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#pounditThursday, March 28, 2024

10 Worst Deadline Deals of the Decade

Note: This is something I posted two years ago at my blog on Fox Sports before I had started this site. Since I put so much time into it, I felt it was worth sharing here (and I’ve copied and pasted word-for-word).

In light of the upcoming baseball trading deadline, I came up with a list of the worst (most one-sided) deadline deals of the decade. Hopefully this should serve as a cautionary tale for GMs before they go out and sell off their teams and get nothing in return, or on the flip side, acquire a useless player and give away superstars in the making. The list takes two factors into account. The first is how much the acquired player helped/has helped the team that acquired him. The second is how little was given away in return. Feel free to comment if you disagree with the order or if you would like to add to the list. Keep in mind, this is strictly a trade deadline list since 2000.

10. Jeremy Bonderman to the Tigers – (July 5, 2002)
This is one of the more one-sided 3 way deals around. In 2002, the A’s sent Carlos Pena, Franklyn German, and a player to be named later to the Tigers. The A’s got back a year and a half of average starts from Ted Lilly and 2 minor-leaguers from the Yankees. The Yanks got one and a half less than mediocre years from the now defunct Jeff Weaver. Of course, the wild card in the deal, Jeremy Bonderman became the player to be named later. Bonderman has had the longest tenure with the team to whom he was traded of all the players involved in the deal. By 20, he had already pitched a full season in the bigs. Now at 23, he’s begun to dominate teams.

9. Aramis to the Cubs – (July 23, 2003) At the time of the trade Aramis Ramirez had already been a 30 homer/100RBI guy at the hot corner for the Pirates, and he was only 25 years old! Such talent and prowess would ordinarily command slightly more than Jose Hernandez, Matt Bruback, and a player to be named (Bobby Hill), but not in the case of this trade. Not only did the Cubs get Ramirez from Pittsburgh, but they also received Kenny Lofton who is still a productive major leaguer and cash in the deal. Since the deal, Aramis has already smashed over 100 homers with the Cubs and has hit over .300 twice. Quite a steal.

8. Indians get Sizemore, Lee – (June 27, 2002)
Ordinarily this wouldn’t have been such a poor trade. Bartolo Colon, a Cy Young winning pitcher, for Grady Sizemore and Cliff Lee (and Brandon Phillips and Lee Stevens). The only problem with the trade is that Omar Minaya mistakenly identified the Expos as a contender in 2002 while he was running the team on behalf of MLB. Colon pitched as well as expected for the Expos, winning 10 games in one half of the season. Only problem, the Expos were a pretender, and Minaya gave away an All-Star in Sizemore, and a pitcher who’s averaged 16 wins over the past two seasons in Lee. This would’ve been a triply bad trade if the Indians hadn’t given up on Phillips so soon. Still, Shapiro benefited well.

7. Scott Kazmir to the Devil Rays – (July 30, 2004) In a desperate move, the Mets under GM Jim Duquette, felt the pressure to make a move when they decided they were in the playoff hunt. In reality, they weren’t close to the playoffs, and certainly, Victor Zambrano wasn’t the guy to put them over the edge. Granted, Victor Zambrano was the best pitcher the Devil Rays had at the time, but that’s like saying “she’s the hottest girl in my aeronautical engineering class.” Zambrano was already injured at the time of the trade, and he promptly went on the DL. Since the trade, Scott Kazmir has developed into an All-Star at the young age of 22, and has only room to grow. Imagine that, Zambrano may never pitch again, and Scott Kazmir looks like a perennial All-Star.

6. Michael Young to Texas – (July 19, 2000)
This 3-time All-Star and hits machine escaped Toronto in 2000 along with Darwin Cubillan for Esteban Loaiza. The Blue Jays were looking for a boost at the trading deadline to compete with the Red Sox and Yankees, and wound up finishing 4.5 games out. Loaiza pitched 2 and a half sub-par seasons for Toronto. The worst part, the year after the Blue Jays let Loaiza go, he won 21 games with a sub-3.00 era, and had the best year of his career! No matter how you slice it, the Rangers got a stud in Young for a very cheap price

5. Carlos Beltran to the Astros – (June 24, 2004)
3 way deal between the Astros, A’s, and Royals sent Beltran from small-market hell in KC to a legit contender in Houston. This is the poster-child for what a great deal can do for your team mid-season. Beltran played 90 games for the ‘Stros, homering 23 times, just below once every fifteen at-bats. He lead the Astros to the wild card and NLCS and had a legendary playoff performance. He stepped up his game, smashing 8 homers in 12 playoff games, driving in 14 runs, scoring 21, and hitting .435 in the process. Meanwhile, the other players involved in the deal have been useless. They include the injured Octavio Dotel, John Buck, Mark Teahen, and Mike Wood.

4. Contreras to the White Sox – (July 31, 2004) After opening the cash register to sign Contreras as a free-agent from Cuba, the Yanks panicked and gave up on him after just 27 starts. They pawned him off to the White Sox for Esteban Loaiza, a sheer sign they were sick of his mediocrity, injuries, and disappointment. A year later Contreras seemed to have found himself and became an integral piece in the White Sox World Series victory, not to mention one of the top pitchers in the league. Oh yeah, can’t leave out the fact that the Yankees grew so dissatisfied with Contreras that they paid the White Sox to take him off their hands. Way to go on that trade Kenny.

3. Schmidt to the Giants – (July 30, 2001) I don’t believe anyone has accused the Pirates of being frugal at the trading deadline, but they were extra generous in 2001. They gave up fireballer Jason Schmidt, whose talent theycompletely misjudged, for ugatz that year. While Schmitty became a Cy Young contender in each year after the trade, I hardly believe anyone knows the whereabouts of the players for whom he was traded- Armando Rios and Ryan Vogelsong.

2. Rolen to the Cards – (July 29, 2002)
Rolen is a baseball player of the highest degree. Simply said, he is one of the best defensive and offensive third basemen in the game, possibly of all-time. The Phillies should’ve made more efforts to sign him long-term; he’s too good to give up for Placido Polanco, Mike Timlin, and what was thought to be the prized-prospect in the trade, Bud Smith. Anyone hear from him since the no-hitter? Didn’t think so- Rolen’s still hitting .300 with power, winning gold gloves, and going to the playoffs ever year.

1. Schilling to Diamondbacks, Red Sox
(July 26, 2000)
Schilling from the Phillies to the Diamondbacks for Omar Daal, Nelson Figueroa, Travis Lee, and Vicente Padilla. Forms one of the best 1-2 punches in baseball along with Randy Johnson, leading the D-Backs to a World Series victory the next year.

(November 28, 2003) Sent from the Diamondbacks to the Red Sox for Casey Fossum, Brandon Lyon, and Jorge de la Rosa. Goes on to lead the Red Sox to a World Series win the next year. Notice a trend?

Also, no team got anything decent back in exchange for Schilling, amazing!

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