Beyond the Game: 15 Retired Athletes Who Mastered the Business World and Skyrocketed Their Wealth

Many professional athletes command astronomical salaries and endorsement deals during their prime, leading many to believe that their peak financial success occurs squarely within their playing careers. Indeed, the figures can be staggering, making it seem as though they are set for life the moment they decide to hang up their jerseys or cleats. However, a select group of visionary individuals has demonstrated that the end of an athletic career can, in fact, mark the true beginning of an even more lucrative financial journey, leveraging their built-in fame and competitive drive into unforeseen wealth.

These aren’t just stories of comfortable retirements; they are narratives of strategic pivots, astute investments, and entrepreneurial genius that have transformed athletic legends into business titans. The transition from the arena to the boardroom, from the court to venture capital, demands a different kind of discipline and foresight, but for those who master it, the financial rewards can far eclipse anything earned during their playing days. This article spotlights 15 such athletes who have masterfully orchestrated their post-sports careers to earn more annually than they did during their entire active professional careers.

Their journeys offer compelling insights into how a strong personal brand, coupled with smart decision-making and a relentless pursuit of new opportunities, can pave the way for extraordinary financial success long after the final whistle blows. We will delve into the specific strategies and ventures that enabled these individuals to not only maintain but significantly grow their fortunes, proving that for some, the greatest earnings come not from playing the game, but from mastering the business of life after the game.

1. **Tony Romo**Tony Romo’s NFL career spanned 13 years entirely with the Dallas Cowboys, where he was signed as an undrafted free agent in 2003. A four-time Pro Bowler, he holds the franchise record for passing yards with 34,183. He earned an estimated $127 million during his playing days, becoming one of the highest-paid undrafted players.

Upon retirement, Romo made a swift, lucrative pivot to sports broadcasting, joining CBS as an analyst. His insightful commentary and play anticipation quickly captivated audiences. Initially earning around $12 million annually, this move immediately boosted his post-playing income.

In 2020, Romo’s broadcasting career soared with a multi-year deal with CBS, reportedly worth $180 million, to become their lead color analyst alongside Jim Nantz. This contract alone represents a monumental increase over his NFL earnings.

Further enhancing his portfolio, Romo secured strategic endorsement deals. Partnerships with DirectTV, Under Armour, and Pizza Hut leverage his recognition, adding significant revenue streams to his post-retirement fortune.

2. **Serena Williams**Serena Williams’s tennis career, spanning nearly three decades, stands as a monument to athletic excellence. She secured 23 Grand Slam titles and four Olympic gold medals, earning approximately $95 million in prize money—a record for any female tennis player.

After her 2022 retirement, Williams’s wealth dramatically soared, showcasing a powerful transition to astute business acumen. Her venture capital firm, Serena Ventures, has become a significant investment entity, deploying capital into over 60 startups including Tonal and Impossible Foods.

Williams also successfully launched her own clothing line, “S by Serena,” leveraging her distinctive style and global brand appeal into the fashion industry. This direct engagement in retail further diversified her business interests.

Additionally, she strategically entered sports ownership as an investor and part-owner of Angel City FC, an NWSL team in Los Angeles. This involvement aligns with her passion for women’s sports while representing a smart investment, contributing to her estimated net worth of $340 million.

“Super Bowl-2-2” by StephenLukeEdD is licensed under CC BY 2.0

3. **Michael Strahan**Michael Strahan, a defensive end for the New York Giants, was a dominant force for 15 seasons, culminating in a Super Bowl XLII victory. During his legendary NFL career, he earned over $75 million, establishing a solid financial base.

Following retirement, Strahan executed a masterful transition into broadcasting and entertainment, significantly amplifying his financial success. He contributed to Fox’s NFL coverage from 2008, then broadened into high-profile talk show roles.

His charisma made him a natural fit for television, co-hosting “Live! With Kelly and Michael” and later joining “Good Morning America.” Reports indicated he earned upwards of $20 million annually from his television work at one point, far exceeding his NFL salary. NewsNation reported he is set to leave “Good Morning America” in summer 2025.

Strahan also engaged in lucrative endorsement deals with brands like Snickers and Pizza Hut, diversifying his income. Rumors even suggest he might purchase a stake in his former team, the New York Giants, expanding his influence and wealth, currently estimated at $65 million.

“Greg Norman Photo by Ted Van Pelt” by Ted Van Pelt is licensed under CC BY 2.0

4. **Greg Norman**Greg Norman, “The Great White Shark,” dominated golf in the 1980s and 1990s, spending 331 weeks as World No. 1. He achieved 88 professional wins, including two Open Championships, and earned over $17 million in career prize money.

Post-retirement, Norman transformed into an extremely influential entrepreneur, building a vast and diverse business empire through the Greg Norman Company. His vision extended into multiple industries, leveraging his global brand and expertise.

The Greg Norman Company’s portfolio includes successful golf course design, with over 100 courses worldwide. His ventures also encompass the Greg Norman Collection apparel line, Greg Norman Estates wineries, real estate, and hospitality, such as the Greg Norman Grille.

A notable business success was his 1991 investment in Cobra Golf, where a $1.9 million outlay yielded a $40 million profit. He also served as CEO of LIV Golf from 2021 to 2025. His estimated net worth now stands at $400 million, underscoring his extraordinary post-retirement success.

5. **Shaquille O’Neal**Shaquille O’Neal, a basketball legend, earned over $290 million during his illustrious NBA career. His powerful dominance and charismatic personality made him a global superstar. However, his shrewd, diverse off-court business plays post-retirement significantly swelled his portfolio.

Shaq’s entrepreneurial ventures include major stakes in numerous restaurant chains. His portfolio features Papa John’s, Krispy Kreme, and Big Chicken franchises; he previously owned upwards of 155 Five Guys locations.

He also displayed remarkable foresight with early technology investments. His initial stakes in Google, home security company Ring (sold to Amazon for $1 billion), and ridesharing platform Lyft paid significant dividends, highlighting his understanding of market trends.

His engaging personality and basketball knowledge also secured a lucrative media career. As a popular co-host of “Inside the NBA,” O’Neal recently signed a new contract earning him $15 million annually. His estimated net worth of $500 million exemplifies his post-retirement financial genius.

6. **Magic Johnson**Earvin “Magic” Johnson, alongside Kareem Abdul Jabbar, led the ‘Showtime’ Lakers to five NBA championships, earning significant on-court income. Yet, his post-playing career built an extraordinary financial empire, demonstrating unparalleled business acumen.

Magic Johnson Enterprises now encompasses a diverse portfolio of investments. A notable early move was investing in Starbucks franchises, particularly in underserved neighborhoods, a venture that reportedly netted him over $70 million upon sale.

His business interests extend into real estate through the Canyon Johnson Urban Fund, focused on urban communities. He also strategically invested in movie theaters, diversifying his impressive portfolio.

A celebrated move was his $50 million investment in the Los Angeles Dodgers in 2012, an asset that has greatly appreciated. He also holds stakes in the LA Sparks (WNBA) and LA Football Club (MLS). Coupled with his success as a motivational speaker and television personality, Johnson’s empire results in an estimated net worth of $1.5 billion.

7. **David Beckham**David Beckham, a global soccer superstar for clubs like Manchester United, Real Madrid, and the LA Galaxy, earned substantial salaries and bonuses. His 2007 LA Galaxy contract was particularly lucrative, a five-year deal worth approximately $250 million, including salary, endorsements, and revenue sharing, making him one of the highest-paid MLS players.

Post-retirement, Beckham forged an extraordinary business empire by leveraging his unparalleled global brand. He transformed his celebrity into a powerful asset, securing long-term partnerships, including a lifetime Adidas deal reportedly worth $160 million.

Beckham’s endorsement portfolio includes Pepsi, Gillette, Armani, and Maserati. Beyond endorsements, he co-founded DB Ventures and sold a 55% stake for a remarkable $269 million.

Exercising an MLS team option from his LA Galaxy contract for $25 million, Beckham purchased and established Inter Miami CF. The team’s valuation skyrocketed after signing Lionel Messi, making Beckham’s initial investment now worth around $110 million. His estimated net worth of $450 million demonstrates his financially rewarding post-playing career.

Building on the theme of post-retirement financial success, this section will highlight eight more extraordinary athletes who defied conventional expectations by accumulating greater wealth after stepping away from their respective sports. We will scrutinize the diverse paths taken by Roger Staubach, Jim Brown, Tony Hawk, Arnold Palmer, John Elway, Peyton Manning, George Foreman, and Michael Jordan, detailing their key investments, brand-building strategies, and innovative business moves that cemented their status as financial titans beyond the playing field.

8. **Roger Staubach**Roger Staubach, famously known as “Captain America,” was an undisputed leader on the field for the Dallas Cowboys from 1969 to 1979. During his illustrious 11-season NFL career, he secured two Super Bowl championships (VI, XII) and was named Super Bowl MVP for Super Bowl VI. Despite his phenomenal success and impact, his total playing salary was a modest $1.5 million by today’s standards.

However, Staubach proved to be as strategic in business as he was on the gridiron. Even while still actively playing, he demonstrated incredible foresight by co-founding The Staubach Company, a commercial real estate firm. This early venture laid the groundwork for his immense post-retirement wealth, highlighting his proactive approach to life after football.

The Staubach Company quickly grew into a major player in the commercial real estate market, brokering significant deals for corporate giants such as AT&T and McDonald’s. His reputation for integrity and strategic thinking earned him widespread respect in the business world, translating his athletic discipline into entrepreneurial triumph.

In 2008, Staubach made a monumental financial move, selling his firm for a staggering $613 million. This sale represented an astronomical profit from his initial $100,000 investment, showcasing one of the most successful transitions from sports star to business mogul. Today, his estimated net worth stands at an impressive $600 million, a testament to his unparalleled business acumen.

9. **Jim Brown**Jim Brown redefined the running back position during his nine dominant seasons with the Cleveland Browns from 1957 to 1965. Despite an unparalleled NFL career, he shocked the sports world by retiring at the peak of his powers at age 29, opting to pursue an acting career. This bold pivot proved to be a lucrative decision, diversifying his income streams beyond the gridiron.

Brown went on to star in over 30 films, including notable titles like “The Dirty Dozen” and “Any Given Sunday,” earning millions through his cinematic endeavors. His powerful on-screen presence and undeniable charisma allowed him to carve out a successful second career in Hollywood, proving his versatility and appeal extended far beyond football.

Beyond acting, Brown continued to expand his financial portfolio through various media appearances, insightful sports commentary, and astute investments. He understood the value of his personal brand and leveraged it effectively to maintain a public profile and generate additional revenue streams throughout his life.

Furthermore, Brown was a dedicated advocate for social and economic empowerment, notably co-founding the Black Economic Union to support African-American businesses. His investments in real estate and entertainment ventures further solidified his financial foundation, contributing to his estimated net worth of $40 million at the time of his passing in 2023.

10. **Tony Hawk**Tony Hawk wasn’t just a skateboarder; he was an icon who captivated a generation of youth in the 1980s and 1990s. With 12 world championships and 16 X-Games medals under his belt, he built a significant fortune through prize money and lucrative sponsorships from prominent brands like Birdhouse and Quiksilver. At his competitive peak in the ’90s, he was reportedly earning an impressive $10 million annually.

However, it was a single video game series that catapulted his fame and fortune to stratospheric levels: “Tony Hawk’s Pro Skater.” Launched in 1999, the game became an instant smash hit, and the entire series has since generated over $1.4 billion in revenue. Hawk’s shrewd royalty deals from this franchise have consistently delivered substantial earnings, showcasing the power of brand licensing.

The enduring popularity of the “Tony Hawk’s Pro Skater” series is remarkable, with new iterations, including a remake of the original two games (“Tony Hawk’s Pro Skater 3+4”), set to release in 2025. This continuous engagement with his gaming legacy ensures a steady flow of income, demonstrating the lasting impact of a well-cultivated brand in the digital age.

Beyond gaming, Hawk’s entrepreneurial spirit led him to found Birdhouse Skateboards and Hawk Clothing, further solidifying his brand’s presence in the extreme sports lifestyle market. Coupled with his extensive media presence and ongoing endorsements, these ventures have collectively swelled his portfolio to an estimated net worth of $140 million, proving his vision extends far beyond the half-pipe.

11. **Arnold Palmer**Arnold Palmer, affectionately known as “The King,” transcended the sport of golf to become one of the most iconic figures in sports history. His incredible talent on the course saw him win seven major championships, but it was his pioneering approach to off-course business that truly established his legendary financial empire.

Palmer was a trailblazer in athlete endorsements, forging highly successful partnerships with major brands such as Pennzoil, Cadillac, and Rolex. He understood the immense value of his charisma and appeal, leveraging it to create a template for how athletes could build lucrative careers beyond their playing days. His name became synonymous with excellence and authenticity.

His entrepreneurial spirit further manifested in the establishment of Arnold Palmer Enterprises, a comprehensive company managing his diverse business ventures. A cornerstone of this empire was the highly successful Arnold Palmer Design Company, responsible for designing hundreds of golf courses worldwide, leaving an indelible mark on the global golf landscape.

Perhaps his most recognizable and enduring legacy outside of golf clubs is the refreshing beverage bearing his name: the “Arnold Palmer.” In 2001, the AriZona Beverage Company secured a licensing agreement to produce this iconic iced tea mixed with lemonade, a venture that generates approximately $200 million in annual revenue. At the time of his passing in 2016, his estimated net worth was a staggering $875 million, solidifying his status as a true business titan.

12. **John Elway**John Elway stands as a legendary figure in the annals of NFL history, having spent an astonishing 16 years as the quarterback for the Denver Broncos. During his storied career, he earned approximately $47 million in salary and bonuses, securing his place as a highly compensated athlete of his era. However, his financial trajectory significantly accelerated after he hung up his cleats.

Upon retirement, Elway seamlessly transitioned his competitive drive into the business world, establishing a highly successful chain of car dealerships under the John Elway Dealership Group. This venture quickly became a major player in the Colorado automotive market, demonstrating his keen eye for business and effective leadership outside of football.

His entrepreneurial spirit wasn’t limited to automobiles. Elway diversified his portfolio with ventures in upscale dining, launching Elway’s steakhouses, and strategic real estate investments. He also ventured into the beverage industry with 7Cellars, a wine brand that successfully gained nationwide recognition, appealing to a broad consumer base.

Further adding to his post-playing career earnings, Elway served as the General Manager for the Denver Broncos from 2011 to 2021, a role that reportedly earned him $3 million annually. This combination of shrewd business investments and continued involvement in the NFL contributed to his impressive estimated net worth of $145 million.

13. **Peyton Manning**Widely regarded as one of the greatest quarterbacks of all time, Peyton Manning’s 18-season NFL career was nothing short of legendary, primarily with the Indianapolis Colts and later with the Denver Broncos, where he signed a massive 5-year contract worth $96 million. While his on-field earnings were substantial, his post-retirement endeavors have strategically grown his wealth to even greater heights.

Since retiring, Manning has masterfully cultivated multiple revenue streams, most notably through an extensive portfolio of endorsement deals. His long-running partnership with Nationwide Insurance, along with other major brands, continues to generate significant income, leveraging his widely recognized and respected personal brand.

Manning has also seamlessly transitioned into a prominent media career, notably as a football analyst. His substantial salary as an analyst on Monday Night Football showcases his continued relevance and appeal to a vast audience, offering insightful commentary and engaging analysis.

In a truly innovative move, Manning, alongside his brother Eli, owns the production company responsible for the highly popular “Manningcast,” a Monday Night Football alternative broadcast. This venture, secured through a lucrative 9-year deal with ESPN (though its value remains undisclosed), exemplifies his entrepreneurial vision. Complementing this, he also owns several Papa John’s franchises across Colorado and has invested in various other restaurant chains and businesses, contributing to his estimated net worth of $250 million.

14. **George Foreman**George Foreman, a two-time heavyweight boxing champion and Olympic gold medalist, earned approximately $40 million in prize money during his illustrious career in the ring. However, his most significant financial knockout came from an entirely unexpected source, transforming him from a boxing legend into a household name in consumer goods.

Foreman had no inkling that his endorsement of a simple kitchen appliance, the ‘George Foreman Grill,’ would become a global phenomenon. Initially viewing it as a way to provide free grills to his family members, he soon discovered they were sitting on an unprecedented goldmine. The grill, launched in 1996, went on to sell more than 100 million units worldwide.

The success of the ‘lean, mean, fat-reducing machine’ was monumental. Although the exact figures of Foreman’s earnings from the grills are not fully disclosed, he famously stated he was making up to $8 million a month at the peak of its popularity. He eventually sold his naming rights to the grill company for a massive lump sum, reportedly exceeding $200 million, a figure that dwarfed his entire boxing career earnings.

This incredible venture solidified Foreman’s status as one of the most successful celebrity endorsers of all time, demonstrating how a powerful personal brand, coupled with the right product, can generate extraordinary wealth far beyond the confines of sports. His estimated net worth now stands at $300 million, largely thanks to his visionary business move.

“Michael Jordan” by alexwaltasss is licensed under CC CC0 1.0

15. **Michael Jordan**Michael Jordan, unequivocally recognized as “The GOAT” both on and off the court, earned around $90 million during his entire legendary NBA career. While this sum is substantial, it is absolutely dwarfed by the staggering fortune he has amassed in his post-retirement endeavors, cementing his status as the wealthiest athlete ever.

The cornerstone of Jordan’s post-playing wealth is the iconic Air Jordan brand at Nike. His partnership with the sportswear giant, which began in 1984, continues to generate billions in revenue annually for Nike, while providing Jordan with massive royalties. This collaboration transformed athletic endorsements and created a global cultural phenomenon, showcasing the enduring power of his personal brand.

In a testament to his business acumen and understanding of asset valuation, Jordan made headlines in 2023 when he sold his majority stake in the Charlotte Hornets NBA franchise for an astounding $3 billion. This monumental transaction solidified his position as a shrewd investor, proving his Midas touch extends beyond the basketball court.

Beyond Nike and the Hornets, Jordan’s diversified empire includes lucrative endorsement deals with global brands like Hanes, Gatorade, and Upper Deck, ensuring a continuous flow of cash. He has also ventured into the hospitality sector with his own steakhouses and even owns a NASCAR team, demonstrating a broad range of entrepreneurial interests.

Forbes officially ranks Michael Jordan as the wealthiest athlete ever, with an estimated net worth of $3.5 billion. His journey is a masterclass in leveraging athletic greatness into an unparalleled business empire, proving that for some, the greatest game is played in the boardroom long after the final buzzer sounds.

These 15 extraordinary athletes have undeniably rewritten the playbook for post-retirement success. Their stories are a compelling testament to the fact that for a select few, hanging up their jerseys or cleats isn’t an ending, but a powerful launchpad into a new arena where strategic vision, shrewd investments, and an unyielding entrepreneurial spirit can lead to financial triumphs that far exceed their playing days. Their journeys offer invaluable insights into the enduring power of a well-cultivated personal brand and the remarkable potential for wealth creation when competitive drive is channeled into business innovation. It’s a powerful reminder that the lessons learned on the field can translate into an even greater legacy off it, shaping industries and inspiring generations.