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© History Oasis
The insurance industry rewards growth and profit above almost everything else. CEOs who push boundaries get rich. Those who cross lines pay fines but rarely face prison. Here is a list of famous insurance leaders who shaped the business.
CEO of USAA (1969-1993)
Robert Davis led USAA, a small military auto insurer, and turned it into a financial giant. Davis, an Air Force major general, ran the company with military precision and pioneered mobile banking via mail and phone systems. Assets grew from $200 million to over $23 billion under his watch. Notoriously, he once rejected an ad campaign because a soldier’s uniform had the wrong number of buttons.
CEO of Prudential (1994-2007)
The man who took Prudential public in 2001 and became the largest IPO in U.S. history at the time. Arthur Ryan inherited a $2 billion sales fraud settlement where agents had convinced customers to cash out old policies and buy new ones. The scheme generated commissions while destroying customer value. Ryan spent years rebuilding trust while the company remained under regulatory supervision until 2012.
CEO of AIG (2009-2014)
Robert Benmosche took over AIG in 2009 after its government bailout. He arrived from his vineyard in Croatia while dying of cancer and spent his first weeks managing via conference call, infuriating Washington politicians. Benmosche sold off AIG divisions to repay taxpayers, turning a potential $30 billion loss into a $22 billion profit for the government. When politicians demanded executives return their bonuses, he compared the outcry to Southern lynch mobs. He died in 2015 after saving the company but never softening his abrasive style.
CEO of State Farm (1985-2015)
Edward B. Rust Jr. ran State Farm for three decades. He maintained its position as America’s largest auto insurer. He kept the company private and avoided the spotlight. During Rust’s tenure, State Farm paid $1.2 billion to settle claims it used aftermarket parts instead of original equipment in auto repairs. The company also faced allegations of fraudulent claim practices after Hurricane Katrina, with internal emails suggesting State Farm pressured engineers to blame water damage instead of wind damage to deny claims.
CEO of MetLife (1989-1993)
The leader who introduced the Snoopy mascot to MetLife. John Creedon pushed MetLife to diversify beyond life insurance. He spent $1.6 billion acquiring businesses, including Century 21 Real Estate. Wall Street loved the strategy at first. But then the real estate market crashed, and MetLife lost hundreds of millions. Creedon stepped down earlier than planned as losses mounted.
CEO of Cigna (2009-2021)
David Cordani became Cigna’s solo CEO in 2009 during the Affordable Care Act debates. He orchestrated the $67 billion merger with Express Scripts in 2018, creating a pharmacy-insurance behemoth. Cordani first survived a failed $54 billion merger attempt with Anthem between 2015 and 2017. When Anthem tried to back out, Cigna sued for $15 billion in damages. The companies settled for $2 billion.
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CEO of UnitedHealth (1991-2006)
William McGuire built UnitedHealth into the largest health insurer in America. He would become a billionaire in the process. His compensation reached $124.8 million in 2005 alone. Investigators discovered McGuire had backdated stock options worth $1.6 billion over 15 years. He resigned in 2006 and paid a $468 million settlement, the largest executive penalty in U.S. history. Prosecutors never filed criminal charges. McGuire kept roughly $800 million.
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