The 10 worst trade deadline deals in MLB history

The danger in acquiring a player close to the MLB trade deadline is always the unknown potential that a contender might be giving up. There are many occasions where the prospect may not pan out, but there have also been plenty of examples to cite the opposite. Here’s a look at that list, and the top 10 trades that MLB teams wish they probably hadn’t made at the trade deadline.

Mark McGwire

10. Oakland A’s send Mark McGwire to the St. Louis Cardinals for Eric Ludwick, T.J. Mathews and Blake Stein – July 31, 1997

Neither Oakland nor St. Louis was in playoff contention in 1997, but the Athletics determined they would not be able to afford McGwire after the season and wanted something in return for the slugger. St. Louis got 24 home runs from McGwire over August and September, then 70 home runs in 1998. As for Ludwick, Mathews and Stein? Mediocre pitching for the A’s over the next few seasons.

Aramis Ramirez

9. Pittsburgh Pirates send Aramis Ramirez, Kenny Lofton and cash considerations to the Chicago Cubs for Matt Bruback, Jose Hernandez and Bobby Hill – July 22, 2003

The Pirates determined they would not be able to afford the $6 million that Ramirez, then just 25, was due in 2004, so they shipped him, along with Kenny Lofton (and cash, for some reason) for a trio of players that did nothing to help move the Pirates toward a winning record. Hernandez, known more for his ability to strike out rather than actually hit the ball, made the Pirates his third team of the 2003 season, but departed once the season was over. Hill had an adequate 2004 for Pittsburgh, batting .266 over 126 games, while Bruback never cracked a big-league roster.

Ramirez was a two-time All-Star with the Cubs and won the 2008 National League Hank Aaron Award.

Mark Teixeira

8. Texas Rangers send Mark Teixeira to the Atlanta Braves for Elvis Andrus, Neftali Feliz, Matt Harrison, Beau Jones and Jarrod Saltalamacchia. – July 31, 2007

It was supposed to be the trade that pushed the Braves over the edge and into the playoffs, but instead, it helped set up the Rangers to head to the World Series in both 2010 and 2011. The trade came on the heels of Teixeira turning down an 8-year, $140 million contract extension, and he did play well for the Braves in 2007, batting .317 with 17 home runs in 54 games, but he only lasted a calendar year in Atlanta, as he was shipped to the Los Angeles Angels in July 2008.

The haul for the Rangers, however, was massive. They gained their everyday shortstop in Andrus, who was named to both the 2010 and 2012 All-Star teams. Feliz was named the 2010 Rookie of the Year, and Harrison was named to the 2012 All-Star team.

Fred McGriff

7. San Diego Padres send Fred McGriff to the Atlanta Braves for Donnie Elliott, Vince Moore and Melvin Nieves –  July 18, 1993

With the Padres scuffling towards a 101-loss season, they unloaded a then 29-year old Fred McGriff on the Braves for a trio of prospects. McGriff hit an important home run for Atlanta in his very first game, and helped lead the Braves to a 51-19 record over their final 70 games, which helped them capture the division title. He remained a key cog for Atlanta throughout their 1995 season, in which the Braves won Atlanta’s only World Series title. Nieves, Elliott and Moore never amounted to much at the major league level, and Padres fans would have been happy to have McGriff in 1998, when San Diego was swept in the World Series by the New York Yankees.

Ken Phelps

6. New York Yankees trade Jay Buhner to Seattle for Ken Phelps – July 21, 1988

I could post all about Buhner’s great career with the Mariners and how the Yankees would have loved to have the 307 home runs he hit with Seattle, but I’ll let Frank Costanza take it from here.

Heathcliff Slocumb

5. Seattle Mariners send Derek Lowe and Jason Varitek to the Boston Red Sox for Heathcliff Slocumb – July 31, 1997

The Mariners were looking to acquire a veteran bullpen arm and they got it in the then 31-year old Slocumb, who picked up 10 saves for Seattle over the course of the end of the 1997 season. The Mariners lost to Baltimore in the ALDS, and Slocumb would go on to play just one more season in Seattle. Lowe became an integral part of the Red Sox’ staff for the next eight seasons, going 21-8 in 2002. He also went 4-1 for Boston in the 2004 playoffs, picking up the final win for the Red Sox in Game 4 of the World Series. Varitek became Boston’s captain and spent 15 seasons in Beantown, playing a vital role behind the plate on both of the Red Sox’ title teams.

Bartolo Colon

4. Montreal Expos trade Cliff Lee, Brandon Phillips, Grady Sizemore, and Lee Stevens to the Cleveland Indians for Bartolo Colon and Tim Drew – June 27, 2002

Fresh off a last place finish in the NL East in 2001, the Expos were in contention into the summer months in 2002 and wanted to make a move for a talented young pitcher. Colon fit that bill, having averaged over 15 wins in his previous four seasons in Cleveland. It took a haul of prospects to bring in Colon, and unfortunately for Montreal, it was an impressive array of prospects that they had to part ways with. Not all of their awards were won with the Indians, but Sizemore, Lee and Phillips have combined for 10 All-Star game appearances, five Gold Gloves and a Cy Young award.

Larry Andersen

3. Boston Red Sox trade Jeff Bagwell to the Houston Astros for Larry Andersen – August 30, 1990

Just 15 months after drafting Bagwell, then a third-basemen for Boston’s Double-A affiliate, the Red Sox flipped him for Andersen, a veteran bullpen arm to help them out during their stretch run. Andersen would pitch a grand total of 22 innings for the Red Sox, while Bagwell built a Hall of Fame-caliber career in Houston. The 1994 MVP accumulated 2,314 hits for the Astros, retiring shortly after leading Houston to the 2005 World Series, where it ultimately came up short against the Chicago White Sox.

Doyle Alexander

2. Detroit Tigers send John Smoltz to the Atlanta Braves for Doyle Alexander – August 12, 1987

Alexander provided the Tigers exactly what they were looking for in 1987, winning nine of his 11 starts with a 1.53 ERA over 88 innings. Even that impressive season pales in comparison to what Smoltz ended up turning into with Atlanta. In addition to helping lead the Braves to the 1995 World Series crown, Smoltz racked up 210 wins, eight All-Star appearances and the 1996 Cy Young award. After an injury forced him to miss the 2000 season, Smoltz reinvented himself as a closer, saving 154 games over the course of four seasons. He combined with Greg Maddux and Tom Glavine to form one of the most formidable pitching trios in baseball history for Atlanta in the 1990s.

Ernie Broglio

1. Chicago Cubs trade Lou Brock, as well as Jack Spring and Paul Toth, to the St. Louis Cardinals for Ernie Broglio, Doug Clemens and Bobby Shantz – June 15, 1964

Trying to fill a hole in left field after Stan Musial retired in 1963, the Cardinals front office targeted Brock, who the Cubs were apparently ready to give up on. He was only a .260 hitter in Chicago, but he hit .348 for the Cardinals the rest of the way and helped to elevate St. Louis from eighth place in the National League to the NL pennant four months later. To put the icing on the cake, the Cardinals won the 1964 World Series in seven games over the New York Yankees. Brock went on to play in six All-Star games and he entered the Hall of Fame in 1985. Broglio’s pitching dropped off significantly in his tenure with the Cubs, winning just seven games for Chicago and he retired after the 1966 season.

About Chris Callaway

Chris lives and works in La Crosse, Wisconsin, working primarily on-air while doing some writing as well. He is a part-owner of the Green Bay Packers, a Milwaukee Brewers die-hard, learning hockey while supporting the Minnesota Wild, and is also a fan of the Wisconsin Badgers and the Notre Dame Fighting Irish. Follow him on twitter @ccallaway33.


  1. Can someone tell me how the Miguel Cabrera trade from Florida to Detroit did not make the list? Cabrera has gone on to be one of the top players in all of baseball (an argument can be made for THE top player). Whereas the people he was traded for…Andrew Miller was supposed to be a dominant up and comer pitcher but never did anything for Florida but has resurfaced for Boston. Cameron Maybin never turned in the superstar tht Al Kaline thought he would be. Lets not even address Dallas Trahern, Mike Rabelo, Eulogio De La Cruz or Burke Badenhop.

    • Chris Callaway says:

      That trade happened in December of 2007. I took a look at the worst trade-deadline deals of all-time. But you’re correct. That trade didn’t turn out as well as the Marlins would have hoped.

  2. Not only was Texiera traded in back-to-back Trade Deadlines, the pieces gotten back made and broke a franchise. The Texas deal brought back huge reward for both teams (more so Texas), but when the Braves traded him for Casey Kotchman, robbery was committed! Kotchman was horrible with the Braves, who lost a power bat in the middle of the lineup and fell to a brief stint of mediocrity for the next couple of years.

  3. the tigers trade in 87–was a great trade!!! not worst.without that trade the tigers wiould have never made the playoffs.alexander went like 12–0.

  4. I know you are only focus on Trades at the Trading dead night but what about New York Mets traded Nolan Ryan to the California Angels for 3B Jim Fregosi.

  5. How about the braves sending Adam wainwright for j d drew

  6. The worst trade in major league baseball was the trade the Boston Red Sox made when they traded Babe Ruth to the New York Yankees, bar none!!!

  7. Not a trade deadline deal, but Frank Robinson to Baltimore is still a head scratcher.

  8. What? No Glenn Davis from Houston to Baltimore for Curt Shilling, Pete Harnish, Center fielder (forgot gold glove outfielders name who later starred for the Angels), and cash! 1990 I believe or 91, Davis went to camp, had a fight, broke hand batted like .191 and never played!!!! WORST EVER esp for an O’s fan!
    Maybe not a trade deadline deal, but one of worst trades ever! (Barring Babe Ruth)

  9. How about me not being on the Royals’ roster? That has to be in there somewhere!!

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