The AL East Division is among the most competitive in all of baseball. The key reason is simple; it has the Yankees and the Red Sox. For a century, these two rivals have been going head to head for supremacy in the AL and that’s continued even as baseball has broken up into various divisions and wild cards. There’s also the Baltimore Orioles, a team who sadly are bad but have a history of multiple championships as well. The Toronto Blue Jays represent Canada while the Tampa Bay Rays provide some excitement at times. Thus, you have a long history of teams who are always fighting it out for a crown and often find themselves clashing when the time to decide the AL comes about.
With all that history, it’s no surprise that each team has made moves over the years to try and give themselves an edge with players. And as is so often in baseball, several of these moves backfire big time, especially trades. Each team knows what it’s like to try and get a good player only to end up with a dud. Worse is trading away a future star in exchange for nothing. Some of these deals have become baseball lore and topping almost any other team in terms of terrible trades to show how notable this division is. Here are the 5 worst trades of every team in the AL East to show its power in baseball.
25 Baltimore Orioles: Frank Robinson To LA For Doyle Alexander, Bob O'Brien, Sergio Robles and Royle Stillman
In 1965, the Reds traded Frank Robinson to the Orioles on the idea that he was “an old 30.” Robinson responded by spending his first year with the team winning the Triple Crown, named MVP and leading Baltimore to their first World championship. Robinson was the star of the team, leading them to three more AL Pennants and another World title. So it was jarring in 1971 when Baltimore traded Robinson to the Dodgers for Doyle Alexander, Bob O'Brien, Sergio Robles and Royle Stillman.
While Baltimore was strong, none of those players made much of an impact. Thus, keeping Robinson could have kept Baltimore back in winning a couple more AL Pennants and maybe another championship. Maybe it makes sense the guy involved in their best trade was also among their worst.
24 Boston Red Sox: Fred Lynn To The Angels
Fred Lynn was a true favorite of 1970s Red Sox fans. He was the 1975 MVP and Rookie of the Year as well as the 1979 AL batting champion. A good player and very popular, it looked like Lynn would be a Boston favorite for a while. However, in early 1981, Lynn was part of a multi-player trade to the Angels and Boston fans were irate.
Lynn continued with a long All-Star career, including MVP of the 1982 ALCS. Keeping him in Boston would have helped the Red Sox a lot in the ‘80s but instead they traded off a guy who could have put them in better contention.
23 New York Yankees: Mark Melancon & Jed Lowrie For Lance Berkman
A late addition to the list, Mark Melancon was drafted by the Yankees in 2006 and made his debut three years later. While he has a ring as part of that squad, he was actually sent back to the minors for more training. He and Jed Lowrie were then traded to the Astros for Lance Berkman whose New York tenure would be short-lived.
Melancon had a good stint with the Astros and since moved around the league.
He hit his height in 2015 with the Pirates, leading the NL in saves and was the best reliever of the season.
A three-time All-Star, he’s now with the Giants and a great pitcher New York gave up for nothing.
22 Tampa Bay Rays: Bobby Abreu For Kevin Stocker
During the 1997 expansion draft, the Rays managed to get their hands on Bobby Abreu, who had been showing promise with the Astros. Just hours later, they dealt him to the Phillies for shortstop Kevin Stocker. Stocker’s career would be nothing notable, two seasons of so-so play before being released. Meanwhile, Abreu would make his mark as a power hitter, a two-time All-Star and Golden Glove winner. He would boost up the Phillies while also playing for the Yankees, Angels, Dodgers and Mets and a major miss for the Rays.
21 Toronto Blue Jays: Dave Cone
Now, this is interesting. After time as a good pitcher in Kansas City and the Mets, Dave Cone was traded to the Blue Jays in 1992 in time to win the World Series. He then entered free agency to return to the Royals and win the Cy Young award. After the strike in 1995, Kansas City traded Cone back to Toronto as a part of a big deal. But just weeks later, Toronto sent Cone over to the Yankees for Marty Janzen, Jason Jarvis and Mike Gordon. Cone blossomed in New York, leading the AL in wins in 1998, throwing a perfect game in 1999 and won four World Series. In other words, Toronto twice had this guy and let him go.
20 Baltimore Orioles: Trading For Sammy Sosa
Many a team has been conned into trading for a guy past his prime, not getting how he’s on the downslide of a career. Baltimore fell into that trap in 2005. They saw Sammy Sosa and figured he was still the guy slamming massive home runs every season and a top fielder.
The Cubs knew Sosa was on the downside and thus got Baltimore to give up outfielder Jerry Hairston, Jr., infielder Mike Fontenot, and RHP Dave Crouthers.
Sosa proceeded to have the worst season of his career in 2005, .221 with 14 home runs. ’06 was even worse so the Orioles cut him loose and groused over spending so much on an overpriced veteran.
19 Boston Red Sox: Sparky Lyle To The Yankees
Rising up in 1967, Sparky Lyle was making a name for himself as a serious closer. He had a good arm and instincts and seemed ready for more from the Red Sox. However, they decided to trade him to the Yankees at the start of the 1972 season for Danny Carter and a player to be named later. It didn’t take long for Boston to regret it as Lyle became a Cy Young winner and one of the most dependable closers in the game. He won two World Series with the Yankees and co-wrote the classic book “The Bronx Zoo” to drive Red Sox fans crazy they gave this guy to their rivals.
18 New York Yankees: Mike Lowell To The Marlins For Mark Johnson and Ed Yarnall
While he technically has three rings, Mike Lowell didn’t do too much to earn the first one. He was called up by the Yankees in 1998 but used sparingly so while he was part of that championship team, he didn’t contribute much. The Yankees must have figured it was better to unload him and in 1999 traded Lowell to the Marlins for Mark Johnson and Ed Yarnall. In 2003, Lowell’s hitting was a key reason for the Marilns’ success as they beat the Yankees in the World Series. The Marlins traded him to Boston where Lowell had a fantastic 2007 culminating in winning another World Series. In other words, the Yankees traded a guy who ended up getting two rings off them in the future.
17 Tampa Bay Rays: Dealing Wil Myers
Originally drafted by the Royals, Wil Myers was traded to Tampa Bay before breaking out. In 2013, he burst out majorly, winning Rookie of the Year honors despite only being in 100 games.
Despite injury in 2014, the promise of Myers becoming a major star was right there.
It was stunning that Tampa Bay made him part of a big three-team trade with the Padres and Nationals that sent Myers to San Diego. While he’s had issues, Myers is also an All-Star with great power hitting and base-stealing and the young talent Tampa Bay could have done a lot more with.
16 Toronto Blue Jays: Acquiring Ben Revere
After showing his stuff (including being the NL hits leader in 2014) with the Phillies, Ben Revere seemed a top star in the making. Toronto agreed and traded Alberto Tirado and Jimmy Cordero to get Revere. For a time, it looked like it was working out with Revere doing some great hitting. But then came the infamous blow-up in the 2015 ALCS where, after striking out, Revere beat up a trash can in frustration after a bad postseason play. The Blue Jays thus traded him off to Washington, showing all they got out of the deal was one very ugly public moment.
15 Baltimore Orioles: Selling Off Manny Machado
True, this deal is pretty recent yet it’s already looking pretty bad. In just a few seasons, Manny Machado has been a great start for Baltimore, a four-time All-Star, very popular and a two-time Golden Glove winner. True, he’s had issues with management and an infamous tirade but still a great hitter, finishing 2017 on a strong note. Still, Baltimore decided to ship him off to the Dodgers for Yusniel Diaz, Dean Kremer, Rylan Bannon, Breyvic Valera and Zach Pop.
Giving up so much for one guy may be a risk for the Dodgers but it’s also a bit jarring for Baltimore to give away a top player and it may backfire on them down the road.
14 Boston Red Sox: Jon Lester & Jonny Gomes To Oakland For Yoenis Cespedes
Sure, the Red Sox have gotten three World titles in the last decade and a half. But they still make some bad mistakes and this was a doozy.
Lester was already a great pitcher who had won two World Series for Boston and was still in his prime.
Yet Boston seemed to think it was better to look for the future so traded Lester and Jonny Gomes to the A’s for Yoenis Cespedes and a future pick. Lester had a brief time in Oakland before going to Chicago, helping the Cubs win the World Series and remaining one of the best pitchers out there. It has to rankle Boston they could have had more of Lester for a while.
13 New York Yankees: Fred McGriff To Toronto
Born in Tampa, Fred McGriff was signed by the Yankees in the 1981 draft with a $20,000 bonus. But just the next year, he was dealt to Toronto as part of a multi-player trade. While the other players involved are forgettable, McGriff soon became a fantastic player. He was a five-time All-Star and twice led the league in home runs.
Perhaps the only reason he’s not in the Hall of Fame is that he played for seven teams across his career. But each time, he was good with the highlight being winning the 1995 World Series with the Braves. That long career could have been New York’s and maybe McGriff would be in the Hall had he stayed.
12 Tampa Bay Rays: Corey Dickerson To Pittsburgh
This is pretty recent but it has to count. Already a good player for the Rockies, Dickerson was made part of a multi-player trade to bring him to Tampa Bay in 2016. At first, it looked like a bad deal as his play as a Ray was poor compared to Colorado. But in 2017, Dickerson rebounded big-time as an All-Star and great numbers. He leveled off at the end of the season but the potential still there.
Instead, Tampa Bay traded him in early 2018 to the Pirates for three players. Dickerson has been doing well in Pittsburgh and with all his potential, it seems foolish for Tampa Bay to give him up so fast.
11 Toronto Blue Jays: Vernon Wells To Angels For Mike Napoli
This trade was questionable at the time but no question it was a bad idea now. Mike Napoli had been showing serious promise with the Angels, including becoming their all-time home run leader.
In 2011, the Blue Jays traded Vernon Wells to get Napoli. Just four days later, they traded him to the Rangers for pitcher Frank Francisco.
Francisco had just one year in Toronto before moving on. Meanwhile, Napoli became a prime hitter for the Rangers then joined the Red Sox in time to win the 2013 World Series. He was part of the Indians’ 2016 World Series run before making a return to the Rangers to show Toronto what they missed.
10 Baltimore Orioles: Jake Arrieta & Pedro Strop For Scott Feldman & Steve Clevenger
Despite about Jake Arrieta and Pedro Strop had been showing real promise for the Orioles, Baltimore had an eye on better talent. So they pulled off a 2013 deal with the Cubs to ship those two off for Scott Feldman and Steve Clevenger. Feldman lasted one year before heading to Houston while Levenger likewise made no impact. Meanwhile, Arrieta and Strop became part of the Cubs team that won the 2016 World Series, making this a truly idiotic deal in hindsight.
9 Boston Red Sox: Jeff Bagwell To HOU For Larry Anderson
Houston fans should give the Red Sox a thank you note. Jeff Bagwell was drafted by the Sox in 1989 and looked very promising. But Boston didn’t think he was worth that much and sent Bagwell to Houston in exchange for Larry Andersen. Andersen’s work in Boston would be only so-so and nothing special after 1990. Bagwell, meanwhile, became the most popular player in Astros history, the 1991 Rookie of the Year, 1994 MVP and is in the Hall of Fame. Talk about a bad deal for Boston although still nothing compared to their worst trade ever.
8 New York Yankees: Jay Buhner To Seattle For Ken Phelps
This was a trade so epic even Seinfeld made fun of it. Jay Buhner was rising in New York in the late 1980s, a time when the Yankees were pretty bad. In 1988, he was traded to Seattle in exchange for Ken Phelps.
Once in Seattle, Buhner blossomed into a fantastic hitter, powering the Mariners into contention and smashing numerous homers and RBIs.
He also inspired a fan fave “buzz cut” that became popular across the league. Seattle fans love to needle the Yankees for this bad move.
7 Tampa Bay Rays: Randy Winn To Seattle For Lou Pinella
One of the first players for the expansion Rays, Randy Winn showed his stuff as a serious hitter and a representative of the team off the field.
In 2002, the team made him part of a trade to Seattle in exchange for Lou Piniella being made manager.
He was good there but much better in San Francisco as a powerful hitter while the Rays sunk under Pinella. Keeping Winn could have kept Tampa Bay in better contention and at least helped them out more with fans.
6 Toronto Blue Jays: Selling The Farm For R.A. Dickey
The Blue Jays must have thought they were getting a good deal here. R.A. Dickey had shown his skills as a pitcher in New York, a Cy Young winner who led the NL in strikeouts in 2012. Thus, Toronto opened up, trading Travis d'Arnaud, John Buck, Noah Syndergaard and Wuilmer Becerra to get him. That Dickey was pushing 40 should have been a warning sign yet few could imagine his arm fading badly once he got to Canada.
While he was okay in 2013, he was far worse the next year with 14-13 and 3.71 ERA. By the time Toronto unloaded him in 2016, it was clear Toronto had wasted promising players for a guy already over the hill.
5 Baltimore Orioles: Trading Curt Schilling, Pete Harnish & Steve Finley For Glenn Davis
It’s still one of the worst deals in Orioles history. Maybe in the history of so many teams. In 1991, they became convinced Glenn Davis was a future superstar and willing to give anything for him. That included handing off Curt Schilling, Pete Harnisch and Steve Finley to get Davis. What they got was a guy who hit just 24 homers in three injury-plagued seasons before fading out. Meanwhile, of those three given away, the biggest was Schilling who became the 2004 World Series hero for Boston and one of the best pitchers of his time. No wonder Baltimore fans grouse at the mention of Davis’ name.
4 Boston Red Sox: Babe Ruth
What else could it be? To this day, nothing rankles Red Sox fans than this.
In the late 1910s, Boston was rising up as a serious force in the AL thanks to Babe Ruth.
He was already establishing himself as a huge star. But then owner Harry Frazee, needing money to pay off debts, sold Ruth off to the Yankees. Thus began the Yankees dynasty and 86 years of agony for Red Sox fans. Maybe more of a sale but it also counts as a trade in those days and has to top the list.
3 New York Yankees: Willie McGee To St. Louis For Bob Sykes
One of the single dumbest moves of the Yankees in the 1980s was this. Thinking they were getting a prime pitcher, the Yankees moved for a trade with the Cardinals for pitcher Bob Sykes. Sykes’ career would be forgettable to say the least. To get him, New York sent St. Louis Willie McGee, a young outfielder. McGee soon became one of the most popular players in Cardinals history. A four-time All-Star, he was part of the Cardinals’ 1982 World Champions team and the 1985 NL MVP. He played for other teams but McGee is tied to St. Louis and highlights how horrible this trade was for New York.
2 Tampa Bay Rays: Rolando Arrojo To COL
When the Devil Rays were formed, it soon became clear that Rolando Arrojo was the star. A sensation in Cuba who had won a gold medal, Arrojo defected to the U.S. in 1996. His work with Tampa Bay made him the team’s first All-Star and most popular player with fans. In 1999, with concerns his arm was deteriorating, Arrojo was traded to Colorado for Vinny Castilla. Vinny would barely make any impact in Tampa while Arrojo continued to do well for a few more seasons. Giving away their biggest star has to rank as the worst trade in Rays history.
1 Toronto Blue Jays: Roy Halladay To Philly For Travis d'Arnaud, Kyle Drabek & Michael Taylor
Nothing outrages a Toronto fan like this. In 1995, the Blue Jays landed Roy Halladay in the draft. He was soon breaking out as a Cy Young winner and All-Star, a fantastic pitcher and highly popular in Toronto. That was why the city was outraged in 2009 when the Blue Jays traded Halladay to the Phillies for Travis d'Arnaud, Kyle Drabek, and Michael Taylor. None of those three would make any sort of impact for Toronto.
Meanwhile, Hallady continued his great work which included a perfect game and a post-season no-hitter as well as another Cy Young award. Toronto fans still throw their hands up on this deal.