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With Boras at his side, look for Holliday to go to AL

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Jon Paul Morosi

Jon Paul Morosi is a national MLB writer for FOXSports.com. He previously covered baseball for the Detroit Free Press and Seattle Post-Intelligencer. He began his journalism career at the Bay City Times in his native Michigan. Follow him on Twitter.

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Updated Nov 16, 2009 1:18 PM ET
     
 
Only a handful of teams have the resources and desire to sign Matt Holliday. In that sense, the market for the left fielder's services is quite small. But it's plenty big enough for Scott Boras to exploit. And you can bet that Holliday will end up with the contender who offers the most money. The Yankees, who need a left fielder, are interested. The Red Sox, who need a left fielder, are interested. The Angels, who need a power bat, are interested. So, I fully expect Holliday to play in the American League next season. The highest bidder will determine where. He won't be back in St. Louis, where he finished this season and seemed so comfortable in the process. Surprised? You shouldn't be. Boras clients — along with most ballplayers and most people in this country — affix their signatures to the biggest offer they can find. It's very hard to find fault with that. The prelude to the Holliday bidding reminds me so much of Mark Teixeira's voyage into free agency one year ago. I'm not talking about the eight-year, $180 million contract he signed, although Boras would love a repeat of that. Instead, it's the exclusivity and financial means of the group that has a real chance to sign Boras' latest franchise slugger. The Mets are this year's Nationals, a team that will make an offer because it must. They don't look like certain contenders in 2010, so they won't win the prize. But thanks for checking. The Giants and Mariners? They are coming off improved 2009 seasons and would benefit greatly from Holliday's power. But I can't envision either of them outbidding the three AL powers, particularly when faraway left field fences would be tacit in both offers. The Cardinals, meanwhile, have yet to make a formal contract offer. Once their exclusive window passes without a deal — and it will — they will merely become one of 30 teams with a chance to bid on Holliday. No more. No less. On Friday, I spoke with someone who has knowledge of the developing Boras/Holliday plan. I asked if he believed the Cardinals would be given any special preference, based on Holliday's time in St. Louis this year.
Nope. "He was there two months," the person said. "St. Louis is a good place to play — a great city with a good fan base. But do I think it holds any special significance to him? No." Translation: If the Cardinals want Holliday to protect Albert Pujols again in 2010, they will need to cut the biggest check. And the folks in St. Louis simply don't spend like the Red Sox and Yankees. Last winter, the old rivals were the final two teams in on Teixeira. Boston's bid stopped at eight years and $170 million. New York's went $10 million higher. On such a large scale, that's not a huge difference: around $1 million per year when spread over the lifetime of the deal. But the gap was big enough to matter. And in truth, the Yankees needed Teixeira worse than the Red Sox or Angels did. So, they got him. If history is about to repeat itself, then Holliday will be en route to Boston — provided, of course, that Jason Bay signs elsewhere. The Red Sox have a greater need for a Holliday in 2010 than either the Yankees or Angels. Their core is about to turn over, and they have an obvious opening for a right-handed slugger (provided Bay doesn't return). Brian Cashman of the Yankees and Tony Reagins of the Angels have more flexibility (right now) than Theo Epstein, who must work around David Ortiz as a full-time designated hitter. All three GMs can tell Boras that they are also shopping in a trade market that suddenly includes Detroit's Curtis Granderson, who has played left field in the past and would probably be willing to do so again. A robust trade market could harm Boras' leverage, but he will be in command again if Bay, represented by Joe Urbon, signs before Holliday.

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Boras' dream scenario would probably involve Bay hooking onto a West Coast team — perhaps the Mariners or Giants — by the middle of December. That would leave Boras plenty of time to pit the AL heavyweights against one another. Still, a number of executives and scouts told me Friday they believe St. Louis is the best overall fit for Holliday. I can't dispute that. It's a one-newspaper town with a devoted, forgiving fan base that is close to where Holliday grew up (Oklahoma). If Holliday struggles in April while playing in Boston or New York — like he did this year with the A's — there will be boos and second-guessing. Life would probably be less complicated in St. Louis. The Angels could represent a happy midpoint — big enough to garner plenty of attention, relaxed enough to let him breathe, an organization that wins routinely and should be back in the playoffs again next October. "Matt is not a big city, flashy guy," said one executive who knows Holliday. "He loves his family and baseball and does not seek the limelight. He is better suited for cities like Seattle, St. Louis and Los Angeles than in the media pressure cookers of Boston and New York." One scout pointed out that Holliday knows the pitchers, cities and ballparks in the National League much better than he does in the American League. Very true. But this isn't like picking a college. Comfort and geography are very important, right up until you consider all that money and the near promise of postseason baseball. Ask CC Sabathia. For reasons understandable and justifiable, we should expect Holliday to sign the biggest contract he's offered. And I'm almost certain that means he will be playing left field for the Red Sox, Yankees or Angels.
Tagged: Matt Holliday, Mark Teixeira, Giants, David Ortiz, CC Sabathia, Red Sox, Angels, Albert Pujols, Curtis Granderson, Tigers, Yankees, Mets, Jason Bay, Mariners, Cardinals

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