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12/04/09 1:02 AM EST

Winter Meetings to bring some answers

Moves will get done during this year's gathering in Indy

One of the great things about Major League Baseball's annual Winter Meetings is that, without fail, at least some of the questions that have been hounding fans, executives, players and agents will get answered in the course of a whirlwind four days.

Then again, there are two more months until pitchers and catchers report to Spring Training, so there's still plenty of time to make moves.

But heading into this year's Meetings, which descend on Indianapolis on Monday, some big-ticket items on the to-be-taken-care-of lists of all 30 clubs will be crossed off and we'll have a better idea of who we'll see on the field come April 2010.

Here are some of the biggest questions that need to be addressed before the wheeling and dealing begins in Indy:

Where will Roy Halladay end up?
The Jays are looking to trade Toronto's ace. This we know. But the where and when of the situation is unknown, and the package of prospects and big league players that it will take to lure the former Cy Young-winning right-hander away from new Blue Jays general manager Alex Anthopoulos figures to be one of the huge topics buzzing around the Indiana Convention Center. We've heard about the Red Sox and Yankees and maybe the Angels or Phillies or Dodgers. Anthopoulos and his assistants will likely spend a good deal of Winter Meetings week holed up in their hotel suite, assessing offers that could set up a division rival to get even stronger while at the same time shape the Toronto franchise for the next five to 10 years.

Who will land the biggest bats in Jason Bay and Matt Holliday?
The Red Sox don't want to lose Bay, their best slugger from 2009, but Holliday, who played for the Oakland Athletics and St. Louis last year, might be an option for them if Bay decides to walk -- and rumors that Seattle is pushing hard for the British Columbia native heated up again on Thursday. Then again, most of the high-payroll teams have been mentioned as being interested in one or both of these Type A impact hitters, so expect a contending team to get even more robust in the middle of its lineup, and expect it to happen soon.

Who will sign the top free-agent pitcher, John Lackey, and how will that affect the market?
Lackey's 31 years old and coming off two injury-shortened seasons, but he's also got a win in Game 7 of the World Series (2002) to his credit, more than 100 big-league victories and a reputation as a fierce competitor who always wants the ball in the big game. What does this mean? Well, if the Angels don't re-sign him, expect Lackey to land in the hands of a team with a lot of money to spend, because he's probably looking for at least five years and at least $15 million per season. If Lackey can't get that type of deal, it will be interesting to see how that ripple affects the other available starters such as Ben Sheets, Rich Harden, Erik Bedard and Randy Wolf.

What will the world champions do?
So many rings and so many questions for the New York Yankees, fresh off their 27th World Series title. If the Bronx Bombers decide to trade for Halladay, which remains a strong possibility according to the daily Hot Stove stewing, their bullpen will probably lose Joba Chamberlain, Phil Hughes or both, which would make a few dips into the plentiful relief-pitching pool a necessity. Meanwhile, where are World Series heroes Hideki Matsui, Johnny Damon and Andy Pettitte going to end up? And if the Yanks lose any or all of them, how will they replace them? And for how much?

And what about the runners-up?
The Phillies have already made some waves, letting third baseman Pedro Feliz head out of town via free agency while replacing him with Gold Glover -- and former Phillie -- Placido Polanco. It's no secret that the Phillies would like to bolster their starting rotation, and they already kicked some serious Toronto tires regarding Halladay last year, ultimately trading for Cliff Lee instead. Getting a Halladay deal done would serve notice that they're more than ready to mix it up with the American League champion in a third straight Fall Classic.

And what about the Red Sox?
The Red Sox last won it all in 2007, but they came close in 2008 before being swept by the Angels in the first round this past season. They want revenge, and it starts with general manager Theo Epstein and his lieutenants working their winter magic like they have in other years. The Sox missed out on Polanco so far, but they've already agreed with Marco Scutaro on a two-year deal, pending a physical, and they head to Indy looking for a bat. It might simply be Bay, or it might be Adrian Gonzalez, the Padres' slugging first baseman Epstein has coveted for the last three years. And then there are the Halladay-to-Boston rumors, which simply won't go away.

What will Scott Boras wear?
This one's easy to answer. The agent who always seems to have a handful of hugely important clients during these Meetings rocks a blazer, a button-down shirt and jeans, in addition to plenty of smiles when his players get their deals. This year, Boras will be offering the services of Holliday, Damon, third baseman Adrian Beltre, pitcher Jarrod Washburn, reliever Mike Gonzalez, infielder Felipe Lopez, outfielder Xavier Nady, catcher Ivan Rodriguez and more.

Where does the other New York team fit in?
Yes, the Mets struggled mightily last year, falling victim to a roster full of injuries and underperformance. Now GM Omar Minaya has the task of rebuilding in a hurry and getting his team back to the top of the National League East, which features the dominant Phillies and up-and-coming clubs in Florida and Atlanta. So where will they start? Maybe right at the top of the pitching heap with Lackey, or right at the top of the hitting pile with Bay or Holliday. Bottom line: The Mets are ready to do what they have to do to improve, and they need improvement in quite a few areas.

Will the economy be as much of a factor as it was last year?
There weren't exactly tumbleweeds blowing through the Bellagio Hotel and Casino at last year' s Meetings in Las Vegas, but by the time mid-January rolled around, over 100 free agents still didn't have jobs, and many seasoned players -- Frank Thomas, Jim Edmonds, Ray Durham -- never signed. It was weird and it was a sign of the recession that was gripping the country as a whole, but there have been signs of improvement with the signings and salaries we've seen so far this fall. We'll see what happens next week in America's Heartland.

Will any surprise moves become the story of these Meetings?
You never know what might happen at the Winter Meetings. Not only is there the Rule 5 Draft, which in the past has produced stars such as Johan Santana, Josh Hamilton, Joakim Soria and Shane Victorino, but clubs can get bold. If Seattle decided to give up on extension talks and deal arbitration-eligible starter Felix Hernandez, for example, that would be the talk of the entire Meetings and perhaps the entire winter. The same would apply to Boston if it dealt closer Jonathan Papelbon. For other surprises, just wait until October, when we'll find out if seemingly under-the-radar moves pay off in the postseason.

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