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Might the Cardinals let Holliday and Boras pull a “Drew” on them?

Here is the environment. The St. Louis Cardinals want Matt Holliday back. All indications are that the outfielder and his agent Scott Boras are heading out into the open market. Boras has made rumblings that he is looking for a Mark Teixeira-kind of contract.

Last winter, the first baseman signed with the Yankees for eight-years, $180 million. That may be a neighborhood in which the Cardinals would not want to live, especially with an Albert Pujols extension that looms even larger still in the planning stages.

From the Cardinals perspective, their direction for next two years seems clear, but things get fuzzy after that. Pujols, who may not be motivated to sign a new offer any time soon, has two years remaining on his current deal.

What happens after 2011?

Manager Tony La Russa is not under contract for 2010, but is expected to return. For at least the last 20 years, he has always signed either two or three-year deals. A new two-year commitment would take La Russa through 2011, like Pujols.

Chris Carpenter is also locked up through 2011, though the club holds a 2012 option. Early in the 2012 season, the ace will turn 37 and has a history of physical problems. Ryan Ludwick will be first-time free agent eligible following the 2011 season, as well.

No matter what happens, the Cardinals 2012 cupboard should not be entirely bare, however. Catcher Yadier Molina and emerging co-ace Adam Wainwright should be around through at least 2012 and 2013, respectively.

Still, in deciding whether or not to sign with St. Louis, could Holliday have concerns about the club’s competitiveness following the 2011 season? Though he would likely never settle for a two-year deal only, there is another possibility – build an early out into a longer-term contract.

It is a strategy Boras has used to his advantage in the recent past.

Boras clients and opting out

During the 2007 World Series, the agent announced that Alex Rodriguez was opting out of his contract with the Yankees due to concerns over the club’s future direction. Of course, it was merely a negotiating ploy to get the New Yorkers to pay more for A-Rod’s services.

It worked to the tune of ten years, $275 million, a new MLB record. It eclipsed Rodriguez’ own ten-year, $252 million deal signed with Texas, of which he completed seven years before tearing it up and starting over.

A year earlier, Boras left the Dodgers high and dry when he sold high on former Cardinals outfielder J.D. Drew. Having led Los Angeles with 100 RBI in 2006, Drew then bailed out of the final three years, $33 million remaining on his five-year, $55 million Dodgers contract.

Dodgers general manager Ned Colletti was understandably angry, stating that Drew had “changed his word”. He also noted that Boras never asked for Drew’s contract to be re-negotiated before they bolted onto the open market.

A free agent again as he was two years earlier, Drew re-emerged as a member of the Boston Red Sox. His new deal was for five years, $70 million.

I have often wondered if Boras’ and Manny Ramirez’ shady act to get Manny out of Boston and into a Dodger uniform wasn’t some kind of payback for the Drew escapade. Even if not, every new contract means a bigger cut for the agent. He never loses – he just wins less on rare occasions.

But back to Holliday and the Cardinals.

Could the wishes of the player, his agent and the club come together to enable a four-, five- or even six-year contract with an out after just two years? Why not?

The slippery slope

If the Cards gave such a deal to Holliday, why would not Albert Pujols expect the same kind of structure? After all, Pujols has been the most vocal of Cardinals players about wanting to ensure the organization fields a competitive team on an ongoing basis.

In fact, maybe Holiday and Pujols could time their perpetual two-year outs to align, regularly holding a pair of big guns to the heads of Cardinals ownership to keep the team strong – or else! La Russa could hang with the bi-annual plan as long as cares to, as well.

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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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