

But if the Twins do have to wait until the start of the season to get the offer they are looking for, they aren't the worse for it.

"Bill knows what he wants to do," Ricciardi said. "If they keep him, they have a pretty good player."

Kelly Thesier is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.