It's time for the Boys of Winter

Dec 6 2009 - 10:18pm

In a perfect world, Omar Minaya will come home from the winter meetings with a power-hit ting left fielder and a No. 2 starter, just as Brian Cashman will find an insurance policy in case Andy Pettitte decides to retire. That's the script everyone loads up for Opening Day in a matter of 72 hours -- but don't count on a swap meet this week in Indianapolis.

Recent history suggests the meetings are more like an extended chess game between general managers, agents and non-tethered players. The talent pool is thinner this year than in the past, which figures to intensify the be hind-the-scenes maneuvering.

Here are some of the people to pay attention to this week and beyond:

MATT HOLLIDAY: It appears the Cardinals won't be able to hold on to the left fielder, having decided to keep the payroll to $100 million in 2010. Instead, the team is focusing on Albert Pujols, who becomes a free agent after 2011. Holliday might've initially wanted to remain team mates with Pujols, but his agent Scott Boras is looking for a deal worth $23 million, far beyond the Cardinals' reach.

The Mets would love to jump in, but the Red Sox, who prefer Holliday to Jason Bay, have the inside track. But they're smart enough not to show their hand to Boras too soon, lest he get the Yankees involved in a bidding war. Holliday won't get that $23 million, but the Sox will come close enough to make it tempting.

ROY HALLADAY: The Yankees are officially involved in the hunt for the Jays' ace, although that conflicts with the organization's hope to keep the payroll under $200 million next year.

Somehow, Cashman would like to snare Halladay without having to surrender Joba Chamberlain or Phil Hughes. If the Yankees stick to that condition, the Yankees run the risk of seeing Halladay traded to the Red Sox. They, too, have reservations about parting with young talent -- in this case, Clay Buchholz -- but GM Theo Epstein is well aware of what a Yankee- killer Halladay is.

According to the Elias Sports Bureau, Halladay's .750 winning percentage against the Yankees ranks third all time among pitch ers with at least 20 decisions against them. Overall, he's won more games than any pitcher in baseball since 2006 (69).

But how much is Halladay really worth, pitching most of next sea son at 33? Make no mistake, the Yankees love this guy, but they're aware of the risk in trading Hughes or Chamberlain and a prospect such as Austin Jackson or Jesus Montero. Halladay has thrown 710 1/3 innings over the past three seasons. The only pitcher who has more is CC Sabathia, who's totaled 779 1/3, including the postseason.

JOHN LACKEY: With Chone Figgins on the verge of signing with the Mariners, Lackey's return to the Angels seems more likely to happen. Put it this way: the right- hander is in a much better bargaining position with owner Arte Moreno, who is rightfully wary of the threat the Mariners could pose next year.

The Rangers loom as the next- best option for Lackey, with the Phillies close behind. The Yankees will monitor those talks, as well.

BRIAN CASHMAN: His initial order of business will be to elicit an answer from Pettitte about 2010 our strong hunch is that the left hander is indeed returning and then negotiate another one-year deal with a sizable raise over the $5.5 million Pettitte was guaranteed in 2009.

Cashman then will turn his gaze toward Johnny Damon and learn whether the left fielder will soften his insistence on a three or even four-year contract.

If not -- if Boras aggressively pushes Damon as the contractual equivalent of Jorge Posada -- the Yankees could be looking at Mike Cameron or Rick Ankiel as free- agent alternatives in left.

KEVIN TOWERS: The former Padres' GM will be looking for a job just like any other free agent. His resume is powerful enough to attract the attention of several teams, including the Yankees.

Towers is close friends with Cashman, which makes it plausible, if not likely, that the executive will be hired as a high-level adviser in the Bronx. The Mets and Red Sox will interview Towers as well.

"I have that desire and that passion," Towers told the New York Times. "As much as I've enjoyed the time off, once spring training starts, I'm going to be itching to be out there ... it's still in my blood."

OMAR MINAYA: The Mets have lowered their sights for the rest of the off-season, which means it's up to Minaya to be creative. He'd love to shed Luis Castillo and open up a spot for Orlando Hudson, but that's easier said than done.

A more plausible scenario is a deal with Jason Marquis, a fairly competent alternative to John Maine or Mike Pelfrey as the No. 2 starter. Marquis, a 30-year-old lefty with a respectable 3.96 ERA at Coors Field last year, is from Staten Island, N.Y., and wants to pitch for the Mets.

Despite that wide-open door, Minaya has been less than aggressive in the pursuit of Marquis or any pitcher, including Randy Wolf, the market's second best starter, who would be a good fit at Citi Field.

Minaya currently is leaning toward jettisoning Carlos Delgado and going with Daniel Murphy at first base, although the power- shortage in left field is so critical, the Mets actually asked for the medical reports on Hideki Matsui.

JASON BAY: His preference is to remain at Fenway, but if the Sox are serious in their courtship of Holliday, don't be surprised if the left fielder gives serious consideration to the Mariners.

Bay fits for several reasons, not the least of which is he practically grew up as a neighbor in British Columbia. The M's will face stiff competition from the Angels and Cubs, but they're desperate for offense and could make a point of outbidding both. The obstacle they fear most, however, is the Yankees.

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