Biggest Mistake in History for Every MLB Team

All 30 MLB franchises have had their Bill Buckner moment. Or worse.

Biggest Mistake in History for Every MLB Team

Boston Red Sox first baseman Bill Buckner leaving Shea Field after their Game 6 loss to the New York Mets in the 1986 World Series

Every human makes at least one regrettable mistake. Then there’s Bill Buckner, who committed the Exxon Valdez, Titanic iceberg and Mrs. O’Leary’s mad cow of baseball blunders. But he was never allowed to live it down.

Buckner was an All-Star-caliber player for many of his 22 seasons. But he’s not best known for his 2,715 career hits. Or even his batting title. Oh, no. Billy Buck will forever be the Boston Red Sox villain who allowed a slow ground ball to roll through his legs in Game 6 of the 1986 World Series, Charlie Brown style.

So egregious was the mistake made out to be, one thought that he had booted Game 7, too. The poor guy was harassed to the point that he moved to an Idaho ranch and died a bitter man. That just ain’t right.

Ranking Every MLB Team's Bill Buckner Moment

Babe Ruth with the Boston Red Sox in 1919

The truth is, every franchise has had their Bill Buckner moment. Or even worse.

These are the worst mistakes in MLB history for all 30 teams.

And we ranked them, from bad to unforgivable.

30. Washington Nationals: Jonathan Papelbon Disaster

Washington Nationals relief pitcher Jonathan Papelbon

Years: 1969-present (53 seasons, started as Montreal Expos)

World Series championships: 1 (2019)

Bottom Line: Jonathan Papelbon Disaster

In the heat of the 2015 playoff race, the first-place Nationals acquired closer Jonathan Papelbon to seal the deal. But it wasn’t long before Hurricane Pap attempted to strangle laggard teammate Bryce Harper amid charges that manager Matt Williams had lost control of the team.

After the Nats faded badly down the stretch, Papelbon was released late the next season. The price was a steep one. The organization ate the final $3.3 million of his contract, Williams was canned after the season, and the pitcher never threw a pitch in the majors again.

The unceremonious ending of Papelbon's time in the Show was a far cry from the beginning, when the hard-throwing closer looked bound for Cooperstown after saving 219 games for the Red Sox over seven seasons and winning a World Series in 2007.

29. Detroit Tigers: Jim Bunning Trade

Years: 1901-present (121 seasons)

World Series championships: 4 (1935, 1945, 1968, 1984)

Bottom Line: Jim Bunning Trade

The John Smoltz-for-Doyle Alexander trade is often mentioned here, but we’ll take a pass. We tend to forget that his new team was on the brink of two mostly dreadful decades, so Smoltz wasn’t likely to be a huge difference-maker.

We're going with the premature exit of another future Hall of Fame pitcher after the 1963 season. Only this one was proven already. That would be Jim Bunning, who single-handedly could have turned four 85-plus-win teams into contenders.

He won no fewer than 74 games with the Philadelphia Phillies in that span. Tiger general manager Jim Campbell got next to squat in the five-player theft.

28. Milwaukee Brewers: 1982 World Series Meltdown

Milwaukee Brewers third baseman Paul Molitor bobbles ball in 1982 World Series

Years: 1969-present (53 seasons, started as Seattle Pilots)

World Series championships: 0

Bottom Line: 1982 World Series Meltdown

St. Louis Cardinals runner Ozzie Smith scores in the 1982 World Series as the ball gets past Milwaukee Brewers catcher Ted Simmons

The Brewers played Game 7 of the 1982 World Series against the St. Louis Cardinals on the road at Busch Stadium.

Even with Milwaukee supersaver Rollie Fingers unavailable, the visitors took a 3-1 lead against the Cardinals into the sixth inning of the seventh game. Then, Brewers manager Harvey Kuenn stayed with overworked southpaw Bob McClure for one batter too long. Righty George Hendrick delivered an RBI single to cap a three-run rally, which proved to be the difference in a 6-3 outcome.

The Crew still haven’t won a Fall Classic in their long and meh history.

A close second: The $119.1 million that management donated to cheatin’, lyin' Ryan Braun over the 2013-20 seasons.

27. Toronto Blue Jays: 1987 Meltdown

Years: 1977-present (45 seasons)

World Series championships: 2 (1992, 1993)

Bottom Line: 1987 Meltdown

Toronto Blue Jays shortstop Tony Fernández

"We should have had three (World Series) rings with the team we had," outfielder Jesse Barfield said of the 1985-87 Blue Jays teams that averaged 94 victories per season. "Why it didn’t happen, I don’t know."

Here’s how: In Game No. 156 of the '87 season, with a chance to take a 4 1/2-game lead over the Detroit Tigers in the division race, Toronto manager Jimy Williams yanked starter Jim Clancy after only 79 pitches with a 1-0 lead that the bullpen frittered away.

Then Williams bypassed veteran closer Tom Henke in favor of rookie Jeff Musselman in another late fade against the Tigers on the next-to-last day of the season. The Blue Jays finished two games out of first.

26. Baltimore Orioles: Manny Machado Contract Screw-Up

Baltimore Orioles hitter Manny Machado follows through

Years: 1901-present (101 seasons, started as Milwaukee Brewers, then St. Louis Browns)

World Series championships: 3 (1966, 1970, 1983)

Bottom Line: Manny Machado Contract Screw-Up

Manny Machado smiles while rounding bases

In 2015, third baseman Manny Machado proved that his bum left knee was healthy again in a 35-home run, Gold Glove Award season. At that point, it was time for general manager Dan Duquette and his co-conspirators to lock up the 23-year-old well past his arbitration years.

But nooooo, the young stud was dealt to the Los Angeles Dodgers before he became a free agent three years later. The return was five suspects, none of whom ranked higher than No. 4 in the Dodgers farm system.

And the O’s have been in search of a bona fide star ever since.

Also considered: The 1991 Glenn Davis-for-Steve Finley-Pete Harnisch-Curt Schilling trade.

25. Arizona Diamondbacks: 2009 Draft

Baseball commissioner Bud Selig with Mike Trout

Years: 1998-present (24 seasons)

World Series championships: 1 (2001)

Bottom Line: 2009 Draft

The organization had a rare chance to grab the National League West by the mangoes in the 2009 draft, with five of the first 35 picks on the board.

General manager Josh Byrnes and company passed on a once-in-a-generation talent named Mike Trout not once but twice in favor of first baseman/third baseman Bobby Borchering and center fielder AJ Pollock in round one.

Paul Goldschmidt prevented an unmitigated disaster seven rounds later, but oh, what might have been.

24. Minnesota Twins: David Ortiz Release

Years: 1901-present (121 seasons, started as Washington Senators)

World Series championships: 2 (1987, 1991)

Bottom Line: David Ortiz Release

David Ortiz celebrating with Twins teammates

David Ortiz made his big league debut with the Twins in 1997 and hit 58 home runs in 455 games over six seasons with Minnesota.

In 2002, the soon-to-be Big Papi saw his home runs (20) and slugging percentage (.500) increase for the third consecutive season. The designated hitter was just shy of 27 years old with a reasonable $950,000 salary.

Twins general manager Terry Ryan didn’t want to pay the man and claimed they couldn’t trade him. So they released him one month later. What?! What were Ryan and the Minnesota brain trust thinking here? Were they thinking at all?

23. Texas Rangers: Nelson Cruz Tip-Toe Through the Tulips in 2011 World Series

Texas Rangers outfielder Nelson Cruz can't come up with triple off David Freese

Years: 1961-present (61 seasons, started as Washington Senators)

World Series championships: 0

Bottom Line: Nelson Cruz Tip-Toe Through the Tulips in the 2011 World Series

Texas Rangers hitter Nelson Cruz reacts to pop fly

The Rangers were one strike away from their first (and still only) World Series title in Game 6 of the 2011 World Series against the St. Louis Cardinals when David Freese hit a high fly ball to deep right field. Rather than go balls to the wall (only the World Series was on the line, right?), Nelson Cruz half-stepped it, more concerned about his health than the ball and his team.

He made a half-hearted leap barely on the warning track, only to have the ball sail a foot beyond his glove for a two-run triple that tied the score. The Cardinals went on to win the game, then the World Series one night later.

Instead of being a World Series hero — Cruz hit a solo homer two innings earlier — the guy became an all-time loser.

22. New York Mets: Nolan Ryan Trade

Years: 1962-present (60 seasons)

World Series championships: 2 (1969, 1986)

Bottom Line: Nolan Ryan Trade

California Angels pitcher Nolan Ryan fires pitch

Nolan Ryan had a 29-38 record and 3.58 earned-run average at the time of the 1971 transaction, but the 23-year-old had shown flashes in his four-year stay with the Mets. See the 1969 postseason.

It didn’t make sense to give up on an electric arm like this one, especially if the return was no more than broken-down shortstop Jim Fregosi, who was brought in to fill a chronic hole at third base.

Nobody knows if the Amazins would have been a perennial contender with future Hall of Famers Ryan and Tom Seaver at the top of the rotation, but it sure would have been fun to find out.

21. Tampa Bay Rays: Tropicana Ballpark Issue

Years: 1998-present (24 seasons)

World Series championships: 0

Bottom Line: Tropicana Ballpark Issue

Call us cray-cray (and thanks for the compliment), but we're among those who believe that major league baseball can make it in central Florida.

But we’ll never really know until the team plays in a cool new ballpark instead of Tropicana Field, the godforsaken dump that a few thousand pounds of dynamite wouldn’t make better.

20. Kansas City Royals: Failed Glory Years in the 1970s

Years: 1969-present (53 seasons)

World Series championships: 2 (1985, 2015)

Bottom Line: Failed Glory Years in the 1970s

Kansas City Royals manager Whitey Herzog

In 1974, Sleepy Joe Burke inherited a solid young nucleus from general manager Cedric Travis, then proceeded to go about his business like Archie Bunker in a depression.

As manager Whitey Herzog once hinted, "In spite of what the top echelon says, we’ve got to get off our rears."

Sure enough, a fatal flaw consistently bit the boys in blue in the butts come playoff time. There was ample reason to expect more than a 7-16 record in five postseason appearances.

19. Los Angeles Dodgers: Tom Seaver Snub

Tom Seaver throws against Philadelphia Phillies

Years: 1884-present (138 seasons, started as Brooklyn Athletics/Grays/Bridegrooms/Superbas/Robins/Dodgers)

World Series championships: 6 (1959, 1963, 1964, 1981, 1988, 2020)

Bottom Line: Tom Seaver Snub

New York Mets pitcher Tom Seaver in action

Dodger Blue began the 1970s with six second-place finishes in seven seasons. If Sandy Koufax hadn’t been mishandled to the point of early retirement or if Tom Seaver had been signed instead of insulted, might either future Hall of Fame pitcher have led the team to another World Series title or two?

Tom Terrific was the safer bet. In 1965, the Dodgers could have had the 20-year-old USC product for a $50,000 bonus, but they countered with a lowball offer. Seaver signed with the New York Mets eventually, and we know what happened next.

Don’t forget: The 1962 nosedive.

18. Cleveland Indians: Shoeless Joe Jackson Heist

Years: 1901-present (121 seasons, started as Cleveland Blues/Bronchos/Naps)

World Series championships: 2 (1920, 1948)

Bottom Line: Shoeless Joe Jackson Heist

If the Indians hadn’t parted with Shoeless Joe Jackson after six seasons, during which he put up a monstrous .375/.441/.542 stats line, the team would have been in position to win four World Series in a row. And the luckless outfielder might be in the Hall of Fame today.

Instead, the 27-year-old was dealt to the Chicago White Sox for $31,500 in cash and one serviceable player, got caught up in the 1919 World Series fix, and was banned from baseball for life.

This much we know. The futures of the primary parties involved couldn’t have turned out much worse.

In the mix: The 1960 Rocky Colavito trade and the 2006 World Series, Game 7, ninth inning.

17. California-Anaheim-Los Angeles Angels: Fatal Donnie Moore Pitch

Years: 1961-present (60 seasons)

World Series championships: 1 (2002)

Bottom Line: Fatal Donnie Moore Pitch

In Game 5 of the 1986 ALCS, the Angels were one out away from the World Series. The normally reliable Donnie Moore entered the game with a 5-4 lead against the Boston Red Sox and a runner on first base. Dave Henderson hit a fat splitter for a two-run homer, and the Red Sox went on to win the game and next two as well.

The troubled Moore would have problems that went far beyond one pitch. Three years later, he shot himself dead.

Also considered: The 1995 plunge and 2011 Albert Pujols contract.

16. San Diego Padres: San Diego Stadium-Jack Murphy Stadium Misconfiguration

San Diego Padres game at Jack Murphy Stadium

Years: 1969-present (53 seasons)

World Series championships: 0

Bottom Line: San Diego Stadium-Jack Murphy Stadium Misconfiguration

Expansion teams almost always suck, but they shouldn’t be as bor-ring as this one for so many years.

The Murph set the tone with its far-out dimensions — 375 feet to the power alleys and 420 feet to center field with an 18-foot-high wall from foul line to foul line. It wasn't just the home of the Padres. The San Diego Chargers and San Diego State Aztecs also called it home, and the multipurpose stadium also hosted myriad other events and concerts.

But it wasn't all fun and games and tailgates in the massive parking lot. Really, what free-agent slugger in his drug-free mind would have wanted to play there?

Also considered: The Ozzie Smith-for-Garry Templeton trade.

15. Seattle Mariners: Failed Glory Days in the Late 1990s-Early 2000s

Years: 1977-present (45 seasons)

World Series championships: 0

Bottom Line: Failed Glory Days in the Late 1990s-Early 2000s

Seattle Mariners shortstop Alex Rodriguez leaps out of way of Detroit Tigers runner Chris Gomez

In their prime (1996-2003), the M’s boasted a loaded lineup that featured some combination of Ken Griffey Jr., Edgar Martinez, Alex Rodriguez and Ichiro Suzuki, all Hall of Famer talents.

They also were wasted years to a large extent. The team failed to win more than two playoff games in any of them. Pin the tail on general managers Woody Woodward and Stand Pat Gillick, who failed to assemble more than mediocre staffs that consistently came up short when the stakes were highest.

14. Chicago Cubs: 1969 Meltdown

Black cat in front of 1969 Chicago Cubs dugout

Years: 1876-present (146 seasons, started as Chicago White Stockings/Colts/Orphans)

World Series championships: 3 (1907, 1908, 2016)

Bottom Line: 1969 Meltdown

So much suckage, so little space.

Decades later, the 1969 collapse remains near and dear to the hearts of longtime Cubs fans everywhere. Hey, it’s not often that a team blows a nine-game lead in the last six weeks of the season, you know.

Oh, and there’s the Lou Brock trade (1964), the Greg Maddux disaster (1992), the Leon Durham error (1984 NLCS), the Alex Gonzalez error (2003 NLCS), the list is long and undistinguished.

13. Philadelphia Phillies:1964 Collapse

Years: 1883-present (139 seasons, started as Philadelphia Quakers)

World Series championships: 2 (1980, 2008)

Bottom Line: 1964 Collapse

On Sept. 25, 1964, with the Phillies in first place but fading rapidly, manager Gene Mauch called on co-aces Chris Short and Jim Bunning to start four of the next six games on two days' rest.

The club dropped all six to cap an epic 10-game free fall that would haunt the franchise for years and Mauch for the rest of his life.

12. Atlanta Braves: Franchise Move From Milwaukee

Milwaukee County Stadium for 1957 World Series game between the Milwaukee Braves and New York Yankees

Years: 1876-present (146 seasons, started as Boston Red Stockings/Beaneaters/Doves/Braves/Bees, Milwaukee Braves)

World Series championships: 4 (1914, 1957, 1995, 2021)

Bottom Line: Atlanta Braves: Franchise Move From Milwaukee

Ronald Acuna Jr. in 1974 Atlanta Braves throwback uniform

When the team pulled up stakes in Milwaukee because of a crummy local television contract, so ended one of the greatest love affairs in team sports history. Hotlanta?

Before winning the 2021 World Series, the Braves had started to feel like little more than filler between football seasons there.

Maybe that will change now, and Atlanta might start a new love affair.

Honorable mention: The Lonnie Smith brain freeze in Game 7 of the 1991 World Series.

11. New York Yankees: Columbia Broadcast System Sale

Years: 1903-present (119 seasons, started as New York Highlanders)

World Series championships: 27 (1923, 1927, 1928, 1932, 1936, 1937, 1938, 1939, 1941, 1943, 1947, 1949, 1950, 1951, 1952, 1953, 1956, 1958, 1961, 1962, 1977, 1978, 1996, 1998, 1999, 2000, 2009)

Bottom Line: Columbia Broadcast System Sale

After a successful 19-year run, Dan Topping and Del Webb sold a 90 percent share of the Yankees franchise to CBS late in the 1964 season.

The next eight years were the worst extended stretch in club history. The team won 49 percent of its games, finished higher than fourth only once and watched the crosstown Mets take over the market.

Worse yet, the franchise was sold to a group headed by George Steinbrenner for $10 million, 24 percent less than the original price.

10. Oakland Athletics: Stadium Issue

Reggie Jackson with fans at the Oakland Coliseum in 1969

Years: 1901-present (121 seasons, started as Philadelphia/Kansas City Athletics)

World Series championships: 9 (1910, 1911, 1913, 1929, 1930, 1972, 1973, 1974, 1989)

Bottom Line: Stadium Issue

The Golden Seals. The Warriors. The Raiduhs. Oaktown is the place where sports franchises go to die, and the A’s are the last team standing.

The organization has made noises about a move for decades, but they turned out to be so much warm air.

So it remains stuck in a football stadium with thousands of tarp-covered seats that blot out what had been among the more scenic views in baseball.

9. Colorado Rockies: Coors Field Conundrum

Years: 1993-present (29 seasons)

World Series championships: 0

Bottom Line: Coors Field Conundrum

Larry Walker, Don Baylor, Dante Bichette, Vinny Castilla

The rarified air of Coors Field has produced grossly distorted offensive numbers, one-dimensional Rockies teams that haven’t won jack and a reason for any sane free-agent pitcher to stay away from the place.

As Los Angeles Dodgers broadcaster Vin Scully once put it, "You don’t need an official scorer at Coors Field. You need a certified public accountant."

Move home plate back another 10 feet and raise the fences five more. Problem alleviated.

Runner-up: The No. 2 pick of the 2006 draft (pitcher Greg Reynolds over Tim Lincecum, Clayton Kershaw and Max Scherzer among others.)

8. Pittsburgh Pirates: Bob Nutting Sale

Years: 1882-present (140 seasons, started as Pittsburgh Alleghenys)

World Series championships: 5 (1909, 1925, 1960, 1971, 1979)

Bottom Line: Bob Nutting Sale

Pittsburgh had a major league baseball team not that long ago, we troll you not. Then the team was sold to the Bob Nutting family after the 2006 season.

It wasn’t long before The Hillbilly Prince turned The 'Burgh into Hockeytown despite its jewel of a ballpark.

Next in line: The 1992 departure of free agent Barry Bonds that fetched nothing in return.

7. Florida-Miami Marlins: Jeffrey Loria Grand Theft

Years: 1993-present (29 seasons)

World Series championships: 2 (1997, 2003)

Bottom Line: Jeffrey Loria Grand Theft

There would be a major league team in Montreal had LaBatt Stadium been built. When the project was scrapped in 2002, Expos team owner-con man-thief Jeffrey Loria was able to sell the franchise to Major League Baseball, which moved it to Washington, D.C.

In turn, Loria was allowed to purchase the Marlins, who he used to bilk Miami and its taxpayers for hundreds of millions of dollars. He inherited a talented, young team that won it all the next year, not because of him but in spite of him.

6. Cincinnati Reds: Pete Rose Scandal

Years: 1882-present (140 seasons, started as Cincinnati Red Stockings, also Cincinnati Redlegs)

World Series championships: 5 (1919, 1940, 1975-76, 1990)

Bottom Line: Pete Rose Scandal

Team management claimed to have no clue that Charlie Hustle bet extensively on Reds games in the 1985-87 seasons. He was only their manager.

It took an MLB investigation to confirm as much two years later. Result: The unrepentant all-time hits leader still doesn’t have a Hall of Fame plaque, and the franchise remains scarred forever.

Nos. 2 and 2a: The Christy Mathewson and Frank Robinson trades.

5. St. Louis Cardinals: Curt Flood Misplay

Years: 1882-present (140 seasons)

World Series championships: 11 (1926, 1931, 1934, 1942, 1944, 1946, 1964, 1967, 1982, 2006, 2011)

Bottom Line: Curt Flood Misplay

Follow along here.

In Game 7 of the 1968 World Series Curt, Flood made one false step on a long drive to center field, which sailed over his head for a two-run triple, which ultimately allowed the Detroit Tigers to win the decisive game, which played a role in his salary dispute with team management only days later, which traded him to the Philadelphia Phillies the next year, which led to his unsuccessful court challenge of the reserve clause, which an independent arbitrator overturned eight years later, which allowed for the rampant free agency that exists today.

Rarely has one sequence set off a chain reaction that would have such an enormous effect on the game and its players.

4. Houston Astros: Signgate Scandal

Years: 1962-present (60 seasons, started as Houston Colt .45s)

World Series championships: 1 (2017)

Bottom Line: Signgate Scandal

The Astros cheated their way to the 2017 World Series title. That much we know. Fact is, more than one organization would sell their souls for one, especially at a time when ethics are optional.

We bet virtually everyone in H-town would agree that the ugly ordeal was worth every stolen sign of it. Nonetheless, the scandal ranks with the 1919 World Series fix and the steroids era as the worst in baseball history.

The franchise will be scarred forever because of it.

3. San Francisco Giants: Barry Bonds Travesty

Barry Bonds raises arms after hitting a home run

Years: 1883-present (139 seasons, started as New York Gothams/Giants)

World Series championships: 8 (1905, 1921, 1922, 1933, 1954, 2010, 2012, 2014)

Bottom Line: Barry Bonds Travesty

It wasn’t just that Barry, Barry Quite Contrary made an utter joke of the game and its history that was so reprehensible.

That head enabler Dusty Baker and the rest of the co-conspirators allowed the steroids travesty to happen was as bad if not worse.

Decades later, major league baseball still hasn’t recovered.

2. Boston Red Sox: Babe Ruth Sale

Years: 1901-present (121 seasons, started as Boston Americans)

World Series championships: 9 (1903, 1912, 1915, 1916, 1918, 2004, 2007, 2013, 2018)

Bottom Line: Babe Ruth Sale

In the 1919 season, The Bambino hit more home runs (29) than 10 of the 16 major league teams. So why would the temperamental pitcher-outfielder be sold only weeks later, a monumental transaction whose effects are still felt one century later?

Red Sox owner-Broadway producer H. Harrison (Harry) Frazee was a desperate soul at the time, so rather than meet Ruth’s salary demands, he unloaded his most valuable asset for a then-record $100,000 in return.

The Yankees went on to win four World Series in the next 13 seasons, while the Red Sox didn’t finish over .500 in any of them. Not coincidentally, soon New Yawk replaced Bahston as the most relevant city in the country.

Next worst: The 1911 collapse, the 1978 collapse and the 2011 collapse, not necessarily in that order.

1. Chicago White Sox: Black Sox Scandal

Years: 1901-present (121 seasons)

World Series championships: 3 (1906, 1917, 2005)

Bottom Line: Black Sox Scandal

Judge Kenesaw Mountain Landis, rear left, talks Chicago White Sox players in 1921

This juggernaut was on a brink of a dynasty in the 1919 season, when disgruntled superstar Shoeless Joe Jackson and seven co-conspirators either took part or had knowledge of the fix of the World Series.

It remains the greatest scandal in pro team sports history, one that has permanently scarred a franchise and the game.

Let’s not forget the role of team owner Charles Comiskey here. If the devious tightwad had taken better care of his players, the sordid ordeal might have been on a smaller scale, if it happened at all.