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The Cardinal Nation Blog top stories of 2009 #4: Holliday’s free agent romp

For the ongoing services of outfielder Matt Holliday, the St. Louis Cardinals and agent Scott Boras carried out an intricate dance for months.

    Making a quick playoff exit was not what the St. Louis Cardinals had in mind when giving up three top prospects for the final two and a half months of Matt Holliday’s expiring contract. Making matters even worse was the reality that the outfielder’s agent, Scott Boras, was plotting the course, a man with a well-deserved reputation for finding top dollar for his clients via free agency.

    John Mozeliak, Matt Holliday, Bill DeWitt Jr., 01/07/10 (AP/Jeff Roberson)The situation would remain front and center on the minds of the Cardinal Nation from July through the end of 2009. In fact, it remained topical right up until January 5, when Holliday came to terms on a new, seven-year, $120 million deal with an eighth-year option to remain with St. Louis.

    It was a long and painful journey to get there.

    From his very first meeting with the press as a Cardinal, a session I attended on July 24, Holliday was asked, then later asked and re-asked about his future plans. The now-30-year-old made it clear from the start that he was in no hurry to discuss a long-term contract.

    As the Cardinals season moved toward its close, it was unclear whether or not Boras and the club had yet spoken regarding the matter. On September 24, Boras laid down the law by telling the media he was looking for a Mark Teixeira-like, eight-year, $180 million deal for the man he labeled a “blue-collar superstar”.

    Holliday Cardinals futures took a severe beating in fan markets as a result. Into the off-season, Boras hoped to interest the deepest-pocketed teams in New York, Boston and Los Angeles in the bidding.

    By early November, when Holliday officially filed for free agency, the Cardinals had seemingly lost whatever small advantage they previously may have enjoyed. Holliday was rumored to have said he would not be giving the club preferential treatment. Chairman Bill DeWitt Jr. acknowledged his Cardinals would not be the high bidder even as the Angels, Giants and Braves stated they were not interested.

    The Cardinals offered Holliday arbitration at the start of December, which was rejected as expected. Boras toughened his stance, pulling the St. Louis future of Albert Pujols into the fray. By mid-month, the Cards made their first reported formal offer, rumored to be five years at about $16 million per year, but apparently received no reply.

    As the Jason Bay talks with the Red Sox stumbled, that club expressed interest in Holliday. In fact, it later came out that Boston made him a five-year, $82.5 million offer before giving the same deal to pitcher John Lackey, who accepted. Their AL East competitors from New York never got into the mix, though the Mets at least tried to leverage Holliday in their own Bay negotiations before finally landing their initial target.

    As December came to a close, a rumor surfaced that Baltimore offered Holliday eight-years, $130 million guaranteed. A number of other sources, including the Orioles team president, shot down the report. In hindsight, a number of industry-watchers felt the Cardinals gave the outfielder too many years, therefore spending too much in total. Perhaps the Baltimore rumor hastened that.

    After a meeting between Cardinals executives and Boras in Austin, Texas the first weekend of January, it took only a few more days to lock down the deal, thus ending one of the most up-and-down free agent sagas the Cardinal Nation has ever had to endure – until Pujols nears free agency, that is…

    Link to The Cardinal Nation Blog’s top 20 stories of the year countdown

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    Brian Walton

    Brian Walton runs The Cardinal Nation and The Cardinal Nation Blog, covering the St. Louis Cardinals and minor league system.
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