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5 Best/Worst MLB Trade Deadline Deals

By Ryan Mayer, CBS Local Sports

This week in the MLB has already seen a couple of big-time trades with the Royals, Blue Jays, and Astros putting their cards on the table and going all in for this season.  With the deadline looming at 4pm today, there's still plenty of time and some big names out their on the market to be dealt.  Will we get another blockbuster trade ala the Tigers three way deal that netted them David Price last season? In hoping we get a flurry of deals this afternoon, let's look back at some of the biggest (good and bad) MLB trade deadline day deals ever. 

Best Deals

These deals are being classified as best based on the performance that the player dealt gave their new team, or by what the team trading the big star got in return.  

5) Boston Red Sox trade Nomar Garciaparra in 4 team deal, receive Doug Mientkiewicz and Orlando Cabrera, and trade Henri Stanley for Dave Roberts. July 31, 2004

These deals are memorable because of the roles those three players had in helping the Sox win their first World Series since 1918.  Nomar was a fan favorite in Boston of course and it took guts for GM Theo Epstein to trade hime for guys that were mainly defensive ball players. But Mientkiewicz and Cabrera were huge in improving the Sox defense to allow them to make the magical run through the playoffs. Roberts of course had perhaps the season defining play in stealing second and sparking the rally against the Yankees in the 9th inning of Game 4.

4) Houston Astros trade Hunter Pence to Phillies for Jared Cosart, Jon Singleton, Josh Zeid and Domingo Santana July 31, 2011

This trade is one that keeps on giving for the Astros as they flipped Cosart for a couple prospects including Jake Marisnick who is currently patrolling CF for the 'Stros. Jon Singleton is considered one of the Astros top prospects, and Domingo Santana was just traded yesterday to Milwaukee for veteran reliever Mike Fiers. The Phils meanwhile, kept Pence for a year and a half before flipping him for a bag of beans. Yeah, I'm still bitter. Oh by the way the best part of this deal, the Phillies reportedly accidentally included Domingo Santana. They denied it but seeing as it's the Phillies, I tend to believe it. 

3) Boston Red Sox trade Manny Ramirez to Los Angeles Dodgers in 3 team deal, get back Jason Bay. July 31, 2008

Manny being Manny had run it's course in Boston at this point and the Red Sox were looking to move on.  They did just that moving him to Los Angeles. The Dodgers benefitted greatly. All Manny did was hit .396 with 17 HR and 53 RBI in 53 games for the Dodgers during the regular season.  Then in the postseason, Ramirez hit .520 with 4 HR and 10 RBI as the Dodgers made the NLCS before falling to the eventual champion Phillies. Pretty good pickup I'd say.

2) Philadelphia Phillies trade Carlos Carrasco, Lou Marson and Jason Donald for Cliff Lee and Ben Francisco. July 29, 2009

Okay, this technically wasn't a deadline day deal, but it's included because of the ridiculous postseason Lee had in leading the Phillies back to the World Series for the second consecutive year. In the regular season he was good for the Phils 7-4 3.39 ERA with 74 K and 10BB.  However, the postseason was even better. He was 4-0 with a 1.80 ERA 33 strikeouts to only 6 walks. The Phillies lost in the World Series but not for lack of effort from Lee. They of course would then trade him for nothing in the offseason because it's the Phillies.

1) Houston Astros trade Freddy Garcia and Carlos Guillen to Seattle Mariners for Randy Johnson and John Halama

Look, Garcia and Guillen were fine players for Seattle. But the Big Unit? He was nasty in Houston going 10-1 with a 1.28 ERA and 4 complete games while striking out 116 batters and walking 26 and leading Houston to the playoffs. That's ludicrous.


I'll say in advance these trades mostly cover trades the were awful for the team trading away guys in the long run.  Most of these teams were fleeced. 

5) Pittsburgh Pirates trade Jason Schmidt to San Francisco Giants for Ryan Vogelsong and Armando Rios. July 30, 2001

Schmidt was middling in Pittsburgh, 44-47 in 6 years, and not many were expecting him to do what he did in San Fran following this trade.  Schmidt over six seasons would go 78-37 with a 3.36 ERA, finished in the top 5 in the Cy Young voting twice and appeared in a World Series. Rios meanwhile would play only 78 games for the Pirates hitting .265 with 1 HR, while Vogelsong was 10-19 with a 6.00 ERA in parts of 5 seasons with Pittsburgh. To make matters worse, Vogelsong has gone back to the Giants and been productive. Not a deadline day deal which is why it's down a bit further. 

4) Philadelphia Phillies trade Curt Schilling to Arizona Diamondbacks for Travis Lee, Omar Daal, Nelson Figueroa and Vicente Padilla. July 26, 2000

Again not a deadline day deal but I'm still having nightmares about this.  Schilling wanted out of Philly (I can't blame him, the Phils had averaged 90 losses the previous four years and had lost 55 by the time he was traded) and the Phillies decided to move him to Arizona. All he did there was win a World Series, the World Series MVP and finish top 5 back to back years in Cy Young voting. Meanwhile the only truly useful player the Phillies got out of this deal was Vicente Padilla. Woof.

3) Atlanta Braves trade Neftali Feliz, Matt Harrison, Elvis Andrus, Jarrod Saltalamacchia and Beau Jones to Texas Rangers for Mark Teixeira. July 31, 2007

Look, there's nothing wrong with Teixeira, he's had a fine career. But the Braves traded for him to try and make the playoffs and they failed. While also giving up 4 prospects (Harrison, Andrus, Felix, and Saltalamacchia) that would make big impacts on the Rangers. Andrus is still there, while Harrison, Feliz, and Saltalamacchia aren't. But Feliz had 5 dominant years as the Rangers closer and Harrison had two very good years before getting hurt. Meanwhile, Tex was gone from the ATL after a year and a half. 

2) Seattle Mariners trade Derek Lowe and Jason Varitek to Boston Red Sox for Heathcliff Slocumb. July 31, 1997.

Lowe and Varitek became staples of the Red Sox teams that would win the World Series in 04 (both) and 07 (Varitek). Meanwhile, Slocumb went 2-9 over two seasons in Seattle with a 4.97 ERA. Yeah, fair to say Boston won here. 

1) Oakland Athletics trade Mark McGwire to St. Louis Cardinals for Eric Ludwick, TJ Mathews and Blake Stein. July 31, 1997.

Woof. All Big Mac did in St. Louis was hit 220 homers and give us the most memorable summer in recent memory with the home run battle between him and Sammy Sosa in 1998 when McGwire broke the single season homer record. Ignore the steroids. Don't lie you enjoyed that summer as much as I did. Meanwhile, Ludwick, Mathews, and Stein would combine for a 30-28 record in 396 innings with a 5.43 ERA for the A's. Not exactly what the wanted for a stud like McGwire.

Today's the day folks, some more teams will establish themselves as winners and losers by good or bad deadline day pickups.  Let's enjoy the fun.  

 Ryan Mayer is an Associate Producer for CBS Local Sports. Ryan lives in NY but comes from Philly and life as a Philly sports fan has made him cynical. Anywhere sports are being discussed, that's where you'll find him. Agree/Disagree? Thoughts, comments, complaints? Email or tweet him.  

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