MLB Power Rankings of the worst trade deadline deal every team has made in its history.
The MLB trade deadline should be a holiday. In fact, baseball fans should be allowed to take off from work, household chores, and any other responsibilities leading up to the big summer day. It's not always on the same exact date but it's always something to look forward to. In this week's MLB Power Rankings we'll look at some not-so-great moments for a couple of ball clubs around the trade deadline.
Nobody bats 1.000 with their trade deadline deals. These 30 trades have a clear winner and loser. It's the worst trade deadline move every MLB team has ever made.
30) MLB Power Rankings: Minnesota Twins, Scott Erickson to the Orioles
On July 7, 1995, the Minnesota Twins traded Scott Erickson to the Baltimore Orioles for Scott Klingbeck and Kimera Bartee. Erickson had an up-and-down career with the Twins, leading the league with 20 wins in 1991 and 19 losses in 1993. They shipped him out to the Orioles a little too early. His 5.95 ERA arrived in Baltimore and turned into a 3.89 ERA in 16 starts and a relief appearance. He'd actually stay with the Orioles for parts of 7 seasons. While he wasn't brilliant, Erickson had double-digit winning seasons often while surviving the Steroid Era while eating up a lot of innings. It's the best of the worst trade deadline deals made by any team. Kudos to the Twins.
29) MLB Power Rankings: Los Angeles Angels, Jean Segura for a Zack Greinke rental
Jean Segura has been traded a bunch of times in his career. The first happened on July 27, 2012 when he was sent by the Los Angeles Angels with two others to the Milwaukee Brewers for Zack Greinke. The mercenary pickup by the Angels wasn't the most effective move. Greinke made 13 starts and went 6-2 with a 3.53 ERA for them. He'd leave for the Los Angeles Dodgers in the offseason. The big mistake might have been not extending him as Greinke grew into a true ace as soon as he joined the Dodgers. The Angels didn't even make the postseason in 2012. Segura, meanwhile, was an All-Star in 2013. It's not a trade to lose sleep over yet the weakest for the Angels mostly because they let the headliner leave.
28) MLB Power Rankings: Colorado Rockies, Not getting more for Troy Tulowitzki
The Colorado Rockies have been pretty good at avoiding bad trade deadline deals. Their worst has to be not getting more for Troy Tulowitzki. It's a theme for many of the worst Rockies trades. Still very much in the prime of his career at the time, he was sent to the Toronto Blue Jays for Miguel Castro, Jeff Hoffman, Jose Reyes, and Jesus Tinoco. None of the four players they got from Toronto would do anything close to what Tulowitzki did. This turned out to be an unsatisfying deal for the Blue Jays, too. However, it doesn't make it any better for the Rockies who should have gotten a lot more.
27) MLB Power Rankings: Arizona Diamondbacks, Matt Mantei for Brad Penny
The Arizona Diamondbacks don't have enough of a history for a truly brutal trade deadline deal. Their worst was one they were able to benefit from. On July 8, 1999, Matt Mantei was traded to the Florida Marlins for Vladimir Nunez, Abraham Nunez, and Brad Penny. Mantei would go on to have a 4.04 ERA and 74 saves for the Diamondbacks through the 2004 season. Multiple injuries limited him with the worst of it coming in 2001 when he missed out on the World Series run. It's how Penny performed which makes this more of a win for the Marlins than the Diamondbacks. Penny would win 121 games in his career while most notably taking home a championship with the 2003 Marlins. His World Series against the New York Yankees made the trade completely worth it. He won both of his starts and pitched to a 2.19 ERA.
26) MLB Power Rankings: Los Angeles Dodgers, Paul Konerko to the Reds
It's not fair for the Los Angeles Dodgers to be this good at trade deadline deals. Looking through many of their worst trades, the one qualified to be a trade deadline deal that was the most awful happened on July 4, 1998. Paul Konerko and Dennys Reyes were traded to the Cincinnati Reds for Jeff Shaw. Shaw was a good closer addition for the Dodgers which is why this isn't such an unforgivable deal. He never did win a championship for them, though. And considering the 439 career home runs Konerko would hit, one has to wonder if maybe another prospect could've gotten the deal done.
25) MLB Power Rankings: Kansas City Royals, Stan Belinda for Jon Lieber and Dan Miceli
Finding the worst trade deadline deal in Kansas City Royals history was the most difficult for this list. Some were fairly obvious. This one wasn't. There were a few players the Royals traded away for a less than desirable haul. One instance cost them two young pitchers who would have productive careers. It was on July 31, 1993, when Stan Belinda was traded to the Royals from the Pittsburgh Pirates for Jon Lieber and Dan Miceli. They'd both end up being decent major leaguers for a long time. What made this deal bad for Kansas City was Belinda's performance. He had a 4.28 ERA in a non-closer role from the one he had in Pittsburgh. Returning in 1994, his ERA inflated up to 5.14. By the time he left, the Royals would enter a dark time in franchise history when trade deadline selling was much more the norm.
24) MLB Power Rankings: Cincinnati Reds, Johnny Cueto to the Royals
From the worst trade deadline deal for the Kansas City Royals to one of their best, the Cincinnati Reds didn't get nearly enough when they sent starting pitcher Johnny Cueto to the American League in 2015. The Royals were on their way to winning a World Series with Cueto being a major factor, at least in the postseason. Cueto was a pure rental for the Royals. It cost them Brandon Finnegan, John Lamb, and Cody Reed. None did much of anything in Cincinnati making this one of those deals where the buy was the biggest victor. Cueto came out pretty nicely in free agency, too.
23) MLB Power Rankings: San Diego Padres, Selling Corey Kluber too soon
Corey Kluber was sent from the San Diego Padres to the Cleveland Indians on July 31, 2010, as part of a three-team deal with the St. Louis Cardinals also involved. The Padres picked up Ryan Ludwick in the move. It cost them much more than they realized. Kluber would go on to win two Cy Young awards for Cleveland in the coming years while helping to reshape their franchise. They even managed to trade him years later for Emmanuel Clase. In parts of two seasons with the Padres, Ludwick batted only .228/.301/.358.
22) MLB Power Rankings: Pittsburgh Pirates, Aramis Ramirez to the Cubs
Any trade between division rivals has a lot more riding on it. On July 23, 2003, the Pittsburgh Pirates and Chicago Cubs agreed to a deal that would come back to haunt the former. Aramis Ramirez, Kenny Lofton, and cash were all sent to the Cubs for a weak haul of Matt Bruback, Jose Hernandez, and Bobby Hill. Ramirez was a growing power threat in Pittsburgh. He became an absolute beast in Chicago. He'd play a total of 1124 games for the Cubs while clobbering 239 home runs. Hernandez was already nearing the end of his career while Bruback never made the majors and Hill barely played much at all.
21) MLB Power Rankings: Baltimore Orioles, Jake Arrieta to the Cubs
We have another trade deadline steal by the Chicago Cubs. This time their victim happened to be the Baltimore Orioles. On July 2, 2013, Jake Arrieta, Pedro Strop, and cash were all sent to the Cubs for Steve Clevenger and Scott Feldman. It almost sounds like a ridiculous trade in retrospect. Who knew Arrieta would suddenly become a star and win the 2015 National League Cy Young while also helping the Cubs to win the 2016 World Series? Feldman, the big "get" for the Orioles in this move made 15 starts for them and pitched to a 4.27 ERA in 2013. He'd leave for the Houston Astros in free agency several months later.
20) MLB Power Rankings: Chicago Cubs, Josh Donaldson and more for Rich Harden
The Chicago Cubs haven't been perfect at the trade deadline. In this instance, they were the big losers. This trade took place prior to the 2008 deadline. Sean Gallagher, Matt Murton, Eric Patterson, and Josh Donaldson were sent to the Oakland Athletics for Chad Gaudin and Rich Harden. The obvious name that stands out is Donaldson. He'd become a star with the Athletics and later with several other teams. If not for his inclusion, this wouldn't be such an awful trade. Gaudin didn't help either with his 6.26 ERA. Harden was elite for the Cubs in 2008, going 5-1 with a 1.77 ERA in 12 starts. Unfortunately, he got rocked by the Los Angeles Dodgers in his one postseason start.
19) MLB Power Rankings: Atlanta Braves, The acquisition of Hector Olivera from the Dodgers
The July 30, 2015, trade between the Los Angeles Dodgers, Miami Marlins, and Atlanta Braves had a lot of moving parts. A total of 13 players were moved. Two of the biggest pieces involved were pitcher Alex Wood going to the Dodgers and Hector Olivera going to the Braves. Wood struggled in 2015 but was a quality arm for the Dodgers for a pair of seasons later on with his fantastic 2017 campaign standing out most. More notably was how poorly Olivera performed for the Braves. He played in just 30 games for them combined in 2015 and 2016. So fed up with his performance, he was dealt the following summer to the San Diego Padres for Matt Kemp and cash.
18) MLB Power Rankings: Tampa Bay Rays, Nelson Cruz rental for Joe Ryan
The Tampa Bay Rays are known for winning trades. They're smart. They're savvy. They also made a recent blunder at the trade deadline when they rented Nelson Cruz for a couple of weeks. Looking for some pop in 2021, they picked up Cruz from the Minnesota Twins. Calvin Faucher joined him in exchange for Drew Strotman and Joe Ryan. Ryan is well on his way to becoming an ace for the Twins if he's not already. He's the kind of pitcher the Rays would love to have. This one could age much worse as time goes on. After all, Cruz batted only .226/.283/.442 for the Rays in 238 plate appearances.
17) MLB Power Rankings: Miami Marlins, The Andrew Cashner overpay
The 2016 Miami Marlins trade for Andrew Cashner was a complete overpay. Cashner, Tayron Guerrero, and Colin Rea all went from the San Diego Padres to the Marlins for Carter Capps, Luis Castillo, Jarred Cosart, and Josh Naylor. Cashner wasn't very good at all for the Marlins, pitching to a 5.98 ERA and winning only one game for them in 2016. The biggest loss for the Marlins in this trade was giving up Castillo who'd become a successful big league pitcher for the Cincinnati Reds later on and now with the Seattle Mariners.
16) MLB Power Rankings: Cleveland Guardians/Indians, Richie Sexson to the Brewers
Richie Sexson was one of those players for the Cleveland Indians who looked like he'd become a star slugger. Finding playing time wasn't always the easiest thing. This was one of the reasons why Cleveland traded him to the Milwaukee Brewers in the summer of 2000. Sexson would smack over 300 career home runs and reach the 45 mark twice with the Brewers. The trade itself was a massive one with reliever Bob Wickman being the biggest grab for Cleveland in the trade. They needed much more than him, though. Despite some very good years in Cleveland, Wickman would only ever toss one postseason inning. They should have kept Sexson or traded him in a more impactful deal.
15) MLB Power Rankings: Chicago White Sox, James Shields for Fernando Tatis Jr.
Who saw this becoming one of those most horrific trades in MLB history? In defense of the Chicago White Sox, Fernando Tatis Jr. has had his share of issues with a PED suspension at the top of the list. This was a trade taking place on June 4, 2016, when James Shields was sent to the White Sox for Erik Johnson and Tatis Jr. Shields' performance drove him out of baseball. He was 16-35 with a 5.31 ERA in Chicago. The full tale of what Tatis Jr. can accomplish has yet to be written, but failures of Shields make this an inexcusable deal for the White Sox and their worst move at the trade deadline.
14) MLB Power Rankings: Milwaukee Brewers, Nelson Cruz and Carlos Lee to the Rangers
The second appearance by Nelson Cruz on this list is a shame on the Milwaukee Brewers who on July 28, 2006, sent him and Carlos Lee to the Texas Rangers. All they got back was a lifetime minor leaguer, Francisco Cordero, Kevin Mench, and Laynce Nix. Cruz was a young player at the time but later became one of the game's best sluggers by the 2009 campaign. His inclusion in this deal is what pushes it over the edge from a bad one to an absolutely ugly trade. Lee's time with the Rangers was much shorter yet memorable. He batted .322/.369/.525 with 9 home runs in 260 plate appearances down the stretch for the Rangers in 2006. The Brewers guessed wrong on the players they thought would make this a reasonable trade.
13) MLB Power Rankings: New York Yankees, Jay Buhner for Ken Phelps
A trade so bad it was immortalized on Seinfeld, the New York Yankees sent two lifelong minor leaguers and Jay Buhner to the Seattle Mariners for Ken Phelps. Buhner would spend the rest of his career with the Mariners and from 1995-1997 he hit 40+ home runs and drove in over 100. As for Phelps, he hit .224/.339/.551 for the Yankees in his first 127 plate appearances in 1988. He wasn't much better in 1989. The Yankees ended up trading him in August to the Oakland Athletics for a guy who never reached the big leagues. In the middle of a rare Yankees drought where championships were impossible to find, this trade helps define the ineptitude.
12) MLB Power Rankings: Houston Astros, Ben Zobrist for Aubrey Huff
This was a low-key bad trade deadline deal that probably doesn't get enough attention. The 2006 trade deadline included the Houston Astros acquiring Aubrey Huff from the Tampa Bay Devil Rays for Mitch Talbot and Ben Zobrist. Huff hit .250/.341/.478 with 13 home runs for the Astros. It wasn't bad at all, but he did leave in free agency the next season. Zobrist's contributions to Tampa Bay were much bigger, though. One of the most important players in the franchise's young history, he helped revitalize the importance of the everyday utility player. The Astros chose wrong by including him in their deal for Huff.
11) MLB Power Rankings: San Francisco Giants, George Foster to the Reds
A young George Foster was traded by the San Francisco Giants to the Cincinnati Reds on May 29, 1971. Frank Duffy and Vern Geishert were the two players the Giants got back. It took Foster a while to get going but when he did, Foster became one of the best sluggers in baseball. He led the league in home runs twice and RBI three times. Duffy played 21 games for the Giants and Geishert had only 11 MLB games in his entire career. All of them came before this trade even happened.
10) MLB Power Rankings: Washington Nationals/Montreal Expos, Randy Johnson for Mark Langston
Because the Washington Nationals are so young, we need to go back to their days in Canada as the Montreal Expos to find a truly abominable trade deadline move. It was on May 25, 1989, when they acquired Mark Langston and Mike Campbell from the Seattle Mariners for three players. One of them was Randy Johnson. During a time when the trade deadline was on June 15, the Expos were making an early grab to help themselves out. Langston would go 12-9 with a 2.39 ERA for the Expos. He'd leave in free agency while Randy Johnson got his chance for the Mariners. In 1990, Johnson was an All-Star for the first time. Still very wild in those early days, those were the beginning stages of a Hall of Fame career for the man we know as The Big Unit.
9) MLB Power Rankings: Philadelphia Phillies, Curt Schilling to the Diamondbacks
Teams never learned. Every time Curt Schilling is traded, the team that gave him up loses. The Philadelphia Phillies knew a lot about losing in the 1990s. Even with Schilling on their roster, they were frequently at the bottom of the National League. It was in the middle of the 2000 season when they finally dealt him to the Arizona Diamondbacks. He helped them win the World Series the very next year and would do the same for the Boston Red Sox in 2004. In return for Schilling, the Phillies received Omar Daal, Nelson Figueroa, Travis Lee, and Vicente Padilla. Average players at best, quantity did not beat quality in this deal.
8) MLB Power Rankings: Seattle Mariners, Derek Lowe and Jason Varitek to the Red Sox
July 31, 1997, was an important day in Boston Red Sox history. It was a dreadful one for the Seattle Mariners. A team that has yet to even make it to the World Series acquired a very mediocre pitcher, Heathcliff Slocumb, in exchange for two of the core members of the 2004 Red Sox championship. Slocumb had a 4.13 ERA in 28.1 innings in 1997 and saw it rise to 5.32 in 1998. The Mariners gave up Derek Lowe and Jason Varitek for him. Lowe had plenty of good years for the Red Sox but most importantly he was a postseason hero and the winner of the World Series clincher in 2004. Varitek became the team captain and there isn't a single moment or season to truly define his importance to the Red Sox. All of this was given up for a bad reliever.
7) MLB Power Rankings: Toronto Blue Jays, David Cone to the Yankees
Major points are deducted for this trade because of the teams involved. On July 28, 1995, the Toronto Blue Jays made their worst trade deadline deal. David Cone was sent to the New York Yankees for Marty Janzen and two players who never made the majors. While Cone was just a rental, playing for the Yankees in 1995 reunited him with the Big Apple and helped lead to multiple new contracts with them. Cone was a big part of the late 1990s success for the Yankees. Despite being into his mid-30s already, he'd go 81-51 with a 3.13 ERA over parts of seven seasons. The Blue Jays fed him to a rival and officially handed over the American League East to a rival.
6) MLB Power Rankings: Texas Rangers, Sammy Sosa for Harold Baines
This may be an outlier of bad trade deadline deals for a strange reason. That's because the team with the Hall of Famer looks like the loser. It was on July 29, 1989 when Wilson Alvarez, Scott Fletcher, and Sammy Sosa were all sent from the Texas Rangers to the Chicago White Sox for Harold Baines and Fred Manrique. Alvarez had a pretty good career with the White Sox, however, it's Sosa who trumped this trade. Of course, the Rangers ruined their good fortune by later trading Sosa to the Chicago Cubs before he took off. Baines was just okay for the Rangers and ended up traded to the Oakland Athletics a little over a year later in a deal nobody probably remembers.
5) MLB Power Rankings: Oakland Athletics, Mark McGwire to the Cardinals
Back-to-back 1998 home run breakers. Our inner children love this. It was on July 31, 1997, when the St. Louis Cardinals were the winners in the worst trade deadline deal the Oakland Athletics have ever made. They sent slugger Mark McGwire to the St. Louis Cardinals for Eric Ludwick, T.J. Mathews, and Blake Stein. None were all that good in Oakland or anywhere else after. McGwire had already shown he was capable of setting home run records and in his first full season with the Cardinals he swatted 70 of them. Although his reputation may have become tarnished due to the use of steroids, this was a sweet move by the Cardinals and a sour one by the Athletics. They got little in return for a mammoth.
4) MLB Power Rankings: Detroit Tigers, John Smoltz for Doyle Alexander
This is one of those trades where a team gave up a lot and actually got a decent performance out of it. At the 1987 trade deadline, the Detroit Tigers acquired Doyle Alexander from the Atlanta Braves. He'd go on to finish the year 9-0 with a 1.53 ERA in 11 starts. It was everything they could've asked for except Alexander ended up losing both of his postseason starts while getting rocked for 10 earned runs in 9 innings of work. He wasn't very good his next two seasons with them. The price was high. It cost them a young pitcher named John Smoltz. What's there to say about Smoltz other than he became one of the greatest pitchers in the game? This trade would have a different story if the Tigers won the 1987 World Series. They didn't so it remains a stinker.
3) MLB Power Rankings: New York Mets, Tom Seaver to the Reds
Arguably the worst trade the New York Mets have ever made with only the Nolan Ryan deal coming close to it, the 1977 Midnight Massacre deal is what lands them so high in these MLB Power Rankings. Mets management was cheap and unwilling to pay its star pitcher or many other players a reasonable salary. At the 1977 trade deadline, Seaver was sent to the Cincinnati Reds for four players. Some of them were okay but not nearly as impactful as Seaver. For someone who helped define a franchise for a decade, it was a sad and unnecessary ending due to frugality.
2) MLB Power Rankings: St. Louis Cardinals, Keith Hernandez to the Mets
Years after making their worst trade deadline move, the New York Mets got some vengeance by acquiring Keith Hernandez from the St. Louis Cardinals. Hernandez was still in the prime of his career but off-field issues led the Cardinals to send him to the Mets in the summer of 1983. Hernandez was the MVP runner-up the very next season and would go on to win multiple Gold Gloves with the Mets. In 1986, he helped lead them to a championship. The Cardinals would go on to lose the 1985 World Series only to see their former star win a season later. All they got in return for him were Neil Allen and Rick Ownbey.
1) MLB Power Rankings: Boston Red Sox, Jeff Bagwell for Larry Andersen
The worst of the worst. Number one in this week's MLB Power Rankings and perhaps forever stuck in evergreen status as the worst trade deadline deal in the history of the sport is an honor belonging to the Boston Red Sox. Most well-known for trading Babe Ruth to the rival New York Yankees, their 1990 trade deadline deal for relief pitcher Larry Andersen is at the bottom of all teams for trade deadline moves. That's because for just 22 innings of relief work, they gave up future Hall of Famer Jeff Bagwell. The Houston Astros snatched up a star while the Red Sox acquired a guy who pitched well in the regular season but lost Game One in the ALCS. They'd go on to get swept away by the Oakland Athletics in their one playoff series. Andersen left for free agency in the offseason. Bagwell won the Rookie of the Year the very next season. Maybe the Red Sox could've won sooner than 2004 if they hadn't made this move.
