Celebrity Sports Engagements – Where Romance Meets Fame and Fortune: Part 2

Author: Sam Davies

Last week, in the first part of this sequel, we explored iconic sport celebrity engagements like Travis Kelce and Taylor Swift, Cristiano Ronaldo and Georgina Rodríguez, and David and Victoria Beckham and how they became global talking points. But those weren’t the only sporting icons whose love stories captivated the world. In this second part, we look at three more unforgettable unions – Serena Williams and Alexis Ohanian, Michael Jordan and Yvette Prieto, and Tom Brady and Gisele Bündchen. These power couples’ stories show how love at the highest level of sport becomes a cultural milestone, complete with luxury rings, media spectacle, and even a touch of betting buzz.

4. Serena Williams & Alexis Ohanian: A Grand Slam Engagement

When tennis legend Serena Williams and Reddit co-founder Alexis Ohanian announced their engagement in December 2016, it was more than just another celebrity love story; it was a cultural moment that blended sport, technology and business into a single headline. Their relationship illustrates how modern sports engagements can symbolize not just romance but the merging of industries and identities.

Timeline of the Relationship

Williams and Ohanian first met by chance in Rome in 2015, when they were staying at the same hotel while Serena was competing in the Italian Open. After a year of dating, Ohanian proposed in December 2016 in the very city where they first met, setting the scene at the Cavalieri Hotel with a table for two and a rose petal trail spelling out the words “Marry Me”. The engagement was revealed in a poem that Serena posted – fittingly – on Reddit. They married in November 2017 in New Orleans in a star-studded ceremony attended by Beyoncé, Kim Kardashian and Anna Wintour.

• Serena Williams Engagement Ring: $2,000,000 - $3,000,000

Serena’s engagement ring is as striking as her career achievements. The massive emerald-cut diamond, estimated at 12-14 carats, is valued between $2 million and $3 million. Its sleek and modern design reflects Serena’s bold sense of style while standing as one of the most talked-about rings to be placed on a celebrity’s fingers in the modern era.

• Ring Cost vs. Earnings: A Drop in a Bucket

By 2016, Serena Williams was already one of the highest-paid athletes in the world, with career prize money exceeding $80 million and lucrative endorsements adding tens of millions more. For Ohanian, whose net worth had surpassed $9 billion thanks to Reddit’s growth and investments in tech, the multimillion-dollar ring was financially feasible. If taken against Serena’s yearly endorsements alone (around $20 million at the time), the $3 million ring would represent about 15% of one year’s endorsement income: a substantial but fitting tribute. Of course, if you compared it to Ohanian’s net worth, it would barely scratch the surface.

• Cultural & Media Impact

Unlike some sports-star engagements that lean heavily on spectacle, Williams and Ohanian’s story resonated because of its symbolism. The union of one of the most dominant athletes of all time and a tech entrepreneur underscored broader cultural narratives: the crossing of industries, the rise of power couples, and the blending of tradition with modern storytelling.

Their wedding was another cultural milestone, with Vogue publishing exclusive photos and fashion press hailing Serena’s multiple designer gowns. Yet what stood out most was how Serena, a global sports icon, chose to share her engagement on Reddit, a platform co-founded by her fiancé. For fans, the engagement showcased the modern face of sports celebrity: one where relationships are celebrated as global news stories, complete with multimillion-dollar jewelry, viral social media announcements, and coverage that extends far beyond the back pages.

5. Michael Jordan & Yvette Prieto: The GOAT’s Lavish Second Chapter

Michael Jordan’s life off the court has often mirrored the grandeur of his playing career. After dominating the NBA, building a billion-dollar brand, and becoming an icon well beyond basketball, his engagement to Cuban-American model Yvette Prieto made headlines as a testament to his enduring status as the sport’s ultimate superstar. Their story demonstrates how even retired athletes continue to shape cultural narratives when love, luxury and legacy collide.

Timeline of the Relationship

Jordan met Prieto in 2008 at a Miami nightclub, years after his divorce from his first wife, Juanita Vanoy. The two quickly became inseparable, with Prieto regularly accompanying Jordan to public events. By Christmas 2011, after three years of dating, Jordan proposed. The couple wed in April 2013 in Palm Beach, Florida, in a ceremony estimated to have cost upwards of $10 million. Guests included celebrities and athletes from across the world, while Usher and Robin Thicke performed at the reception.

• The Ring: $1,000,000 - $3,000,000

Jordan spared no expense on Prieto’s engagement ring. The diamond is widely reported to be 15 carats, set on a platinum band, with a valuation estimated between $1 million and $3 million. Its clean design and sheer size make it one of the most extravagant rings among sports star engagements, befitting Jordan’s reputation for doing everything on the grandest scale.

• Ring Cost vs. Earnings

By the time of his engagement, Jordan was no longer earning NBA salaries but had become a billionaire through endorsements and ownership of the Charlotte Hornets. In 2011, Forbes estimated his annual income at around $80 million, largely from his iconic Nike Air Jordan brand. Put in perspective, a $2 million ring would represent 2.5% of a single year’s earnings.

• Cultural & Media Impact

The media framed Jordan and Prieto’s engagement as the ultimate luxury story: a global icon finding love again, capped by a multimillion-dollar ring and one of the most expensive celebrity weddings in history. But beyond the extravagance, the engagement reinforced Jordan’s enduring relevance. Even a decade after his final retirement, his personal milestones commanded international headlines.

6. Tom Brady & Gisele Bündchen: Power Couple Perfection?

Few athlete-celebrity pairings embodied global stardom quite like Tom Brady and Gisele Bündchen. Their 2009 engagement and subsequent marriage fused the worlds of sport and fashion into one of the most iconic power couples of the 21st century.

Timeline of the Relationship

Brady, then quarterback of the New England Patriots, began dating Bündchen, the Brazilian supermodel and former face of Victoria’s Secret, in 2006. After three years together, Brady proposed in January 2009, reportedly filling a private jet with white roses before popping the question. The pair married weeks later in a small ceremony at a Catholic church in Santa Monica, followed by a larger celebration in Costa Rica.

• Cultural & Media Impact

Bündchen’s engagement ring reflected her understated elegance: a solitaire diamond estimated at around 4 carats, valued between $145,000 and $300,000. While modest compared to some celebrity rings, its refined simplicity matched Bündchen’s personal style and the couple’s relatively private approach to their union.

• Ring Cost vs. Earnings

By 2009, Brady’s annual salary with the Patriots was about $14 million. Even at the highest estimate, the ring cost represented just over 2% of a year’s salary. Bündchen herself was one of the world’s highest-paid models, earning more than $25 million that same year. The financial symbolism was clear: they were a couple whose wealth was abundant and balanced, each bringing immense success in their own right.

• Cultural & Media Impact

Brady and Bündchen’s marriage was hailed as the ultimate merger of sport and fashion, with tabloids hailing a perfect couple. Even after their divorce in 2022, their legacy as a power couple remains almost unmatched.

The Business of Betting on Love

When superstar athletes get engaged, the headlines rarely stop at romance. Modern sportsbooks have discovered that the public’s fascination with celebrity relationships is fertile ground for novelty markets.

Operators like BetRivers, Caesars and Borgata routinely post specials on high-profile couples. After rumors of Travis Kelce’s proposal to Taylor Swift swirled, odds appeared on everything from wedding dates to first-dance songs. Royal weddings, Kardashian pregnancies and Hollywood breakups have received similar treatment. These markets aren’t huge revenue drivers, but they generate buzz, free publicity and endless social chatter.

If there’s a lesson in this fusion of romance and odds-making, it’s that in today’s celebrity culture, nothing stays purely private. Whether in stadiums or tabloids, the line between passion and prop bet keeps narrowing. And for operators and audiences, that’s half the fun.