By Haddon Libby
At the absolute peak of global compensation sit with two very different groups: elite athletes and corporate chief executives. Both can clear the nine-figure mark, but the money comes from very different places.
In sports, the biggest paydays come from guaranteed contracts, global audiences and endorsement empires. Soccer player Cristiano Ronaldo remains in a class of his own at about $275 million per year, driven largely by his Saudi-backed salary with Al-Nassr and a global sponsorship machine that follow him wherever he plays.
Golden State Warrior, Stephen Curry, at roughly $156 million, shows how modern athlete income extends well beyond the playing field. His Golden State Warriors salary is capped by NBA rules, but his lifetime Under Armour partnership and equity incentives helped push his off-court earnings above his on-court pay.
The rest of the sports list shows the same pattern in different forms. Tyson Fury earned about $146 million from heavyweight prize fights staged in Saudi Arabia. Dallas Cowboy Quarterback Dak Prescott reached roughly $137 million because of a heavily front-loaded contract extension. Soccer player Lionel Messi earned about $135 million through a creative Inter Miami (MLS) deal that blends salary, Apple TV revenue-sharing and Adidas merchandise economics.
Athletes monetize scarcity, audience attention and guaranteed contracts. CEOs, by contrast, are usually paid through equity packages whose reported value depends on stock performance, vesting conditions and investor expectations. Both groups can reach astonishing headline numbers, but the machinery behind those numbers is very different.
As an example, Elon Musk’s reported Tesla package of $132 billion sits in its own category because it is tied almost entirely to long-term equity incentives rather than salary. The headline number is less a paycheck than a claim on future corporate value, tied to performance milestones and market capitalization targets. With the IPO of SpaceX, Musk is estimated to have a net worth in the $1 trillion range.
The other executive packages are smaller than Musk’s but still staggering. Dylan Field of tech company Figma had a reported $864 million package tied to his equity as the founder of the company and stock-based incentives. This occurred despite the cloud-based design company being expected to lose about $1.25 billion this year. Shankh Mitra of Welltower received a reported $821 million conditional stock grant tied to long-term shareholder results; Welltower, unlike several others on the list, earned about $973 million last year.
Kasra Nejatian of Opendoor and Robert Scaringe of Rivian show the more speculative side of executive pay. Nejatian’s reported $741 million package is tied to a turnaround at a volatile real estate technology platform that lost about $392 million last year. Scaringe’s reported $403 million Rivian package depends on production and market-value goals at an electric vehicle maker that lost about $4.75 billion in its last fiscal year.
The earnings of Hollywood stars now look almost modest by comparison. Adam Sandler, the top-paid actor, is expected to make a little less than $50 million this year. That is an extraordinary income, but streaming economics and limited equity participation tend to cap actor pay below superstar athletes and equity-heavy CEOs.
The gap with ordinary pay is even more striking. The median full-time U.S. worker earns about $62,600 a year. The median chief executive across the broader economy earns about $214,000, while the typical S&P 500 CEO earns roughly $17.7 million. The median professional athlete earns about $65,000, proving that the superstar economy is not the same as the profession itself.
These extreme paydays are not just salaries; they are claims on attention, ownership and future value. Whether through guaranteed sports contracts, celebrity brands or executive equity awards, today’s richest earners are paid less for hours worked than for the economic ecosystems built around them.
Haddon Libby is the Founder and Chief Investment Officer of locally-based Fiduciary RIA investment advisory firm, Winslow Drake. For more information on our services or to request a free investment portfolio review, please email Haddon at hlibby@winslowdrake.com or visit www.WinslowDrake.com.
