In this episode of Conspiracy Theories, the hosts examine allegations that tennis legend Bobby Riggs may have intentionally lost the 1973 "Battle of the Sexes" match against Billie Jean King. The episode explores Riggs's history as a hustler and gambler, including his connections to organized crime figures and substantial gambling debts. Investigative journalist Don Van Natta Jr.'s research uncovered eyewitness accounts of mobsters discussing a potential fix, while Riggs's behavior before and during the match raised questions about his preparation and performance.
The episode also addresses the match's broader significance for the women's liberation movement and whether evidence of a fix would diminish King's legacy. While the circumstantial case for Riggs throwing the match includes mob connections, suspicious behavior, and inconsistent preparation, the theory remains unproven. The hosts consider how King's victory became a transformative cultural moment regardless of the truth behind these allegations, and examine the tension between athletic achievement and symbolic meaning in sports history.

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Bobby Riggs won his first tennis racket in a bet at age 11, quickly becoming a prodigy who reached the final of his first tournament. By 16, he had captured the US Junior Singles Championship and was barnstorming across the country to play adult amateurs. In 1939, Riggs placed an audacious bet on himself at 25-to-1 odds to win Wimbledon's men's singles, doubles, and mixed doubles—a feat he accomplished, earning the equivalent of about $2.6 million today.
As his tennis prime passed, Riggs mastered the art of hustling through a technique he called "staying in the barn," where he'd intentionally appear to struggle before storming back to win once opponents raised their wagers. His gambling expanded beyond tennis to high-stakes golf matches with Chicago mobsters, and despite his massive winnings, he squandered fortunes on horse racing, card games, and reckless bets—including losing a million-dollar divorce settlement in 1972.
In 1973, amid the women's liberation movement, Riggs adopted a provocative male chauvinist persona—though associates claimed it was largely performative—to challenge female tennis champions. He defeated Margaret Court 6-2, 6-1 on Mother's Day in a nationally televised match, earning $10,000 and using the platform to taunt Billie Jean King into a match "as long as the price is right."
Investigative journalist Don Van Natta Jr. received a tip about Hal Shaw, an assistant golf pro who witnessed a late-night meeting in 1972 or 1973 at a Tampa golf club. Shaw saw notorious mobsters—including Santo Trafficante and Carlos Marcello—discussing Bobby Riggs's proposal: Riggs, who owed them about $100,000 in gambling debts, would beat Margaret Court but intentionally lose to Billie Jean King. In exchange, his debts would be cleared and money placed in an English bank account. The mobsters assigned a Chicago associate to oversee the fix.
Van Natta verified Shaw's credibility by having him repeat the story multiple times with consistent details. Larry Riggs, Bobby's son, recalled Chicago mobsters visiting his father in the weeks before the Battle of the Sexes, including Jackie "the Lackey" Cerrone. When Larry questioned these visits, Bobby brushed him off, saying he had "some business with them." Larry also noted his father didn't train seriously for King, unlike his intense preparation for Court.
However, Lornie Kuehl, Bobby's friend and executor, adamantly denied the mob-fixing story, insisting Bobby never owed the mob money and no English bank account existed. While the evidence of Riggs's mob ties, gambling debts, and suspicious circumstances is substantial and suggestive, it remains unproven, leaving both the possibility of a fixed match and innocent explanations on the table.
Van Natta points out that in 1973, women still needed a man's signature to get a credit card, underscoring the inequality that made the Battle of the Sexes more than just sport. Bobby Riggs campaigned publicly to "put Billie Jean and all other women's libbers back where they belong, in the kitchen and the bedroom," while Billie Jean King understood that defeat could "set us back 50 years" in the fight for equal opportunities and respect for women.
King, already a celebrated champion with 10 major singles titles, had recently forced the US Open to offer equal prize money by threatening not to play unless the disparity was corrected. She also spearheaded the formation of the Women's Tennis Association in 1973 and prepared rigorously for the Riggs match, viewing the outcome as pivotal for women in sports and society.
On September 20, 1973, over 30,000 people filled the Houston Astrodome and 50 million Americans watched on television as Riggs entered on a throne and King arrived in a feathered chariot. King defeated Riggs convincingly 6-4, 6-3, 6-3, delivering a powerful win for the women's liberation movement and solidifying herself as a feminist icon. Her victory showed decisively that women could compete at the highest levels and struck a blow against those who tried to confine women to traditional roles.
Leading up to the match, Bobby appeared overweight, sluggish, and spent the night before drinking and partying with women—behavior wildly uncharacteristic for such a major event. On match day, he looked slow, made unforced errors, missed nearly half his first serves, and double faulted at critical moments. His normally reliable technical game faltered, and his demeanor was morose, prompting one voice in the crowd to shout that Bobby had bet on Billie Jean.
Bobby's son Larry grew so frustrated with his father's unconcerned attitude that he refused to accompany him to Houston, warning he would embarrass himself. Hours before the match, Bobby practiced casually with a dog tied to his ankle and an umbrella, taking on challengers for $100 a game. This stood in stark contrast to his obsessive training for Margaret Court, raising unexplained questions about his motivations.
Billie Jean King, however, was adamant that Bobby tried to win, asserting his poor play stemmed from nerves or lack of preparation, not intent to lose. She maintained she saw genuine will to win in his eyes and said she would bet her life that Bobby never discussed throwing the match with mobsters, reasoning he had every incentive to win for more lucrative future matches.
Bobby's behavior after the loss was ambiguous. He called himself "the biggest bum of all time" and immediately requested a rematch. That night, sitting in an ice bath, he told his son that losing to Billie Jean was "the worst thing I've ever done"—words that could reflect genuine defeat or guilt over throwing the match. A year before his death, Bobby insisted, "Billie Jean beat me fair and square," but in a final call with King, he remarked cryptically, "We did it, didn't we? We really made history"—a comment that could signify shared pride or, as some speculate, a veiled reference to alleged collusion.
Billie Jean King's legacy as a pioneer for women's equality stands independent of any controversy. Life magazine listed her among the 100 most important Americans of the 20th century, and she has won 12 major singles titles, founded the Women's Tennis Association, championed equal rights and LGBTQ causes, and received the Presidential Medal of Freedom. The U.S. Open is played annually at the Billie Jean King National Tennis Center. Martina Navratilova called King a "crusader for all" who will always be the hero of this story, emphasizing that her cultural impact extends well beyond a single match outcome.
Van Natta argues that even if Bobby threw the match, Billie Jean's achievement remains undiminished. The cultural impact of the Battle of the Sexes—how it made people feel and the shift it provoked—cannot be erased regardless of Riggs's intentions. King trained rigorously, performed at the highest level, endured enormous pressure, and emerged victorious with ease, becoming a feminist icon and American hero. Van Natta acknowledges he has constructed a "pretty strong" circumstantial case but has not proven the fix theory beyond doubt, offering an intriguing possible alternative history while recognizing room for the match's legitimacy.
The match exists at the intersection of literal athletic achievement and symbolic cultural spectacle. Regardless of Bobby Riggs's true intentions, Billie Jean King's intensive preparation and tactical excellence showcased real athleticism, and her victory witnessed by 80 million viewers was a transformative moment for gender equality. The enduring tension between factual truth and monumental cultural meaning underscores that King's triumph fueled progress and remains a beacon for equal rights in sports and beyond.
1-Page Summary
At age 11, Bobby Riggs wins his first tennis racket in a bet. He picks up the sport quickly, displaying prodigious talent by reaching the final of the first tournament he enters. From the outset, Bobby marks himself as a tennis prodigy with a natural knack for competition and risk.
By 16, Bobby captures the US Junior Singles Championship. Never content to rest, he crisscrosses the country in his car as a teenager, barnstorming to play matches against adult amateurs nationwide. Despite setbacks like having his clothes and wallet stolen, Bobby perseveres and continues to chase success wherever he can find it.
In June 1939, Bobby reaches the final of the French Open, soon discovering that bookmakers in London have set 25-to-1 odds on him winning Wimbledon. Seizing the opportunity, Bobby places an audacious bet on himself, requiring him to win men's singles, doubles, and mixed doubles. That July, he accomplishes the feat at Wimbledon, pocketing $108,000 in gambling winnings, the equivalent of about $2.6 million today. His blend of skill, bravado, and risk-taking solidifies his legend as much as his titles.
As his professional tennis prime passed, Bobby Riggs elevates his mastery as a manipulator and hustler. He becomes known for the technique he calls "staying in the barn," where he appears to struggle in a match, intentionally losing a set or two to coax his opponent into upping their wager. Once his opponent commits to a larger bet, Bobby abandons his ruse, storms back, and wins both the match and the stakes. Friends and observers often note if Bobby is "quite conspicuously keeping his game in the barn,” recognizing his gift for deception and gamesmanship.
Bobby’s hustle expands beyond tennis to high-stakes golf matches. He plays against notorious figures such as Jackie "the Lackey" Sarone, a Chicago mobster connected to Sam Giancana. During these games, Bobby's son Larry, who caddies for him, witnesses Sarone and his cohorts cheat by moving Bobby's ball. Bobby ignores the cheating, instructing his son that these are people you don't confront. Bobby’s penchant for action keeps him in the company of high stakes and sometimes dangerous individuals.
Despite his huge winnings, Bobby indulges a reckless, insatiable appetite for gambling. After earning a fortune betting on himself at Wimbledon, he quickly loses it at horse races and on gin rummy. In 1972, following a divorce, Bobby squanders a million-dollar settlement on cards, horse races, football, and his senior tennis matches, showing no inclination for prudent investment or lasting wealth.
Bobby Riggs' History as a Hustler and Showman
Investigative journalist Don Van Natta Jr. explores the longstanding suspicion that Bobby Riggs may have fixed the famous "Battle of the Sexes" tennis match against Billie Jean King, focusing on Riggs's deep ties to gambling and the American mob.
Don Van Natta Jr. received a confidential tip about Hal Shaw, an assistant golf pro in Tampa, Florida, who had kept a secret for decades. One late night in late 1972 or early 1973, Shaw was closing up at the Palma Sia Golf Club when he witnessed a meeting in the pro shop involving some of America's most notorious mobsters: Frank Regano, Santo Trafficante, and Carlos Carsello. Shaw recognized three of the four men present but not the fourth.
During the meeting, the mobsters openly discussed a proposal brought by Bobby Riggs, who they said owed them about $100,000 in gambling debts. Riggs, a notorious gambler who regularly bet on both sports he could and couldn't control, proposed setting up two exhibition matches in 1973: first beating Margaret Court and then, if he could arrange a match with Billie Jean King, intentionally losing to her. In return, Riggs wished for his debts to be erased and to have a sum placed in an English bank account. The mobsters were initially concerned whether enough betting action could be drawn from a tennis exhibition, but after agreeing to Riggs's scheme, they decided that one of their Chicago associates would oversee the fix to ensure Riggs would deliver on this promise.
The discussion included skepticism about engineering the fix and ensuring enough betting interest. Nevertheless, the Chicago connection was crucial: a mobster in Chicago would be responsible for orchestrating and monitoring the plan, highlighting the gravity of the operation from the mob’s perspective.
Van Natta met with Shaw and had him repeat the story multiple times, old detective-style, to check for consistency. Shaw recalled the details identically each time and demonstrated no apparent motive for fabrication. Shaw believed deeply that Bobby took a dive and made it look convincing, though he kept the story secret from everyone, including his family, for nearly 40 years.
Van Natta also spoke with Larry Riggs, Bobby’s son, and Lornie Kuehl, Bobby’s close friend and executor. Larry remembered connected mobsters from Chicago visiting Bobby in the weeks before the Battle of the Sexes, noting that Bobby frequently socialized and played cards or golf with such men, especially mobster Jackie "the Lackey" Cerrone from Chicago. Larry himself met Cerrone and recognized associates visiting Bobby prior to the match. Larry questioned his father about these men but was told, “I’ve got some business with them, don’t sweat it.”
Larry recalled a pattern of mobsters’ visits and admitted he never understood why several of them turned up right before the match. Larry knew Bobby’s connection with mob figures stretched back to the 1950s. He also found it strange that Bobby didn’t train hard for the match with Billie Jean King, unlike his intense preparation against Margaret Court. Larry theorized that if Bobby did throw the match, it might have been to secure a more lucrative rematch.
Mob Involvement and Connection to Bobby's Gambling Debts
Don Van Natta Jr. points out that in 1973, women still needed a man's signature to get a credit card—a vivid reminder of the legal and social inequality women faced. Against that background, the legendary tennis match between Billie Jean King and Bobby Riggs was more than just a sporting event; it represented a decisive battle in the ongoing fight for gender equality. Bobby Riggs publicly campaigned on the notion of male superiority, pledging to "put Billie Jean and all other women's libbers back where they belong, in the kitchen and the bedroom." Riggs wore the persona of the "male chauvinist pig," and his bombastic comments drew sharp lines between patriarchy and the rising women's liberation movement of the time.
Billie Jean King understood the existential stakes. She openly declared that defeat could "set us back 50 years," fearing that a loss would undermine progress toward equal opportunities, pay, and respect for women—not just in tennis, but in society at large. King believed the match had the potential to impact equal prize money, the formation of the Women's Tennis Association, and the broader social perception of women's capabilities.
Billie Jean King was already a celebrated champion with 10 major singles titles and five year-end number-one rankings. She had recently taken a courageous stand for equality after winning the 1972 US Open but receiving $15,000 less than the men’s champion. In response, she told organizers she wouldn't play the next year unless prize money was equal. Her threat worked—by 1973, the US Open became the first of the Grand Slam tournaments to offer equal pay.
As she championed better treatment for women players, King also spearheaded the formation of the Women's Tennis Association in 1973, launching it as a form of union for female athletes. Entering the Battle of the Sexes, Billie Jean King took her challenge seriously; she prepared rigorously, viewing the outcome as pivotal not just for her own career but for the trajectory of women in sports and beyond. Despite joking with her opponent, she trained as if her life depended on the match.
On September 20, 1973, over 30,000 people filled the Houston Astrodome—the largest crowd ever for a US tennis match. Across the nation, about 50 million Americans watched on television, marking an unprecedented level of attention to a sporting event and capturing the American public’s imagination. The match was as much entertainment as athletic contest: Bobby Riggs made his entrance on a ...
1973 Match's Significance For Women's Liberation Movement
The famed "Battle of the Sexes" match between Bobby Riggs and Billie Jean King has long attracted speculation about whether Bobby intentionally lost. Observers and those close to him noted several anomalies in his preparation and conduct that have fueled theories about his performance.
Leading up to the match, Bobby looked heavier than usual, sluggish, and seemed to care little about maintaining his typical competitive edge. The night before facing Billie Jean King, he was seen drinking and partying with several women. When questioned by Malloy about this uncharacteristic behavior before such a major event, Bobby confidently replied that there was no way Billie Jean could beat him.
On match day, Bobby's play was filled with errors. He looked slow, made unforced mistakes, and his normally reliable serve faltered—missing almost half of his first serves and double faulting during critical points. Some of his shots barely cleared the net, while others did not reach it at all. Journalist Don Van Natta Jr., upon reviewing the tape after hearing Hal Shaw’s gambling-related story, noticed that Bobby’s technical execution was markedly off compared to his usual standards. Throughout the match, Bobby’s demeanor was uncharacteristically morose; he failed to attack and appeared to mope around the Astrodome court. Friends wondered openly if he was holding back. During play, a voice in the crowd even shouted that Bobby had bet on Billie Jean.
Bobby's son Larry grew frustrated with his father's unconcerned attitude, so much so that he refused to accompany him to Houston, telling his father he would embarrass himself on national television.
Hours before the match, Bobby practiced at a nearby facility, not with intensity or focus, but with a dog tied to his ankle, an umbrella in one hand, and taking on challengers for $100 a game. This unserious approach baffled friends and family.
Observers who watched Bobby train obsessively for his prior match against Margaret Court noted that he showed no such dedication before facing Billie Jean. The contrast in preparation raised suspicions and fueled speculations about his true intentions for the King match, especially since it resulted in a subpar, lackluster performance unlike the dominant display he gave against Margaret Court.
Billie Jean King asserted that Bobby's poor play stemmed from nerves or lack of preparation, not an intent to lose. On court, even as Bobby failed to attack and seemed out of sorts, she maintained that she saw in his eyes a genuine will to win and was convinced that he did not throw the match.
In interviews, Billie Jean King was adamant in denying any fix, going as far as to say she would bet her life that Bobby had never spoken to mobsters about throwing the match. She reasoned that Bobby had every incentive to win, pointing out that victory would have set up even more lucrative games against other top women.
Billie Jean expressed incredulity at the idea of a fix, especially when told the details of purported mob involvement. Yet, even her certainty is tempered by external observations of Bobby's passive tactics and uncharacteristic errors, leaving some room for doubt about his intentions. ...
Investigation Into Whether Bobby Intentionally Threw Match
Billie Jean King's legacy as a pioneer for women's equality and tennis excellence stands independent of any controversy surrounding her 1973 victory over Bobby Riggs. Life magazine recognized her status by listing her among the 100 most important Americans of the 20th century. King's accomplishments include winning 12 major singles titles, founding the Women's Tennis Association, championing equal rights and LGBTQ causes, and establishing a longstanding philanthropic legacy. She is also a recipient of the Presidential Medal of Freedom. The U.S. Open is played annually at the Billie Jean King National Tennis Center, a major honor reflecting her profound impact on the sport and its inclusivity.
Martina Navratilova summed up King's significance by calling her a "crusader for all" who "carried the flag" for athletes. Navratilova asserted that Billie Jean validated the experience of being a jock and will always be the hero of this story, emphasizing the cultural reach of King’s impact and the enduring nature of her contributions well beyond the actual outcome of a single match.
Investigative journalist Don Van Natta Jr. addresses the theory that Bobby Riggs, possibly backed by the mafia, may have intentionally lost the match. Van Natta Jr. agrees that the immense cultural impact of the "Battle of the Sexes" cannot be erased or diminished, regardless of Riggs's intentions. He observes that the significance of Billie Jean King’s win—how it made men and women feel, and the cultural shift it provoked—remains unchanged even if the match were fixed.
Carter Roy echoes this view, highlighting that what Billie Jean King achieved was far more difficult than anything Riggs could have manipulated. She trained rigorously, performed at the highest level, endured enormous pressure, and emerged victorious with ease. No amount of speculation about her opponent's effort negates the fact that Billie Jean King became a feminist icon and an American hero that day. Van Natta Jr. notes that he has not proven the fix theory beyond doubt; rather, he has constructed a "pretty strong" circumstantial case supported by evidence, but he acknowledges room for the legitimacy of the match while offering an intriguing possible alternative history to one of sports’ most iconic moments.
Would Evidence Of a Fix Taint Billie Jean King's Legacy?
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