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Top Five: Trade Deadline Gambles Since 2000

As the Cardinals make their yearly stabs at a big July 31 move, a look at some of their biggest trade deadline moves of the past decade.

Since returning to prominence in 2000 and staying there, for the most part, ever since, the Cardinals, especially under Walt Jocketty, have been as closely associated with the deadline deal as any team in baseball. That reputation may in fact be overblown—sometimes the big late-season acquisition is Mike DeJean, sometimes it's Matt Holliday—but St. Louis, more than any other perennial buyer, is linked with the concept of trading prospects for rentals.

Sometimes it works out; other times it's Mark DeRosa

5. 8/6/2004: Cardinals Trade Jason Burch, Chris Narveson and Luis Martinez for Larry Walker

Maybe the least risky deadline move of all—I can't remember anyone saying at the time that the Cardinals would come to rue the day they traded Burch, a relief prospect who flamed out in the high minors, or Chris Narveson, who's only now earned a major league roster spot with the Brewers, and who would later return to the Cardinals on waivers, anyway. 

The most telling part of this trade is Luis Martinez, whom the Cardinals had picked up on waivers the offseason before. Martinez, a left-handed pitching prospect who made four late-season starts with the Brewers in 2003 and later pitched in Japan, ended up on waivers because he allegedly shot a man twice in the Dominican Republic. So not only was one of the two key pieces of this trade available on waivers six months before it happens, he was available on waivers because the police were trying to determine if he had committed attempted murder.

Larry Walker, meanwhile, was 37 and extraordinarily injury prone, but he was also hitting .324/.464/.630. As gambling goes, this is like betting on the Harlem Globetrotters.

4. 6/27/2009: Cardinals Trade Jess Todd and Chris Perez for Mark DeRosa

There were a number of potential problems the Cardinals couldn't really have anticipated with this trade, and they ended up hitting on all of them, no matter how ridiculous. 

Problem one: That Ryan Franklin would struggle down the stretch for the third year in a row. This one could have been anticipated, but only because Cardinals fans are a very distrustful lot as it relates to bullpen guys. Jess Todd, long-time favorite of the hyperventilating prospect geek fraternity, and Chris Perez, long-time favorite of people who like high strikeout rates, might have been useful changes of pace when Franklin's fastball-on-the-corner game plan expired in August.

Problem two: That Mark DeRosa might struggle to hit like he has his entire career. Suffering a career-threatening wrist problem during one's first week on the roster is both a bad way to make a first impression and an unlikely one, but that's exactly what happened. And so DeRosa failed even to outhit the Cardinals' sorry 2009 third basemen, who to that point had been paced by Mr. Joe Thurston.

Problem three: That the Cardinals would make a subsequent move which totally canceled out DeRosa's famous versatility, leaving him to play third base exclusively. Okay, this is the ridiculous one. Whatever your thoughts were of the prospects the Cardinals gave up to acquire DeRosa, it was clear on June 27 that they were a nearly perfect team to utilize his strengths. On June 27 they were playing a left-handed platoon of futility in the outfield and a left-handed outfielder at second base; in either spot he could spell poorly matched hitters without giving up defensive value. 

By July 24, DeRosa having played in just 10 games, the Cardinals had traded one of those left-handed outfielders for Julio Lugo, who took over in the platoon at second base, and acquired Matt Holliday to play every day in the outfield. And suddenly Mark DeRosa was a third baseman with a career-threatening wrist problem. 

3. 7/29/2002: Cardinals Trade Placido Polanco, Bud Smith and Mike Timlin for Scott Rolen (and Doug Nickle)

This one gave me a real sense of foreboding when it happened, but in hindsight that was just because I was a huge fan of Bud Smith. Bud—it feels wrong to call him Smith—arrived in the major leagues at 21 acting like 30 year-old Tom Glavine. Then he pitched a no-hitter, and while history will lump him with the Jose Jimenezes of the world Bud Smith's was different; he arrived in St. Louis having put together a 17-2 record between AA and AAA in 2000, and the day after his no-hitter his career Major League line was 4-2 with an ERA of 3.75. 

Placido Polanco, of course, went from an empty .300 hitter to a startlingly consistent, surprisingly powerful empty .310 hitter, making this deal a little less embarrassing than it seemed like it might be in 2003; he's put up 28.8 WAR since the trade, and netted the Phillies the immortal Ugueth Urbina in 2005. OK, maybe that makes it more embarrassing. 

For the Cardinals' troubles, they got three and a half prime years out of one of the best third basemen who ever lived. And Doug Nickle!

2. 2006-2008: Cardinals think about trading Colby Rasmus for Anybody, including but not limited to Dontrelle Willis

For a prospect who for three and a half uninterrupted years was the top player in the Cardinals' system Rasmus spent a lot of time either underperforming, as he did in 2008; being passed in the system, as happened when Rick Ankiel did his brief and incredibly entertaining Smoky Joe Wood impression; and getting traded in the radio and on blogs, as happened whenever an interesting player was available. 

The one that will always stick in my mind, though, is a trade that briefly gathered Hot Stove steam in the winter of 2006—Colby Rasmus for Dontrelle Willis. To be sure, Willis was, at the time, nearly as entertaining to watch as Rick Ankiel, and as long as Albert Pujols is around the Cardinals will always seem just one outstanding pitcher away from lasting invincibility. 

But while Willis was no Roy Oswalt, and Rasmus was closer than Shelby Miller is now, there were times when I, a card-carrying HPGF member, thought to myself: Dontrelle Willis would be very entertaining in a Cardinals uniform. And Colby Rasmus—why, I haven't even seen him yet. If anything gives me pause about trading Shelby Miller, the Cardinals' latest undisputed top prospect, it's this trade that almost was.

1. 7/24/2009: Cardinals trade Brett Wallace, Clay Mortensen, and Shane Peterson for Matt Holliday

And if anything makes me feel like it wouldn't be so bad, it's this trade that actually was! Brett Wallace always seemed 120 feet away from the trading block—the minute it seemed unlikely he would stick at third base, he was doomed to leave St. Louis for Pujols-less pastures. But it was still a surprise, if not a big one, to see the Cardinals include him as part of a blockbuster deal that bought them two months of Holliday. 

So much was at stake here, and so much of it has turned out well as of year one—the Cardinals traded their top prospect and one of the pitchers nearest the top of their stack of back-of-the-rotation right-handers, and they did it knowing that they'd have to sign Holliday to an enormous deal to justify it. Holliday was signed, after some concerning moments, and while Clay Mortensen is having a fine season in the PCL neither he nor Brett Wallace, hitting .300/.362/.510 for the Toronto Blue Jays' AAA affiliate at a hitters' park in a hitters' league, have made them regret it. 

Of course, we've got six years left to judge this—six years of $17 million Holliday on one end, and six years of team-controlled Clay Mortensen and Brett Wallace on the other. And that's what makes trade deadline moves such a gamble; a team is often paying for two months of performance, but the prospect installment plan means the effects could last years.