On November 4th 2009, the New York Yankees captured their 27th World Championship against the Philadelphia Phillies. Since then, if you’re a fan of the other 28 teams, it’s been a slow, uneventful winter.

If you’ve been bored by the lack of activity on the baseball front, no need to worry: big things are going to start happening over the next few days. The Winter Meetings started today in Indianapolis, where General Managers meet with each other to talk trades, and agents come looking to get contracts for their available players. It’s a whirlwind of activity, and being in the age of Twitter, all it takes is one guy to spot two executives talking in the lobby, send a Tweet, and get the rumors rolling.

The possibilities are endless and there are thirty different agendas at play. Here are the big stories to track over the next few days:

Halladay Sweepstakes 2.0

When this summer’s trade deadline rolled around, Roy Halladay was the center of attention throughout sports talk radio and the blogosphere. Any fan of a contending team wanted to grab him to solidify a championship run, and the Blue Jays knew they could get back a ton of prospects in return to help revitalize the franchise down the road.

Unfortunately for Blue Jays fans who were looking forward to starting a much needed overhaul, the asking price in prospects was too high. The deadline passed, Halladay stayed in Toronto, and the decision proved to be the final nail in the coffin for General Manager J.P. Ricciardi’s run. The Jays had asked for too much, lost an opportunity, and now had nothing to show for their star pitcher with only one year left on his contract.

And so we’ve come to the subsequent winter, where the Blue Jays more or less need to trade Halladay. If they thought it was tough to maximize their value for him this summer, they’re going to find it’s even more difficult now. A trade this summer would have meant his new team got him for the stretch run to the playoffs, had his services in the postseason, and would get to bring him back for the final year on his contract in 2010. Now, a trade partner is only getting one year back.

This is creating a situation similar to what we saw with Johan Santana and the Mets in 2008. Santana had one year left and a no-trade clause: so while the Twins were looking to get prospects back before he departed, Santana was able to use his leverage to pick a landing spot that would give him a hefty contract extension. The end result was four prospects going to Minnesota, while Santana got a six year, $137.5 million extension to get his big payday.

It’s now about two years later, and Halladay is the one with one year left on his contract, and no-trade control. Whereas Santana more or less demanded an extension, thereby narrowing the Twins partners to the major market teams would could afford that contract, Halladay isn’t necessarily against the idea of pitching somewhere for one year, riding out his contract and becoming a free agent. But the Blue Jays are going to ask for top prospects in return, and if you’re the trade partner, you’re going to want a bit more than the one year of service in return.

Making this more complicated is the fact that Halladay will turn 33 years old next season . . . which means that you’ll be hard pressed to find a team willing to give up the level of prospects the Jays are asking for, plus a contract extension that would keep him employed at a high price through something like age 38 or 39. Ricciardi really painted them into a corner here.

The easy money bet is that he ends up on a major market team that could absorb the cost of his extension and hope for the best in his late 30s: this means the usual suspects like the Red Sox, Yankees, Angels and Dodgers (though there is a strong feeling in the rumor mill that Halladay does not want to play on the west coast long term). My guess is that Boston will be his most likely destination, though we shouldn’t rule out a possibility for a team to roll the dice, trade for Halladay’s services for one year and make a run for it, then let him hit the open market.

The Big Three: Holliday, Bay and Lackey

Since the winter started, Matt Holliday, Jason Bay and John Lackey have been getting most of the attention as the top prizes in this year’s free agent market. Holliday and Bay are both professional hitters who play left field, which actually gives teams with that need an option between two very good players. Bay is slightly older and hits for slightly less average, and is considered the worse defender of the two (though this is still a matter of debate in some circles). However, Bay has “proven” himself in Boston’s large market, while Holliday has only played in Colorado, St. Louis and Oakland (where he got off to a very slow start in his only American League experience). At the end of the day, Holliday will get a slightly longer and bigger contract, as the perception is that he’s a player you can build around and commit 6-7 years to. However, Bay is no slouch, and will give whatever team trades for him a reliable hitter in the middle of their lineup.

Lackey is the only clear cut “ace” of this free agent crop, though he’s fought minor injuries the last two years, and projects slightly below a #1 starter. Still, he’s earned his reputation as a tough, fiery competitor, and should be a welcome addition to any pitching staff. Lackey’s agent has used A.J. Burnett’s five year, $82.5 million contract as a benchmark his client should be able to eclipse (though I believe Burnett’s contract is more an example of the Yankees overspending, rather than his actual value). Still,  many around baseball seem convinced Lackey will get a $100 million contract, and I think he’ll get close. Unlike the competition for Holliday and Lackey, many contending teams could use a reliable, playoff tested starter like Lackey and will make a play for him: including the Yankees themselves.

Seattle Building a Contender

It’s easy to forget that the Mariners operate like a big market team, with a payroll hovering around the $100 million mark the last few years. It’s just that they haven’t spent that money wisely.

This winter, the mistakes of past management start to come off the books, as the hefty contracts for Richie Sexson, Adrian Beltre, Miguel Batista and others clear off (sadly, they are still stuck with Carlos Silva at $23 million for the next two years). New GM Jack Zduriencik impressed in his first year on the job in 2009, and now that he made the right steps to build the team back up, he may be seeing a prime opportunity to get back into the playoffs. He’s already stolen the division rival Angels’ longtime leadoff man Chone Figgins to take over at third base. Combine his skills with Ichiro’s, and now you’ve got what might be one of the best 1-2 punches of average, speed and on-base skills this side of Jeter and Damon. Combine with Jack Wilson at shortstop, and the left side of the infield isn’t going to let much through.

With all the money they now have to spend, the Mariners aren’t done at Figgins. Seattle will need some power to bring in those baserunners, and nearby British Columbia is where native Canadian Jason Bay was born and raised. The team also doesn’t have a commitment at DH, a position that is likely to have more players than open jobs for the second year in a row. Hideki Matsui is considered the most likely player to fill this role, thanks to Seattle’s close ties to Japan. If you saw the World Series, you know Matsui still has something left in the tank, though his next employer will want to keep him away from the outfield.

Oh, and if they’re not done there, the team has also been rumored to be going after John Lackey. The Mariners may very well snap the Angels’ run of winning the division five of the last six years, using their own former players against them.

Meet the Mess

If you’re a Mets fan, the 2009 season began with high hopes from Putz and K-Rod reinforcing the bullpen . . . but things quickly deteriorated as injuries stacked up, and team morale sinked to new lows. Reyes, Beltran and Santana are all expected to show up at Spring Training healthy and ready to compete, but expectations are lower this time around (especially with the already strong Phillies starting 2010 with Cliff Lee as their ace).

It’s not all doom and gloom, however. The Mets still have some of the top premiere players in the game in David Wright, Carlos Beltran, Jose Reyes, Johan Santana and Frankie Rodriguez. Unfortunately, it’s the supporting cast that needs some serious work. With a brand new stadium asking top New York prices for tickets, and the juggernaut in the Bronx overshadowing the team from Queens, the pressure will be on General Manager Omar Minaya and Manager Jerry Manuel to perform. If not, both will find themselves out of a job by this time next year.

The Mets have been linked to Matt Holliday and John Lackey before the World Series even ended, but it seems more likely that the team will spread around their money instead: bringing in players like Joel Pinero, Randy Wolf and Orlando Hudson. In past years, the Mets always looked to make the “big splash” in the free agent market to show commitment to fans when they fell short. And while the public relations department would probably like a distraction to wash away the memories of 2009, the strategy of building around their talented core with a higher quantity of support talent as opposed to another expensive star or two makes far more sense.

Quick Hits

The Braves’ crowded rotation could mean a new bat. Atlanta didn’t wait until the meetings to fortify their bullpen, signing veteran relievers Billy Wagner and Takashi Saito to close out their games. Between Tommy Hanson, Tim Hudson, Kenshin Kawakami, Derek Lowe, Javier Vasquez and Jair Jurrjens, they have one quality pitcher too many in their rotation. Most expect them to move Javier Vasquez, who had a fantastic 2009, has a reasonable contract and could net a big bat.

Tigers looking to deal. Management swears they’re not trying to slash payroll, but the Tigers have been very loud about their desire to trade both Edwin Jackson and Curtis Granderson this winter. The Central is winnable as always, but pay close attention to what the team gets in return. The Tigers insist they have no desire to trade Miguel Cabrera, but if they go younger and look to rebuild, he can’t factor into their future plans. If Detroit is out of the running this summer, expect the Red Sox to come calling for the consistent Cabrera.

A-Gone staying home? It made all the sense in the world for the Padres to trade Adrian Gonzalez this past summer. When it didn’t happen, the common perception was that he’d be dealt come winter. However, if you believe the buzz coming out of San Diego, the star first baseman is going to stay put . . . at least through the summer trade deadline, when the rumor mill will start all over again. Gonzalez would fit the Red Sox so well that a trade seems inevitable, but it may take a while longer to happen.

Who wants to play with Milton Bradley? When the troubled outfielder got a big contract from the Cubs following a tremendous 2008 season, many within baseball were skeptical. Well, here we are one year later, and the Cubs have made it clear that come hell or high water, Bradley has seen his last days in a Cub uniform (with two years to go on his contract). The Rangers and Rays seem to be the most likely destinations, with Chicago picking up much of the tab.

We’re in the age of new media, so enjoy the Winter Meetings as they happen. Root for your team to make solid decisions, but try not to get too wrapped up in every rumor Tweet you see. And expect the unexpected: every year, there seems to be at least one major move no one sees coming.

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