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This ranking explores and orders the most regrettable events in the history of American professional baseball, moments overshadowed by human mistakes and unfortunate twists of fate. Share your personal picks in the comments section as usual.
10. The Infamous Pine Tar Incident
There’s something oddly captivating about witnessing someone lose their temper. On July 24, 1983, during a game between the Kansas City Royals and the Yankees, Royals’ George Brett lived out every child’s fantasy by hitting a game-changing home run in the 9th inning. His two-run shot gave the Royals a 5-4 lead. However, as Brett celebrated and headed to the dugout, Yankees manager Billy Martin pointed out to home plate umpire Tim McClelland that Brett’s bat might have exceeded the allowed 18 inches of pine tar on the handle.
According to the rules, a bat cannot have more than 18 inches of any substance applied to it. After measuring the bat against the 17-inch-wide end of home plate, the umpires concluded that Brett had violated the rule. McClelland located Brett in the dugout and signaled that he was out. The entire incident was televised and is available on YouTube.
Brett erupted from the dugout in a furious rage, his face flushed with anger, shouting expletives and threatening McClelland. Royals manager Dick Howser and several teammates had to physically restrain him to prevent an altercation. McClelland nullified the home run and declared the game over, awarding the victory to the Yankees.
A commentator humorously remarked, 'Brett has made history as the first player to hit a home run that lost the game.' The Royals challenged the decision, and it was reversed. While an illegal bat typically results in an out, the pine tar did not enhance the ball's distance, so Brett's home run stood. The game resumed from that point, and the Royals ultimately won 5-4. However, Brett's outburst set a poor example for his younger fans.
9. George Steinbrenner
Steinbrenner served as the principal owner of the New York Yankees from 1973 until his passing in 2010 at 80 years old. Over his 37-year tenure, he managed to earn the disdain of players, coaches, assistant managers, and fans alike. Known as “the Boss,” a nickname he shared with Josef Stalin among Soviet circles, Steinbrenner was notorious for his authoritarian style.
One of his more absurd demands was enforcing strict grooming standards, requiring players to shave their beards and maintain military-style haircuts during the 70s and 80s, a time when long hair was fashionable. Players were permitted only thin mustaches. On one occasion, he instructed coach Yogi Berra to tell Goose Gossage to shave his beard. Berra, who despised Steinbrenner, repeatedly stated that his loyalty was to the team, not the money. When Steinbrenner offered him a raise, Berra sarcastically replied, “Yeah. Sure.”
Gossage defied the order by styling his mustache like Hulk Hogan, which also violated Steinbrenner’s rules. Steinbrenner even benched Don Mattingly, one of the Yankees’ top players at the time, for refusing to trim his mullet. After backlash from teammates and fans, Steinbrenner eventually backed down.
At a prestigious baseball banquet, Steinbrenner encountered legendary pitcher Tom Seaver, who openly criticized him to his face. Steinbrenner lost his temper and threatened to fire Seaver on the spot, only for Seaver to retort, “I play for the Mets, George.” Steinbrenner stormed off in frustration.
Steinbrenner appeared to take pleasure in firing people, dismissing managers over 20 times. The most infamous case was Billy Martin, whom he fired and rehired five times. Martin’s dismissals were often due to his candid criticism of Steinbrenner, who retaliated by terminating him repeatedly. This behavior created a toxic reputation across the MLB, where even a single misstep could cost someone their job, as pleasing Steinbrenner was nearly impossible.
8. Juan Marichal vs. John Roseboro
When it comes to bench-clearing brawls, few incidents in professional baseball history match the sheer intensity and disgrace of the infamous clash between Juan Antonio Marichal Sanchez and John Junior Roseboro on August 22, 1965. Marichal, a pitcher for the San Francisco Giants, faced off against Roseboro, the catcher for the Los Angeles Dodgers, in a game between two long-standing rivals.
In the first three innings, Marichal intentionally threw pitches dangerously close to lead-off hitter Maury Wills’s head, forcing him to duck. This was clearly meant to provoke. When Marichal came up to bat in the bottom of the 3rd, Roseboro began taunting him. Already frustrated by being outperformed by Dodgers pitcher Sandy Koufax, Marichal exchanged heated words with Roseboro. The tension escalated when Roseboro started throwing Koufax’s pitches back dangerously close to Marichal’s head.
The situation exploded when Roseboro stood up and confronted Marichal face-to-face, shouting at him. In response, Marichal stepped back and struck Roseboro three times with his bat, knocking him to the ground and causing a severe scalp injury that required 14 stitches. The incident triggered a massive 15-minute brawl at home plate. Giants’ Willie Mays assisted Roseboro back to the dugout, while Koufax attempted to restore order. The most iconic image from the fight captures Marichal with his bat raised high and Roseboro collapsing at his feet.
Marichal received a mere 9-day suspension and a $1,750 fine, a penalty many critics considered too lenient. Roseboro healed completely and, surprisingly, the two eventually became friends.
7. Pete Rose Bets on Himself
Rose spent his career with the Cincinnati Reds from 1963 to 1986, amassing a record-breaking 4,256 hits, the most in MLB history. Ty Cobb had held the previous record with 4,191 hits for 57 years (Rose had 2,624 more at-bats). To this day, they remain the only players to surpass 4,000 hits. Known as “Charlie Hustle,” Rose was one of the greatest contact hitters ever, consistently making contact with the ball without relying on home run power. Cobb, too, was a legendary figure in the sport.
Rose was an exceptional all-around player, excelling as a first, second, and third baseman, as well as a left and right fielder. His nickname reflected his aggressive base running and relentless drive to win. Throughout his career, he often gambled on himself and his team to win, never betting against them, as that would have been equivalent to game-fixing. Confident in his team’s abilities, he saw it as a way to earn extra money without harming anyone.
The issue was that Rose was fully aware his actions violated MLB regulations and that exposure would lead to severe repercussions. When suspicions arose, he chose to lie. Many fans admit that his dishonesty is their only grievance with him. His reputation took another hit in 1990 when he pleaded guilty to income tax evasion, resulting in prison time and bringing his gambling addiction into the public eye. It wasn’t until 2004 that he finally admitted the truth, a delay that many felt insulted their intelligence.
Despite this, MLB and the Hall of Fame voting committee face criticism for continuing to exclude such an extraordinary talent. Their refusal to forgive tarnishes the spirit of the game, much like Rose’s actions did. The Hall of Fame, meant to celebrate talent and legacy, is diminished by this exclusion. Like the Academy Awards, it should focus solely on performance, free from politics or personal biases. However, as with any voting system, human grudges can influence decisions.
6. Ty Cobb Beats up a Fan
No list of baseball controversies would be complete without Ty Cobb. Arguably one of the greatest players of all time, Cobb still holds several records a century later, including the highest career batting average (.367) and the most batting titles (12). He scored 4,191 runs and stole home 54 times, often with his sharpened cleats aimed at the catcher’s face. However, Cobb’s personality was deeply flawed. Known for his violent temper and racist behavior, he once assaulted a black elevator operator for talking back and even stabbed a black constable who tried to intervene.
On one occasion, Cobb violently attacked the Detroit Tigers’ groundskeeper, knocking out his teeth for failing to smooth the infield before a game. When the groundskeeper’s wife intervened, Cobb placed her in a chokehold. In another incident, Cobb and umpire Billy Evans agreed to settle a heated, profanity-laden argument with a fistfight after a game. Cobb won by kicking Evans in the groin, pinning him down, and repeatedly punching him.
Cobb’s most infamous moment came on May 15, 1912, when a heckler named Claude Lueker relentlessly taunted him for six innings. Cobb initially tried to ignore the insults, even asking the opposing manager and two police officers to remove Lueker, but no action was taken. The situation escalated when Lueker shouted a racial slur at Cobb as he returned to the dugout.
Without hesitation, Cobb threw his hat into the dugout and climbed into the stands. Lueker, who was disabled due to an industrial accident that left him with only one hand and three fingers, was defenseless. Cobb punched him in the face, and when the crowd protested that Lueker had no hands, Cobb retorted, “I don’t care if he has no feet!” He continued beating Lueker until his teammates pulled him away.
Cobb was suspended for the remainder of the season, and his teammates boycotted the next game in solidarity. Eventually, Cobb convinced them to continue playing. Lueker was hospitalized with a broken jaw and nose.
5. Black Sox Scandal
For baseball enthusiasts, the 1919 World Series needs no introduction. However, for those unfamiliar, the series pitted the Chicago White Sox, later dubbed the “Black Sox,” against the Cincinnati Reds. The White Sox were owned by Charles Comiskey, a domineering figure who treated his players as mere property. His behavior made Ty Cobb seem saintly in comparison. Comiskey, like other owners, had complete control over player salaries under the MLB Reserve Clause, leaving players powerless.
Comiskey had promised pitcher Eddie Cicotte a $10,000 bonus for winning 30 games. However, when Cicotte reached 28 wins, Comiskey benched him for the remainder of the season to avoid paying. Similarly, Comiskey promised the team a bonus for winning the 1919 pennant, only to reward them with a case of flat champagne. He even forced players to cover their own uniform laundry expenses.
Comiskey’s mistreatment drove at least six players to conspire to intentionally lose the 1919 World Series as retribution. The involved players were Eddie Cicotte, Arnold Gandil, Charles Risberg, Fred McMullin, Oscar Felsch, and Claude Williams. These six, along with George Weaver and “Shoeless” Joe Jackson, were banned from professional baseball for life. Weaver and Jackson were accused of being aware of the fix but failing to intervene.
Modern perspectives have softened toward Weaver and especially Jackson. Jackson, who was illiterate, had no direct involvement in the fix and likely only suspected wrongdoing after witnessing the conspirators’ blatant errors. Weaver knew about the scheme but chose not to betray his teammates. Both played exceptionally well during the series. Jackson is now celebrated as one of the greatest hitters in history, ranking third in career batting average at .356. In his 1911 rookie season, he hit an impressive .408.
The Reds clinched the series 5-3, which at the time was a best-of-nine format. The conspirators, though skilled players, were unconvincing in their attempts to lose intentionally. Their poor performance was so obvious that even the batboys noticed something was off. In the first game, Cicotte, a star pitcher, inexplicably allowed five runs in the fourth inning, raising immediate suspicions. The White Sox lost the game 9-1, an embarrassing result for such a talented team.
They also lost the second game. However, rookie pitcher Dickie Kerr redeemed the team by pitching a shutout in the third game, proving he wasn’t involved in the fix. In the fourth game, Jackson attempted to throw a runner out at home, but Cicotte intentionally mishandled the ball, allowing the run. Despite the scandal, Jackson hit an impressive .375 during the series. By the end, the games were met with more boos than cheers. If not for the emergence of Babe Ruth the following year, baseball might have suffered irreparable damage. The eight players involved remain barred from the Hall of Fame.
4. Sandy Koufax Throws His Arm Away
One of the most tragic endings to what could have been the greatest pitching career in baseball history was Sandy Koufax’s early retirement due to crippling arthritis. Over his 12-year career with the Brooklyn and Los Angeles Dodgers, Koufax amassed 2,396 strikeouts and maintained a career ERA of 2.76, the second-lowest in the live-ball era. His untimely departure left fans wondering what more he could have achieved.
Koufax’s peak years were 1965 and 1966. Despite enduring excruciating pain in his left elbow, he consistently pitched complete games. One morning, he awoke to find his arm bruised from shoulder to wrist due to internal bleeding. To manage the pain, he relied on Empirin with codeine, Butazolidin, and capsaicin cream, while soaking his arm in ice after every game.
Despite his suffering, Koufax continued to pitch complete games day after day. On September 9, 1965, he achieved a perfect game, a feat rarer than orbiting the Moon. A perfect game requires no hits, walks, or base runners, and Koufax struck out 14 of the 27 batters he faced, setting a record for the most strikeouts in a perfect game.
Koufax’s pitching was legendary. Carl Yastrzemski, a hitter with 3,419 career hits, once said, “Trying to hit Koufax’s curveball was like trying to drink coffee with a fork.” Koufax’s over-the-top delivery, combined with his powerful legs, gave his pitches incredible speed. His curveball, clocked at 94 mph, dropped sharply in the final moments, forcing batters to swing awkwardly as if hitting a golf ball.
His four-seam fastball had a unique upward movement, floating up to four times before reaching the catcher. Despite the severe pain in his arm, Koufax began unintentionally tipping his pitches, revealing what he was about to throw. Yet, as Willie Mays noted, “Even knowing what was coming, I still couldn’t hit him.”
By the end of 1966, with a 1.73 ERA, Koufax retired due to unbearable pain that disrupted his sleep and even made him consider amputation. Remarkably, his arm healed quickly once he stopped pitching. Jeff Torborg, who caught his perfect game, once said, “It was as if God reclaimed his arm.”
3. Lou Gehrig’s Disease
Lou Gehrig often found himself overshadowed by Babe Ruth as a power hitter. However, Gehrig’s breakthrough came in 1926, his third professional season, where he achieved 20 triples, 47 doubles, 16 home runs, 116 RBIs, and a .313 batting average. While Ruth outperformed him in home runs and batting average, Gehrig proved his prowess the following year, solidifying his place among the elite power hitters.
The 1927 Yankees are widely regarded as the greatest baseball team in history. Ruth set a record with 60 home runs, but Gehrig surpassed him with 175 RBIs, an impressive feat given that Gehrig batted fourth, often with the bases cleared by Ruth. The team’s lineup, known as “Murderers’ Row,” included Earle Combs, Mark Koenig, Babe Ruth, Lou Gehrig, Bob Meusel, and Tony Lazzeri.
Combs and Koenig were exceptional contact hitters, frequently setting the stage for Ruth and Gehrig. Gehrig’s position as the cleanup hitter contributed to his record 23 career grand slams. That season, he led the team with a .373 batting average, outperforming Ruth and Combs, who both hit .356.
As Gehrig’s career progressed, the legendary first baseman, often hailed as the best in history, began struggling with simple plays at first base. Once known for his lightning-fast base running, he now moved sluggishly and stumbled awkwardly. By late 1938, his hitting power had noticeably declined. While he could still make contact, his ability to hit home runs had significantly diminished.
Unlike his friend Babe Ruth, who had retired after a life of indulgence, Gehrig was known for his disciplined lifestyle. By April 1939, his performance hit an all-time low, with a .143 batting average and just one RBI. Observers noted that while he was still connecting with the ball, it lacked the usual power and distance.
On May 2, 1939, Gehrig ended his streak of 2,130 consecutive games, a record that stood until 1995. He approached his coach and said, “I’m benching myself, Joe.” Recognizing he was no longer contributing to the team, he made the difficult decision to step aside.
Gehrig and his wife traveled to the Mayo Clinic, where, after six days of tests, Dr. Charles Mayo delivered the devastating diagnosis: amyotrophic lateral sclerosis (ALS). The disease gradually erodes the brain’s ability to control muscles, leaving the victim increasingly weak and immobile while the mind remains unaffected. For an athlete, the lack of pain made the decline even more perplexing.
Gehrig’s farewell on July 4, 1939, during a doubleheader, is remembered as one of the most poignant moments in baseball history. Surrounded by teammates, rivals, and fans, he was overwhelmed with gifts but could barely hold them due to his weakened state. The scene remains a testament to his enduring legacy and the heartbreaking nature of his condition.
Following a brief speech by Babe Ruth, Gehrig spoke to the 61,808 fans at Yankee Stadium, declaring himself “the luckiest man on the face of the earth” and urging them not to pity him. His number 4 jersey became the first in MLB history to be retired. Later that year, at 36, he was the youngest player inducted into the Hall of Fame, a record later surpassed by Sandy Koufax. In 1999, he received the most votes for the All-Century Dream Team.
Gehrig passed away on June 2, 1941, at his home, succumbing to asphyxia caused by the paralysis of his diaphragm and abdominal muscles. Many analysts believe that had his career spanned 20-25 years instead of 16, he might have eclipsed many of Babe Ruth’s records.
2. Christy Mathewson Gets Gassed
Mathewson stands as one of the greatest pitchers in baseball history, excelling during the dead ball era when a single ball was used for entire games. These balls became hard to see after being dirtied and spit-covered (spitballs were legal until 1921). While Mathewson occasionally used the spitball, he was celebrated as a “control pitcher,” contrasting with power pitchers like Nolan Ryan. Ryan’s 100+ mph fastball was legendary, but he lacked the precision and versatility that defined Mathewson’s pitching.
Mathewson’s pitching arsenal was unmatched. He could deliver strikes with a variety of pitches: the 2-seam and 4-seam fastballs, forkball, slider, sinker, curveball, knuckleball, knuckle-curve, palmball, palm-curve, and his signature screwball, which curved opposite to a traditional curveball. His precision allowed him to dominate batters with ease.
While Nolan Ryan holds the record for the most career strikeouts at 5,714, he also leads in walks with 2,795, meaning he walked nearly half the batters he faced. In contrast, Mathewson struck out 2,507 batters and walked only 848, a rate of 33%. This stark difference highlights Mathewson’s exceptional control and accuracy, earning him the nickname “the Christian Gentleman.”
Tragically, Mathewson’s career was cut short when he enlisted in WWI in 1918 as a chemical weapons instructor. Alongside Ty Cobb and George Sisler, he trained soldiers in France. As a captain, his role involved overseeing gas chamber exercises, where soldiers practiced using gas masks during controlled mustard gas releases.
During one exercise, a miscommunication led to the premature release of gas. Mathewson prioritized the soldiers’ safety, ensuring they secured their masks before calling for the gas to be shut off. However, the delay caused him to inhale the gas, as he couldn’t hold his breath long enough. When a private attempted to remove his mask, Mathewson, despite his own peril, stopped him and ordered him to stay still.
That single breath of gas gave Mathewson tuberculosis. After returning home, he attempted to coach but required frequent breaks for his health. He retired in 1921 and passed away four years later at 45. His teammates mourned deeply, with many weeping openly at the first game after his death.
1. Steroids
A common refrain during the steroid scandal is, “Babe Ruth did it on hotdogs and beer.” Many fans dislike seeing long-standing records broken, especially iconic ones like Ruth’s 60 home runs in a season. Roger Maris surpassed it by one in 1961, but in 1998, Mark McGwire and Sammy Sosa both shattered the record, with McGwire hitting 70 and Sosa 66.
The idea that two players could break such a revered record simultaneously seemed unbelievable. Sosa’s career took a hit when he was caught using a corked bat, which allegedly increases swing speed. In 2005, the steroid scandal exploded, leading Congress to subpoena McGwire, Jose Canseco, and Rafael Palmeiro. Sosa was linked to steroid use, Canseco admitted to using and supplying them, and Palmeiro denied usage only to be caught months later. McGwire initially refused to answer questions but later admitted to using steroids to recover from injuries, though he denied they boosted his home runs—a claim widely disputed.
The scandal’s shadow lingers, as records set during the steroid era remain intact. Barry Bonds, who holds both the single-season (73) and career (762) home run records, was convicted of obstructing justice in the scandal and is widely suspected of steroid use. Despite his achievements, the San Francisco Giants declined to renew his contract, and no other team signed him, reflecting public disdain for his tainted legacy.
