Baseball is a thankless sport if you're a general manager.
Between free agents, trades and drafts, baseball GMs have a profound impact on the future of their respective franchises. They can find the diamond in the rough who becomes a cornerstone player during a World Series run, or they can grossly overpay for a veteran who's over the hill and leave their club financially strapped.
No GM or owner is perfect, but the ones responsible for the moves on this list may need more than a sleeping pill to be able to sleep at night.
Here is every MLB team's biggest regret ever.
Dmitriy Ioselevich is a Featured Columnist for Bleacher Report. Follow him on Twitter for all your MLB news and updates.
The Diamondbacks haven’t been around for too long, so they haven’t had a chance to make many mistakes, but the signing of Russ Ortiz in 2005 is pretty inexcusable.
It’s bad enough that the Diamondbacks broke up the Randy Johnson/Curt Schilling tandem, but then to add Ortiz to a rotation anchored by Brandon Webb? That’s like trading in a Mercedes for a Kia.
Ortiz was 15-9 with a 4.13 ERA in 34 starts for the Atlanta Braves in 2004, which apparently is the going rate for a four-year, $33 million deal.
However, the righty struggled in his first season in Arizona with a 5-11 record and 6.89 ERA. He was even worse in 2006, when he failed to win a single decision and was demoted to the bullpen, and he was eventually released midway through the season.
It’s not often you see players released with more than two years and $22 million left on their deals. But that’s just a testament to how bad Ortiz was.
The Braves were the Yankees of the National League during the 1990s, winning 11 division titles in a row from 1995-2005 and 14 in 15 years (with the lone exception being the strike-shortened 1994 season).
However, despite all that success, the Braves walked away with just one World Series title in that span (1995). They appeared in two additional World Series in 1996 and 1999 but lost both times to the Yankees.
Any Pirates fan would happily trade places with a Braves fan; however, it’s a small miracle that the Braves didn’t win more pennants than they did, especially considering they had three future Hall of Famers in their rotation (Tom Glavine, Greg Maddux, John Smoltz).
It doesn’t really count as a dynasty if you don’t win the biggest games.
Albert Belle was one of the best sluggers in baseball throughout the 1990s, earning four consecutive Silver Slugger awards as a member of the Cleveland Indians and five total in his career.
In 1996, the left fielder smashed 48 HR with a league-leading 148 RBI and a gaudy 1.033 OPS, good for third in MVP voting.
The Chicago White Sox were understandably impressed and handed Belle a five-year, $55 million contract that included an unusual clause that guaranteed Belle would remain one of the three highest-paid players in baseball.
Belle lasted two seasons in Chicago before the White Sox decided he wasn’t worth the money anymore, and he became a free agent, signing a five-year, $65 million deal with the Orioles.
Belle never made an All-Star team as an Oriole despite two relatively productive seasons and was out of baseball by 2000 due to a degenerative hip condition. The Orioles were still responsible for honoring his contract and kept Belle on the 40-man roster for three more years.
They haven’t been out of the AL East cellar since.
This is still one of the worst decisions in the history of professional sports, and one that the Red Sox continue to regret despite two world championships in the last decade.
Boston owner Harry Frazee needed cash to finance his play No, No, Nanette and wasn’t a big fan of Ruth to begin with, so he traded his best player to his archrivals in New York for $100,000.
Ruth would lead the Yankees to three World Series titles in 15 incredible seasons, while the Red Sox wouldn’t win another title for 86 years. The Curse of the Bambino may be broken, but it will never be forgotten.
It’s not quite as well known as the Babe Ruth story, but its perceived impact on baseball may be just as monumental.
In 1945 Billy Goat Tavern owner Billy Sianis was asked to leave a World Series game at Wrigley Field because his pet goat was disturbing some of the fans. In response, Sianis lost his cool and declared, “Them Cubs, they ain’t gonna win no more.”
True to this word, the Cubs have not returned to the World Series since 1945 and haven’t won a world championship since 1908. The Cubs now have the longest active championship drought in professional sports, with no end in sight.
What actually happened that day in 1945 is still up for debate, but we do know that a goat was involved and a curse was declared. The rest is history.
The White Sox have had plenty of bad trades and signings, but the one event that management will never be able to shake off the stigma from is the Black Sox Scandal.
In 1919, eight members of the Chicago White Sox conspired to throw the World Series in return for a large financial payoff through underground betting.
You can blame club owner Charles Comiskey and his refusal to pay his players fairly (Eddie Cicotte in particular), but intentionally losing the biggest games of the year is something that’s looked down upon among even the seediest members of society.
These eight players (including the great “Shoeless” Joe Jackson) were banned for life and their accomplishments wiped from the annals of baseball history. It’s hard to imagine any way the always unpredictable Ozzie Guillen could ever top this one.
It’s not really fair to blame the entire Cincinnati Reds organization for the mistakes of one man, but Rose is such a major baseball figure that it’s hard not to do it.
The all-time major league leader in hits was a Reds legend during the 1970s, when he won three World Series titles and was the leader of the Big Red Machine. However, all the accolades in the world still won’t get Pete Rose into the Hall of Fame.
In 1989 Sports Illustrated ran a story alleging that Rose bet on baseball while a player and a manger for the Reds. Rose denied the allegations, but nonetheless, two years later the Hall of Fame voted to ban him from induction.
There have been movements to get Rose reinstated, especially after he finally admitted to betting on baseball in 2004. However, he remains an outcast from the game and a dark shadow on Cincinnati sports.
In what is affectionately known as the Curse of Rocky Colavito, the Indians traded their star slugger to the Detroit Tigers for Harvey Kuenn just before Opening Day in 1960.
On the surface, it seemed like a fair deal. Colavito was the AL co-home run champion, and Kuenn was the AL batting champion and hits leader. Colavito was three years younger, but Kuenn could play in both the infield and outfield. What could possibly go wrong?
Well, apparently a lot when GM Frank “Trader” Lane is involved. Kuenn only lasted one season in Cleveland, albeit a productive one, before being traded to the Giants for a couple of bags of peanuts.
Colavito, on the other hand, played four seasons in Detroit and hit another 139 home runs, earning two All-Star selections.
It would take another 35 years for the Indians to make the playoffs again, even though they reacquired Colavito in 1965. Cleveland hasn’t won a World Series since 1948.
The year 2000 will be best remembered for massive free-agent spending. Alex Rodriguez, Manny Ramirez and Mike Mussina all signed mega-deals worth millions of dollars, and the Rockies somehow ended up with Mike Hampton.
Hampton won 22 games in 1999, nearly taking home the NL Cy Young in the process, and was widely considered one of the top free-agent arms on the market. Colorado gave him an eight-year, $121 million deal that, at the time, was the richest in sports history.
Hampton returned the favor by going 14-13 with a 5.41 ERA in his first season and 7-15 with a 6.15 ERA in his second season. The right-hander would only make 62 starts in a Colorado uniform before being traded first to the Marlins and then the Braves.
Injuries contributed to Hampton’s decline, but there’s a reason pitchers don’t get long-term deals anymore—they’re just so unpredictable.
Any time you trade away a future Hall of Famer, there’s always going to be some level of regret. But this particularly stings because the Tigers got almost nothing in return.
Doyle Alexander was a relatively accomplished pitcher at the time of the trade, with 165 career wins for seven different teams. In the year before he was traded from the Braves, he even finished sixth in Cy Young voting.
However, Alexander would only make 67 starts in a Tigers uniform, and despite a late All-Star selection, his career hardly compares to Smoltz’s.
Smoltz spent 20 years with the Atlanta Braves and picked up 210 wins, 3,110 strikeouts, 154 saves and eight All-Star selections. He won the Cy Young Award in 1996 and finished in the top 10 in voting an additional four times.
The Marlins might be one of the most secretly lucky teams in baseball. They’ve only made the playoffs twice in franchise history, and both times they won the World Series as a wild card.
However, owner Jeffrey Loria was never particularly interested in paying his best players, and so after each World Series title, the Marlins had to completely blow up their roster. (It should be noted that Loria has only owned the Marlins since 2002, five years after they won their first world championship.)
Beginning in 2004, Loria has forced team management to jettison club favorites like Mike Lowell, Josh Beckett, Dontrelle Willis, Miguel Cabrera and, most recently, Dan Uggla to avoid paying them.
Loria has been under pressure by some of baseball’s other owners to spend more on players, but the Marlins still remain near the bottom of the league in payroll.
Despite this, Loria somehow fleeced the city of Miami into agreeing to build the Marlins a new, publicly financed stadium for 2012.
There’s overpaid, there’s grossly overpaid and then there’s stealing. Carlos Lee managed to qualify for all three in his five seasons in Houston.
Lee was one of baseball’s best sluggers in 2006, when he hit 37 HR with 116 RBI and an .895 OPS between Milwaukee and Texas. The Astros wanted a big bat to replace Carlos Beltran and opted to sign Lee to a six-year, $100 million deal.
Lee seemed worth the price of admission at first, playing in all 162 games for the Astros in his first season and earning an All-Star selection and Silver Slugger award. However, injuries and general apathy contributed to his precipitous decline over the years.
This season, Lee has only 11 homers and a .749 OPS that would be a career low if it wasn’t for his stink-fest last season. He’s making $18.5 million this season and is due another $18.5 million next season, if his buffet-style diet doesn’t kill him first.
Perhaps the Astros would’ve been able to keep Hunter Pence and Michael Bourn long-term if they weren’t paying Lee to eat cheeseburgers between innings.
It’s been a long time since the Royals were any good, and the chief reason for that is a horrific streak of drafting.
Between 1992 and 2001, Kansas City never drafted below 17th in the first round and had three top-five selections. Of those 10 picks, four never even made it to the majors, and the ones who did were all pitchers with ERAs well over 5.00.
The MLB draft is generally considered a crapshoot, but even a team like the Mets gets lucky once in a decade. Among the players the Royals could have drafted are Chase Utley (2000), Barry Zito (1999), Brad Lidge (1998), Lance Berkman (1997) and Derrek Lee (1993).
They’ve been much better as of late with Zack Greinke (2002), Alex Gordon (2005) and Aaron Crow (2009), but the Royals are still in the middle of a 20-year-old rebuilding movement.
Mo Vaughn was one of the most feared sluggers in baseball during his time in Boston, accumulating 230 home runs in nine seasons and being named to three All-Star teams. He also won AL MVP in 1995 after leading the league with 126 RBI.
Vaughn was just 30 years old and coming off a 40-HR season when the Angels signed him to a six-year, $80 million contract in 1998. Sluggers tend to age pretty well, but unfortunately, in Vaughn’s case, his 30s were not particularly kind to him.
His numbers declined each of his first two seasons in Anaheim, and injuries forced him to miss all of the 2001 season. He was eventually traded to the Mets in 2002 for Kevin Appier, conveniently the same year that the Angels won the World Series.
Vaughn finished his Angels career with just 69 homers and a .276/.362/.503 line during his two injury-shortened seasons, a far cry from his Boston days and hardly worth an eight-figure salary.
The Dodgers would probably love to take back the $45 million they gave Manny Ramirez to take female fertility drugs, but Manny’s antics don’t even scratch the surface of what Frank McCourt has done to this franchise.
The former Boston real estate developer purchased the Dodgers in 2004, a purchase that was actually financed mostly by debt. Financial ruin became a hallmark of the McCourt ownership, as the Dodgers were forced to raise ticket and concession prices every year just to make ends meet.
If that wasn’t bad enough, McCourt's very public divorce with his wife Jamie became a major distraction for the club. Then on June 27, the Dodgers filed for Chapter 11 Bankruptcy protection, forcing McCourt to essentially surrender control of his franchise to MLB.
We’ve only begun to see the fallout from McCourt’s ineptitude. The situation in Los Angeles is only going to get worse before it gets better.
Bichette showed promising power potential early in his career in Milwaukee, with 38 home runs in over 400 games. However, the Brewers weren’t impressed enough to give him a starting job and in 1992 traded him away to the Rockies for Kevin Reimer.
Reimer only played one season for the Brewers before retiring at the age of 29; however, Bichette went on to have a long and fruitful career for the Rockies.
In seven seasons in Colorado, he blasted 201 of his 274 career HR and became one of the preeminent sluggers of the decade.
He carried the Rockies to the playoffs in 1995 after hitting 40 HR with 128 RBI, finishing second in MVP voting. He was also named to four All-Star teams.
Ortiz wasn’t even a full-time player in Minnesota, even though he began showing flashes of his prodigious power by his mid-20s. He had his best season for the Twins in 2002, when he hit 20 HR and finished with a career-high .839 OPS.
However, the Twins apparently weren’t impressed because they released the 26-year-old Ortiz. The Red Sox picked him up for just $1.25 million, and the rest is history.
In nine seasons in Boston, Ortiz has 313 home runs and a .956 OPS. He finished in the top five in MVP voting in each of his first five seasons for the Red Sox, forming one of the most fearsome hitting tandems in baseball history with teammate and best friend Manny Ramirez.
In the Twins’ defense, the Red Sox didn’t even think Ortiz would start initially. But for whatever reason, Big Papi found his groove and is now considered one of the best hitters in Red Sox history.
Bonilla was a bona fide star in Pittsburgh, where he teamed up with Barry Bonds and Andy Van Slyke to form a devastating Pirates team.
The Mets pried him away in 1991 after four consecutive All-Star selections by making who they thought was the best player in baseball the highest-paid player in baseball with a five-year, $25 million deal.
Bonilla never delivered in New York, as his power declined and injuries forced him to miss large chunks of the season. He did make two All-Star teams, but he was hardly the middle-of-the-order thumper the Mets thought they were getting.
The Mets traded him to the Orioles in 1995 and agreed to defer the remaining $5.9 million of his contract until 2011 at eight percent interest. In translation, that means the Mets owe Bonilla more than $29 million over the next 25 years, with the first payment going out last month.
The Mets would later reacquire Bonilla in 1999, during which time he played badly and fought with manager Bobby Valentine. This could only happen to the Mets.
The Yankees have had more than their share of bad trades (Mike Lowell), draft picks (Brien Taylor) and free-agent signings (Jose Contreras), but no single player could damage the Yankee legacy as much as the Red Sox did in 2004.
Up 3-0 with a 4-3 lead in the ninth inning of Game 4 of the ALCS, the Yankees suffered the greatest collapse in the history of professional sports. The immortal Mariano Rivera walked Kevin Millar, Dave Roberts stole the base heard around the world and the Red Sox came back to tie the game and eventually win it in the 12th inning.
The Yankees had another chance to shut the door in Game 5, but the Red Sox again came through late in the 14th inning for the 5-4 win. Neither Game 6 nor Game 7 was ever close, as the Red Sox became the first team in baseball history to come back from a 3-0 deficit in a playoff series.
The Red Sox would go on to win the World Series, breaking the Curse of the Bambino and bringing salvation to millions of tortured Red Sox fans. As for the Yankees? They’re still trying to figure out how they lost.
Billy Beane is known as someone who tends to do his homework when it comes to a transaction. However, the Moneyball Golden Boy must have misread a scouting report when he inked Loaiza to a three-year, $21.4 million deal.
Loaiza was a moderately successful pitcher who played in two consecutive All-Star games from 2003-2004. He was even 12-10 with a 3.77 ERA with the Nationals in 2005 the year before he joined the Athletics. However, he was also 33 years old with a career hit rate of 10.1 H/9.
Aging pitchers without overpowering stuff don’t tend to do well, and neither did Loaiza. The righty ended up making only 28 starts with Oakland, as injuries and ineffectiveness sent his career into a tailspin. Loaiza was waived after a little more than a season and was out of baseball just a year later.
The Phillies knew what they had in Schilling when they traded him to the Diamondbacks in 2000. He already had more than 100 career wins, over 1,500 strikeouts and three consecutive All-Star selections.
Schilling was a certifiable ace and workhorse who carried the Phillies to the World Series in 1993 in just his sixth professional season. How the Phillies didn’t get a single productive player in return for him is an epic failure.
Sent to Philadelphia were pitchers Omar Daal, Nelson Figueroa and Vicente Padilla and a young first baseman named Travis Lee.
Daal made just 44 forgettable starts for the Phillies, Figueroa lasted just 13 games, Padilla made 111 decent starts but was a headcase and Lee just never developed.
Schilling, meanwhile, went on to win the World Series with the Diamondbacks in 2001 and then again with the Red Sox in 2004 and 2007. Whoops.
In Bonds’ final three seasons in Pittsburgh, the Pirates went 95-67 (1990), 98-64 (1991) and 96-66 (1992) and made it as far as the NLCS each year. In the three years following Bonds’ departure, the Pirates were 75-87 (1993), 53-61 (1994) and 58-86 (1995).
Suffice it to say, the Pirates missed Barry Bonds. The now infamous slugger was quickly developing into one of the game’s best all-around players during his early days in Pittsburgh.
Bonds could hit for power, hit for average and steal some bases. He was even a terrific outfielder and was named the MVP in both 1990 and 1992.
The Pirates, however, didn’t make a strong effort to re-sign Bonds when he became a free agent in 1992 and lost him to the San Francisco Giants.
Bonds would eventually become the premier slugger of his time and perhaps all time, shattering the single-season and career home run records and taking home five additional MVP awards.
However, considering how Bonds’ career ended (without a title and with heaps of public scorn), perhaps the Pirates aren’t too broken up about this one.
There are two ways that a small-market team can compete in today’s modern baseball landscape: spending smart or drafting smart. Sometimes it has to be both. Unfortunately for the Padres, they whiffed badly when they drafted Matt Bush No. 1 overall in the 2004 MLB draft.
The home product and shortstop was a legitimate five-tool talent that San Diego executives dreamed would be roaming Petco Park for at least a decade. However, Bush never made it past A-ball and finished with a career line of .219/.294/.276 in five minor-league seasons.
What makes this one worse is that the Padres could have had their pick of Justin Verlander (No. 2), Jered Weaver (No. 12) or Stephen Drew (No. 15), but all were deemed difficult signs. Instead, the Padres ended up with Bush for $3 million.
They might as well have spent the money on hot dog stands.
The Giants haven’t always been shrewd about how they spend their dollars (see: Zito, Barry), but the scouting department generally did a good job of identifying which prospects projected to be major leaguers. Unfortunately, whichever scouts signed off on the Pierzynski deal should be fired.
The Giants got the veteran catcher they wanted in Pierzynski, who hit .272/.319/.410 in his one season in San Francisco. However, the price was astronomical.
The Twins happily accepted an offer of Boof Bonser, Francisco Liriano and Joe Nathan. All three made it to the major leagues, with Liriano briefly showing promise as a staff ace before undergoing Tommy John surgery and Nathan becoming one of the best closers in baseball.
The Giants seem to be doing all right without these three players, but there are few trades in baseball history as lopsided as this one.
The 1997 Mariners wanted another reliever to fuel their playoff run, and they settled on Heathcliff Slocumb, a productive middle reliever who saved 27 games during a season and a half in Seattle.
However, the price for Slocumb was two young players that would go on to have incredibly productive major league careers: Derek Lowe and Jason Varitek.
Lowe spent eight seasons in Boston, winning 70 games and saving another 85. He was an integral piece of the 2004 World Series team.
Varitek became the captain and leader for the Red Sox, earning three All-Star selections and winning two world championships in the process.
The lesson, as always, is never to overpay for a reliever.
The Cardinals didn’t think the 29-year-old Hernandez had much left when they traded him to the Mets in 1983, despite the fact that the first baseman had won six consecutive Gold Gloves and was just five years removed from an MVP performance.
As it turned out, the Cardinals were very wrong. Hernandez nearly won the MVP in his first full season in New York and was selected to three additional All-Star teams. He also won the Gold Glove five more times and was a key figure in the Mets’ 1986 championship run.
In return, the Cardinals got reliever Neil Allen and starter Rick Ownbey. Allen briefly served as the St. Louis closer before succumbing to a setup role, while Ownbey made just seven starts for the Cardinals before retiring at the age of 28.
The Cardinals have made several lopsided deals in the wrong direction, including trading Dan Haren for an injury-riddled Mark Mulder (2004) and trading ace Steve Carlton for someone named Rick Wise (1972).
Tropicana Field opened in 1998 after a long debate over where to put a new franchise. MLB settled on Tampa Bay, and the Devil Rays were born.
What MLB failed to take into account, however, is that there are no baseball fans in Tampa Bay. Even when the Rays became good, the franchise still had some of the lowest attendance figures in the league.
Another problem is that Tropicana Field was built in 1990 in an attempt to entice a major league franchise to relocate there, but by the time the Rays were born, the stadium was already in need of repair.
It may only be a matter of time before MLB gives up on the city of St. Petersburg and awards the Rays to someone else.
The Rangers had no way of knowing that the 20-year-old Sammy Sosa who debuted in Texas in 1989 would go on to become one of baseball’s greatest sluggers. After all, in his first 25 games, he had just one home run and 20 strikeouts.
The Rangers flipped Sosa to the White Sox for Harold Baines, who then traded Sosa again to the Cubs for George Bell. Both deals are in contention for being the worst trades ever.
It took Sosa until his fifth professional season, but by 1993 he was a legitimate power threat. Sosa is still the only player in major league history with three seasons of at least 60 home runs (including a career-high 66 in 1998) and is seventh on the all-time list.
The Blue Jays once thought they had a superstar in Vernon Wells.
The former No. 5 overall pick of the 1997 draft was a five-tool talent with plus power and plus-plus speed. In his breakthrough season for the Blue Jays in 2003, he hit 33 HR with 117 RBI and a .317/.359/.550 line. Wells had a nearly identical season in 2006.
The Blue Jays were impressed enough with his performance to reward their supposed franchise player with a seven-year, $126 million deal in 2006.
It took less than half a season for the Blue Jays to realize they had made a grave mistake, and GM Alex Anthopoulos pulled off the unthinkable by dealing Wells to the Angels last offseason for two role players.
Wells is now due $21 million for each of the next three seasons even though his power has declined, his speed has disappeared and his plate discipline has jumped off the roof. He’s not even a Gold Glove-caliber defender anymore.
It’s hard to quantify just how much the Nationals (Montreal Expos at the time) regret this deal. After all, Colon was terrific in his 17 starts for the Expos in 2002, going 10-4 with a 3.31 ERA and four complete games.
However, 17 decent starts is hardly worth what the Expos gave up in this deal. The Indians are still reaping the benefits from a package that included second baseman Brandon Phillips, pitcher Cliff Lee and outfielder Grady Sizemore.
Phillips has spent most of his career in Cincinnati, and Lee was traded to the Phillies in 2008 for Carlos Carrasco and Jason Donald, but the haul of three future perennial All-Stars for a two-month rental is still a pretty impressive one.
Where would the Nationals be today if they still had this trio? I’m guessing not last place.