One move is all it takes to transform a baseball team. One trade and you can end up with a future star, the missing ingredient needed to boost your team up and make it into a group of champions. Another trade and you give away a star and saddled with a bust that sinks you badly. You can be given a chance to sign a major talent or let one slip through your grasp. Every team in history has faced that chance, some more than others. A few are lucky to make the moves and bring in the stars that make them into legends. Others, however, make a move that ends up causing nothing short of utter disaster. It’s tricky as so many times a deal that looks great on paper flops and leaves a general manager or owner with serious egg on their face.
It’s tricky going through the history of baseball and seeing so many of these deals. Some are legendary in how they represented the loss of a major future star and a move that hampered a team badly. Others are just astounding in how stupid they were and “what were they thinking?!” making these deals. A few times, it’s more games lost but it’s more fun to examine the times a future star slipped through the fingers or a bad decision was made that became worse in hindsight.
30 Arizona Diamondbacks: The 2009 Draft
Any team in baseball would kill to have a good first round pick. In 2009, the Diamondbacks pulled off the feat of having five. Five first round picks, you’d think nothing but sheer odds would indicate at least one of those would be a significant contributor for the team and could've resurrected the Diamondbacks as a National League contender. Instead, AJ Pollack has endured a series of injuries that marred his career. Chris Owings wasn’t much better while Bobby Borchering, Matt Davidson and Mike Belifore all ended up sinking fast. Combined, the latter three only played a total of 57 games for the Diamondbacks, a total waste of potential. They did land Paul Goldschmidt in the 8th round but failed to surround him with talent.
In other words, with five chances, the Diamondbacks totally missed on Mike Trout, easily the star of that draft year.
That’s not mentioning All-Star pitcher Shelby Miller who was also a better choice than anyone else the Diamondbacks tried to put in as a pitcher. The Diamondbacks have made just two postseason appearances since this draft and showcasing how a team can be given a golden opportunity and still blow it. This has gotta sting.
29 Atlanta Braves: Losing Tom Seaver
Maybe it wasn't totally their fault but it still has to rank as a huge mistake. Tom Seaver had been showing his skills in college, a fantastic pitcher with a record fastball. The Dodgers had the first crack at him but passed when Seaver demanded $70,000. In 1966, the Braves drafted Seaver and he signed a contract, ready to go. However, the Braves had missed that Seaver’s college team had played two exhibition games that year and thus the contract was voided. A huge mess was kicked up as Seaver hadn’t actually played in either of those games. Then-commissioner William Eckert said that any team that could match the Braves’ offer could vie for him.
The Braves threw a fit over not being allowed to take part in this but bound by Eckhert’s edict. The Mets, Phillies and Indians all made offers and the Mets were chosen literally out of a hat. Once in New York, Seaver became “The Franchise,” a 12-time All Star and 3-time Cy Young Winner. Thanks to him, the Mets went from the joke of baseball to World Champions in just three years. Meanwhile, Atlanta could only watch and grouse over what they could have had.
28 Baltimore Orioles: The Glenn Davis trade
In the annals of baseball, few things can cripple a team more than a bad trade. Baltimore learned this the hard way. In 1991, the team was trying to recover after some terrible years and thought the answer was in Glenn Davis. The Houston Astro star was a two-time All-Star and known for his power hitting. The Orioles thought he would provide firepower for them, the fantastic hitter and fielder they needed. But someone failed to do the scouting to see that Davis was slowed by injuries and on the downside of his career. Ignoring that, Baltimore traded Curt Schilling, Pete Harnisch and Steve Finley for Davis.
What they did get for that and a $3 million contract? Davis injured his neck in training and was never the same. It was worse the next year when he got his jaw broken in a bar fight and was let go after a fight over his starting position. Meanwhile, all three of those players would go on for All-Star careers. Finley would have 300 home runs and 300 stolen bases, an exclusive club. Schilling, meanwhile, would become part of the latter-day Red Sox dynasty that won three World Series and a lock for the Hall of Fame. It’s hard to find a trade more lopsided than this to add to the O’s woes.
27 Boston Red Sox: Selling Babe Ruth
What else could it be? When you make a move so bad that it begins an 86-year old “Curse,” you know it’s a huge deal. In the 1910s, the Boston Red Sox were a true powerhouse with several World Series wins. But owners Harry Frazee was in need of cash after bad deals and backing some Broadway flops. Thus, in the move that made his name a curse in Boston to this day, Frazee sold Babe Ruth to the Yankees for $100,000. For him to give away the man everyone easily recognized as the best player of his time was utterly ludicrous, but Frazee was more interested in the short-term of the money than the long-term success.
The fact Ruth had been demanding more and more cash was another factor as the duo had a rough relationship.
The deal was made and thus Ruth went to New York and created the Yankees dynasty.
Meanwhile, it wouldn’t be until 2004 that the Red Sox finally exercised the demons by winning the World Series. They’ve won two more since and laid a lot of this agony to rest. Yet, it still grouses Bostonians how one mistake turned them into a joke and gave birth to the dominance of their hated enemies.
26 Chicago Cubs: Trading Lou Brock
In 2016, the Cubs finally won the World Series and silenced the century-old “Curse” upon them. The origins of it are argued but it all comes down to the Cubs making a lot of bad moves over the years. One of the worst had to be in 1964 when the Cubs made what many still consider possibly the single worst trade in baseball history. Thinking they needed to beef things up, the Cubs sought to acquire pitcher Ernie Broglio from the Cardinals. In return, they made a multi-player deal that involved sending to St. Louis a young outfielder by the name of Lou Brock. Broglio turned out to be suffering from injuries and was soon out of baseball after just a handful of games.
Once in St. Louis, Brock turned into one of the best players in the game. With his hard hitting and his stunning base-running skills, Brock sparked the Cardinals into contention. Thanks in no small part to him, the Cardinals took advantage of the Phillies’ collapse to win the pennant and the World Series. Brock would go on to lead St. Louis to two more pennants and another world championship and was one of the icons of the team. Ask any Cubs fan and they’ll agree: If Brock had stayed in Chicago, the “Curse” would have ended a lot sooner.
25 Chicago White Sox: The Black Sox
The White Sox have a lot of regrets over the years. Many fans still grouse on how the team had Sammy Sosa in the early 1990s and then traded him away. Sosa and Frank Thomas could have made a fantastic power hitting pair to spark the White Sox up. But when you talk of their biggest mistakes, nothing can top the Black Sox. In the 1910s, Chicago was a strong team, winning the World Series in 1917 and in good contention. They were upset by the Reds in the 1919 World Series but still quite strong and in the mix for the pennant the very next year. But at the height of the race, the truth came out: Eight players had conspired with gamblers to throw the ’19 Series to the Reds for payoffs.
It was shocking to everyone, especially as the group included “Shoeless” Joe Jackson, one of the best players of his time.
Even though he knew it would cost them the pennant, owner Walter Comiskey had no choice but to suspend all the players. Each player would be banned from baseball for life and the loss of all eight crippled the team. They would win a pennant in 1959 but wouldn’t make another trip until 2005 when they won the World Series at last. If not for that conspiracy, the White Sox might have been a stronger team for quite a while.
24 Cincinnati Reds: Dismantling the Big Red Machine
In the early 1970s, the Cincinnati Reds were one of the strongest teams in baseball. From 1970 to 1976, the Reds won five NL West divisional titles, two pennants and back-to-back World Series. They had a fantastic roster with Pete Rose, Johnny Bench, Joe Morgan and Tony Perez, a powerhouse soon named “the Big Red Machine.” With a total of 953 wins during that period, the Reds were easily the best team in the National League and soon laying claim to the best in all of baseball. It was amazing to see them rise up…and equally stunning to see their fall.
After the World Series win, the Reds could only manage second place finishes the next two years but still remained in serious contention. But owner Dick Wagner wanted instant results and thus fired Sparky Anderson, the manager who built the Machine. He then instigated other terrible moves such as refusing to sign Rose to a big contract. Rose thus went to Philadelphia and soon led the Phillies to the World championship. The Reds managed a divisional title in 1979 but not much else. They did have the best record in 1981 but were kept out of the playoffs due to the strike that year and sunk further. It would take a decade for them to get back to the World Series as Wagner transformed the Machine into a battered pushcart.
23 Cleveland Indians: Trading Rocky Colavito
This is no shock at all. To any Cleveland fan, the decades of agony and heartbreak for the Indians can be traced back to this horrible move. The Indians were once a serious threat in the American League, often in the pennant mix, World champions in 1948 and a fantastic season in 1954. As 1960 began, the team was trying to build themselves back up and had a terrific star in Rocky Colavito. The man was the AL home run champion in 1959 and a terrific player as fans would wait hours for him to sign autographs and he was quite involved in the city’s various charities. But general manager Frank Lane had already traded a lot of talent for what he thought could be winners and thought Colavito was getting too old.
Thus, Rocky was sent to Detroit for Harvey Kuenn and Indians fans nearly rioted. Colavito was very unhappy as he loved the city and didn’t want to leave. He had a good career as a nine-time All-Star while Kuenn would slump badly. Most fans see this trade as a curse upon the team that caused their decades of heartbreak and kickstarted a slew of bad moves that have haunted Cleveland ever since.
22 Colorado Rockies: Drafting Greg Reynolds
In their defense, the Rockies haven’t made as many absolutely bone-headed decisions as other teams. They’ve had mistakes but not quite the horrific kind. However, a major one had to be in 2006 as they had Troy Tulowitzki but wanted to spark things up.
The 2006 draft gave them a chance at Clayton Kershaw, Tim Lincecum or Max Scherzer, all of whom would go on to become Cy Young winners. Instead, Colorado went with Greg Reynolds.
Reynolds would win fewer games in his career (six) than the three aforementioned pitchers had number of Cy Young Awards won (7). Just to make it work, all three of those guys would be drafted by NL West rivals to show up the Rockies more.
It was a really bad move by Colorado who did make a wild card spot in 2009 but then suffered a horrific slump with some of the worst records in franchise history. By getting any of those first three pitchers, not only would Colorado have improved, they’d have taken a key talent away from their divisional opponents as shown by their bad play. For all their promise, Colorado have only made three post-season appearances in their history and moves like this show how the team just can’t grasp the opportunities given to them.
21 Detroit Tigers: Trading John Smoltz
He’s not exactly a household name and in 1987 this didn’t make much waves. But in retrospect, few moves by the Tigers are utterly disastrous as this. John Smoltz grew up in Detroit and always cited playing for the Tigers as a dream come true. He was drafted by them in 1985 but got stuck in the minors and never played an actual game for them. He was traded to Atlanta in 1988 who saw his potential. Soon, Smoltz became part of the fantastic trio with Greg Maddux and Tom Glavine who sparked Atlanta into a powerhouse in the 1990s. Smoltz was part of the team that would win the World Series in 1995 to showcase his great skills.
Smoltz played a total of 22 seasons in the majors with four more World Series appearances, finishing his career with the Cardinals. He boasts a postseason record of 15-4, and 8 time All-Star and NL postseason MVP. He was elected to the Hall of Fame in 2015 in his very first year of eligibility. In other words, the Tigers gave away a guy who could have been the perfect “hometown hero” player to boost them up and thus it ranks among their worst moves ever.
20 Houston Astros: Letting Randy Johnson Go
It’s one thing to trade away a fantastic talent. It’s another to just let him literally walk out the door. After years of rough play, the Astros tasted the postseason in 1997. In 1998, they made a trade for Randy Johnson, already a multiple All-Star with Seattle and was rising up as one of the best pitchers around. Johnson provided a significant boost with a 10–1 record, a 1.28 ERA, and 116 strikeouts in 84⅓ innings. He added to it in the playoffs, posting a 1.93 ERA in 14 innings and just three earned runs. However, the rest of the team couldn’t match the effort and thus the Astros were eliminated. But given his fantastic record, one would think Houston would naturally want to extend Johnson’s contract. Instead, they decided not to renew it.
Johnson thus went to Arizona which was only in its second year of existence. Thanks to Johnson, the Diamondbacks were soon rising up as a great team and in 2001, reached the World Series. Johnson pulled off a stunning performance to win the Series for the Diamondbacks. Johnson himself was named MVP of the Series and the next year earned the pitching Triple Crown. Johnson was easily elected to the Hall of Fame (the first Diamondback uniform on a plaque) and it would take Houston until 2017 to get their World championship but could have gotten it earlier if they hadn’t let Johnson walk.
19 Kansas City Royals: Not Jumping to the National League
The Royals had seen a lot of ups and downs over their existence. They pulled off a stunning upset winning the World Series in 1985 but couldn’t keep that momentum going. They had bad turnover in the front office and some budget battles that kept them from getting some future stars. In 1997, MLB was planning a realignment due to the creation of the Diamondbacks and Devil Rays. Thus, the Royals were given an opportunity to move from the American League to the NL Central where they would be sharing a division with their in-state rivals the St. Louis Cardinals. However, the board decided against the move and thus Milwaukee made the switch instead.
There were various reasons this was bad. As part of the NL Central, the Royals would have been playing the Cardinals and the Cubs, two notable teams and that would have boosted attendance up.
Also, no designated hitter in the NL would have meant opening up the payroll without the need for an extra player. There also would have been less worries over handling the strong AL of the time as the Yankees were about to resurrect into a powerhouse. The Royals may have avoided their horrible period of the 2000s and may have won a World Series before 2015 with a simple move.
18 Los Angeles Angels of Anaheim: Signing Albert Pujols
Many may claim the worst mistake by the Angels is the fact they can’t decide on a regular name for their home city. They’ve been California, Anaheim, L.A., back to Anaheim and now a mix of the two. It’s an identity crisis that makes it harder to get behind them. But signing on Albert Pujols has to rank among the dumbest moves that is crippling the team. For some reason, MLB teams continue to make the mistake of handing out massive 10-year deals for guys in their 30s and it never works out. To be fair, Pujols was a great player in his prime, a two time World Champion with the Cardinals and a fantastic hitter. But by 2012, it was obvious he was on the downside of his career. Yet somehow, the Angels thought he was worth $254 million.
This is the team that has Mike Trout, a man who, by rights, should have led them to the World Series by now. Instead, they are saddled with a guy whose contract dictates he stays with them until 2021 and has yet to produce any serious impact to the game. Worse, his contract means the Angels don’t have the cash to reach out to more promising young players and has hampered them more. In their short-term desire for Pujols, the Angels ruined much of their push for the future.
17 Los Angeles Dodgers: The 60s Collapse
When the Dodgers moved to Los Angeles in 1958, it was a stunning moment for baseball. The team had been known as a mainstay of Brooklyn and fans couldn’t believe they were jumping ship like this. Their first year was rough but they won the World Series in 1959 and seemed like they'd be a powerhouse for the long haul. The Dodgers would dominate in the early 1960s, winning World championships in 1963 and 65 and boasting a great selection of players. Tops among them was Sandy Koufax, one of the best pitchers of his time and handling things well. However, the Dodgers did face challenges such as their ancient rivals, the Giants, starting to push a bit more.
Like too many “old-time” owners, Walter O’Malley didn’t grasp how things were changing and didn't make the right moves for the future. He traded some good players and failed to sign others while the move to divisional play never worked out for him. All told, the Dodgers were soon slumping and spent the 1970s mired near the bottom of the American League. It would take new ownership and hiring Tommy Lasorda to get the Dodgers back on top as a combination of terrible moves sunk them badly in that decade.
16 Miami Marlins: The 1998 Fire Sale
The book “The Best Team Money Can Buy” expertly goes into how Florida Marlins owner Wayne Huizenga opened up his check book massively to get his hands on the best players he could find. It was an overt grab of talent for cash but it paid off. In 1997, just their fifth year of existence, the Marlins went on a fabulous run, finishing the season 92-70 and made the playoffs as a Wild Card. Against all odds, they won the National League and then defeated the Indians in a thrilling World Series. The team was hot, was building a huge fanbase in Miami and easily could have kept themselves in contention for years to come.
Instead, Huizenga, claiming he had lost $34 million in that winning season and their payroll was cut down majorly. Thus, Huizenga went about with one of the biggest “fire sales” in sports history.
Over the course of the offseason, Huizenga sold or traded just about every single one of the players who had turned the Marlins into champions, leaving them a shell of themselves.
The result was an epic collapse as the Marlins went from World Champions to sixth place in one season. They did rebound to win another championship in 2003 only for another fire sale to ruin it. Rather than recognize the potential in a great team, Huizenga destroyed them at the height of their success.
15 Milwaukee Brewers: Trading Gary Sheffield
In their defense, the Brewers didn’t have much of a choice and at the time it looked like a good idea. In retrospect, it was a disaster. Sheffield was 23 but rising up with his hitting and fielding. However, an injury hurt his momentum and soon, he grew unhappy in Milwaukee. He was tearing into owner Bud Selig and admitted to blowing plays as a protest for his poor pay. Finally having enough of his attitude, the Brewers sent him to the Padres for three other players. None of those players would make any sort of impact and the Brewers spent the ‘90s hanging near the cellar of baseball.
Meanwhile, Sheffield would have an okay time in San Diego with his attitude improving and he even won the NL batting title. Sheffield was then traded to the upstart Marlins and was a key player to lead them to the World championship in 1997. A nine-time All-Star, Sheffield retired in 2009 with over 500 home runs and was truly one of the great hitters of his time. Milwaukee might have felt right then in letting him go but it turned out to be a bad move down the line.
14 Minnesota Twins: Cutting David Ortiz
The Twins have had some notable years in their existence. They won World Series in 1987 and 1991 and often boasted some great teams. In the 2000s, the team was trying to rise up more and making some good moves to get ahead. Among the stacked roster was David Ortiz, rising up as a power hitter and impressing by carrying on through the 2002 season following the tragic death of his mother. However, Minnesota thought Ortiz was being hampered by injuries and costing them too much on the payroll. They thus decided to just cut Ortiz rather than try to negotiate for a multi-million dollar contract.
Ortiz was worried as he had just opened up a restaurant but luckily, his old friend Pedro Martinez talked the Red Sox into signing him on.
Before long, Ortiz’s power hitting was pushing Boston back into serious contention. Ortiz was a key figure in Boston’s return to the top, winning three World Series and named the 2013 Series MVP. A ten time All-Star and 7-time Silver Slugger award, Ortiz made the lives of pitchers miserable with his timely home runs. Retiring in 2016, “Big Papi” is a lock for the Hall of Fame and the Twins (who spent the last decade with horrible years) have to regret letting him go.
13 New York Mets: Passing on Reggie Jackson
The Mets have made a lot of terrible moves over the years. The team famously were a total joke for their first few years with bungling moves. They also instigated a near fan revolt by trading star Tom Seaver in 1977 which majorly hurt the team. But amid the joy of 1969, when the Mets won the World Series, is how they made a huge mistake that would hurt them down the road. Three years earlier, the Mets had a high rank in the draft thanks to their terrible run. They chose Steven Chilcott, an okay college player but would end up never playing a game for the Mets. They thus passed on a young slugger by the name or Reggie Jackson.
Jackson would end up in Kansas City and then joining the A’s when they moved to Oakland. There, his fantastic slugging was a key reason the A’s dominated baseball with three straight World championships. Jackson later went to New York where he revived the Yankees with two more championships and a two time World Series MVP and AL MVP. Thus, keeping Jackson could have turned the “Miracle Mets” into a dynasty in their own time and boost their power for years to come.
12 New York Yankees: Not Seeing the 1966 Collapse Coming
In 1964, the Yankees lost the World Series to the Cardinals but weren’t too upset. They were the Yankees, the powerhouse who had been in 14 of the last 20 World Series with 10 of those being victories. They had mega-star hitters and pitchers and most assumed they would continue to dominate. Instead, within two years, the Yankees were dead last in the American League. The fact is that the franchise had been set for a fall for years but refused to see it. They were victims of their own success, caring only for World titles and not making moves like trading aging stars for younger talent. Thus you had an older team who just couldn’t handle the changes in the baseball landscape.
Also, the Yankees let their farm system fall apart and neglected the need to develop younger players. Worst was the Yankees' reluctance to sign on black ballplayers even well after baseball had been integrated.
The short-sighted idea of only caring for the titles cost the Yankees as they spent a decade fallen from grace. It would take George Steinbrenner and his millions to revive them but there’s a good reason why Yankees fans refer to 1965 to 1976 as “The Dark Ages” of the dynasty.
11 Oakland Athletics: Committing to Moneyball
Many A’s fans will contend a huge mistake was how owner Charles Finley allowed the dynasty of the 1970s (which won three straight World Series) to fall apart by trading or selling away the major talent. However, perhaps more damaging has been the Athletics' stubborn commitment to the Moneyball system. The movie made it seem like it was sheer genius; picking players not by their fame but by how good they really were, spending less money for more talent.
To hear Billy Beane tell it, you’d think this system is one of the most revolutionizing in history and has allowed Oakland to dominate baseball. Of course, there is one tiny little flaw in this theory - it’s yet to produce a single championship team.
Sure, Beane did great, pulling in guys like Zito, Hudson, and Mulder, plus MVPs in Jason Giambi and Miguel Tejada. Except all five were gone fairly quickly and in recent years, the A’s are slumping. They won two divisional titles but lost in the first round of playoffs and the last three seasons have been horrific. The brutal fact is, some guys are worth paying more, but Beane is dedicated to this style as somehow “the wave of the future.” Until they snap out of this thinking, the A’s are going to continue to suffer for some time to come.
10 Philadelphia Phillies: The 64 Flop
Nothing shuts up an arrogant Phillies fan like mentioning 1964. From Opening Day, the Phillies dominated the National League. They had a fantastic roster of pitchers with a great fielding group as well and manager Gene Mauch brilliant keeping them on track. The Phillies were amazingly dominant to the point that by mid-season, other teams in the NL had decided the race was lost and it was more important to look to next year. By September, the Phillies had a six and a half game lead with just 12 games left to play. They were literally printing up World Series tickets and programs and didn’t get too upset when they lost a game. And then another. And another. And…
At the worst possible moment, the Phillies lost 10 straight games. The team that seemed close to perfection suddenly came apart at once. Fielders made easy errors, their bats cooled and Mauch was heavily criticized for overworking his pitchers on just a day of rest. The Reds and the Cardinals stepped it up and in the end, the Cardinals ended up with the pennant and the World Series. The Phillies took a nose-dive instantly and the next decade had them mired at the bottom. It took until 1980 for them to win the World Series at last and that “Phillie Phlop” is still a terrible moment for the team.
9 Pittsburgh Pirates: Letting Barry Bonds Go
The Pirates have had some highs over the years like the fantastic 1960 World Series victory and Roberto Clemente making them a championship powerhouse in the early 1970s. But they also have had lows such as 20 straight losing seasons, a major league record. A great reason for the latter would have to be that in the early ‘90s, the Pirates were actually showing promise. They won three straight NL East titles and made it to the NLCS each year. A major reason was one Barry Bonds who was already showing his potential as one of the best sluggers out there. But Bonds wasn’t happy after the team traded his friend Bobby Bonilla and felt they should be paying Bonds, a two-time MVP, a lot more.
Letting Bonds go was one thing. But this was a man who could have garnered a huge price in a trade or even being sold off, for a major player who could've helped keep the Pirates in contention. Instead, they just let Bonds go without even getting anything in return. Bonds headed to the Giants where he instantly made them contenders, set the record for most home runs and (despite controversy over his alleged PED use) is regarded well for his hitting power. The Pirates, meanwhile, have spent the decades since mired near the bottom and can blame letting Bonds go for that.
8 San Diego Padres: Trading Ozzie Smith
Nothing causes Padres fans to grind their teeth together like this. In 1980, the club was trying to rise up and be a major player but were mired by various issues. Key among them was the stupid decision to let Dave Winfield go to the Yankees. But the Padres managed to outdo that idiocy the very next year by trading Ozzie Smith to the Cardinals. Smith had been showing his skills as a shortstop with great dives and throws while also being a good hitter. But the Padres just felt Smith was causing trouble demanding money and there was the famous moment of him taking out a newspaper ad offering his services for other available jobs in San Diego.
Thus, the Padres figured unloading Smith saved them some hassle. In no time at all, they were kicking themselves badly.
The very next year, Smith helped the Cardinals win the World Series.
Over the next 13 seasons, the “Wizard of Odds” became a St. Louis icon with his sharp play, great interviews and astounding backflips. A 15-time All-Star and MVP, Smith was easily elected to the Hall of Fame as one of the best shortstops of his time. All that could have been San Diego’s if not for some ego.
7 San Francisco Giants: Trading Gaylord Perry
Some will argue Gaylord Perry’s place in the Hall of Fame. While a skilled pitcher, Perry was also one of the most infamous spitball users in baseball and made no secret of it. However, the brash Perry did have a tremendous run as a pitcher and was showing it with the Giants in the 1960s as the team was struggling to get back on track after a few winning years. Perry was rising up and showing some serious promise but the Giants felt he was hampered by nagging injuries and were wary of signing on another star for their payroll. So in 1972, they traded Perry to the Indians.
Over the course of his career, Perry never earned a World Series win. However, he did end up with a no-hitter, a five-time All-Star and a two-time Cy Young winner. He retired with 314 wins, a 3.11 ERA and 3,534 strikeouts. Despite that “cheating” rep, he still earned a Hall of Fame spot and stuck it to the Giants, who spent the 1970s in a terrible slump. Perhaps keeping the ace pitcher Perry could have helped the Giants win the World Series a few decades earlier. At the very least, it would have kept them in contention for a lot longer.
6 Seattle Mariners: Letting A Future All-Star Team Go
In 1995, the Mariners were, like many teams, trying to bounce back after the players' strike cut the previous season short. They had a good team with Ken Griffey Jr, Randy Johnson and others and pushed themselves with the “Refuse to Lose” mantra. They did pay off on that, making it to the ALCS before losing to the Indians. They stayed in contention but in 1998, made several bad moves. First, they traded Johnson to the Astros where he’d spend a year before embarking on his Hall of Fame career that would earn him a World title. They then traded Griffey to the Reds and watched as he too would go on to have a fantastic career as one of the best hitters ever.
Then there refusing to see the potential in Alex Rodriguez, a rising rookie sensation. Rather than lock him down with a long contract, the Mariners let Rodriguez go to free agency and thus missed out on the fantastic star he would become. It took its toll to slump Seattle down and took years before they could rebuild. Seattle had three stars that any team would have paid huge bucks for and let them all go, a key reason this team has had a lot of rough years ever since.
5 St. Louis Cardinals: Trading Hernandez
In the annals of the worst trades in baseball history, this is one of the top picks. Keith Hernandez had been a terrific star for the St. Louis Cardinals, a top first baseman who was the 1982 National League MVP. Hernandez was a key factor in the Cardinals team that won the 1982 World Series and looked ready to continue with the team. But Hernandez was clashing with management who took a dim view of his substance abuse issues and were not keen on his future with the club. So in June of 1983, Cardinals fans were outraged when it was announced that the team had traded Hernandez to the Mets. The Cardinals became the first World championship team of the post-division era to fail to make the playoffs the next year, ending up in 4th place.
The Mets had no problems with Hernandez’s issues as he soon sparked the team up. In 1986, the Mets went on a fantastic year to win the World Series and Hernandez was a major part of that. He kept with them until 1989 and retired in 1990 amid talk of major substance abuse problems. But Hernandez has cleaned himself up and now a well-regarded broadcaster. Meanwhile, it would take the Cardinals over a decade to win the World Series again as trading Hernandez rocked the team hard.
4 Tampa Bay Rays: Letting Joe Maddon Go
The former Devil Rays are well known as having one of the worst track records for free agency signings out there. They have wasted millions on guys with little return and the results have not been good. But in the late 2000s and even the early 2010s, the Rays were rebounding thanks in no small part to the work of manager Joe Maddon. The skipper was great getting everyone on the same page, utilizing their talents and overcoming the lack of real star power to make them winners. They reached the World Series in 2008 and the Rays ended up in winning the AL East in 2010 and earned Wild Card berths in 2011 and 2013. It seemed they’d be rising up more but then Maddon had a falling out with management leading to him going to the Cubs.
Since then, the Rays have sunk badly. They haven’t had a winning season since and their best campaign has been a third place finish in 2017.
Meanwhile, just two years after reaching Chicago, Maddon would finally allow the Cubs to break “The Curse” and win the World Series in 2016 which makes him nothing short of a miracle worker. Thus, letting Maddon go was a serious blow that has caused the Rays to falter majorly.
3 Texas Rangers: Trading A-Rod
From the start, Alex Rodriguez had future star written all over him. He was exploding with talent, charisma and serious promise and should have been the guy to lead the Mariners to greatness. Instead, Seattle just let him go to free agency, allowing the Rangers to snatch him up. Rodriguez has said he regrets the move, feeling Texas never appreciated his work or his desire to help them out. He did his best, was named MVP and seemed ready to rise up but felt he deserved more money than Texas was willing to pay. Feeling it'd be better to free the payroll up, the Rangers traded Rodriguez to the Yankees after a plan to send him to Boston fell through.
As everyone knows, Rodriguez became one of the biggest stars of the current Yankee era. He helped provide a spark to the team with his great play and fantastic presence which was ideal for the hotbed New York media. He helped the Yankees win the championship in 2009 and while hampered by accusations of PED use, he still had many great moments in a Yankees uniform. Finally retiring in 2016, it’s likely A-Rod gets into the Hall of Fame despite controversy and his relationship with Jennifer Lopez keeps him in the limelight. Texas just gave that all away for one of the dumbest moves ever.
2 Toronto Blue Jays: Trading Roy Halladay
Oh, Toronto. Nothing hurts the fanbase more than this horrific move. Over the course of a decade, Roy Halladay was easily the star pitcher of the team, a 7-time All-Star, Cy Young winner and two 20-win seasons. He was a great star for the team and fans loved seeing him play. But Halladay felt his career winding down and concerned he couldn’t get that elusive World Championship with the Blue Jays. The Jays never even managed to make the postseason the entire time Halladay was on their roster, despite him arguably being the most reliable pitcher in the game.
Toronto felt his best days were behind him so in 2009 traded him to the Phillies for Kyle Drabek, Travis d'Arnaud and Michael Taylor.
Taylor never started a single game for Toronto; Drabek compiled an 8-15 record before he was waived in 2015; and d’Arnaud was actually showing promise before he was traded to the Yankees. Meanwhile, Halladay would continue for a few great years in Philadelphia where he earned another Cy Young award. Maybe keeping the “old man” over the younger guys could have helped Toronto build a better team rather than continue their terrible ways. It took several more years for the Jays to finally recover.
1 Washington Nationals: The Fire Sale
This is going back to before the team we know today as it still ranks as a horrific move. Ask any fan of the Montreal Expos and they will agree on one thing: If the players strike had never happened, the Expos would have been 1994 World Champions. The team was truly on the rise, a fantastic mix of players and it was all clicking wonderfully. Attendance was huge and thus Montreal fans were more crushed than anyone when the season was called off by the strike as championship glory was in their grasp. Thus, they were hopeful for 1995 to get back what should have been theirs. Sadly, in the interim, owner Claude Brochu over-reacted to the strike by thinking what the team needed was a “fresh start”, which was really code for "we don't want to pay these players".
Thus by Opening Day 1995, Brochu had gotten rid of many of the players who made the Expos contenders. Larry Walker, Marquis Grissom, Ken Hill, and John Wetteland were all sold or traded, a move that crippled the team. The Expos went from greatness to fifth place and never came close to being the contenders they were in '94. It caused the huge slump that would eventually lead to them being moved to Washington and becoming the Nationals. Sure, the strike was beyond their control but the fire sale is what truly crippled Montreal in so many ways.