.png)
.webp)
© History Oasis / Created via Midjourney
1922-1928
In the summer of 1922, Major William Howard Garrison assembled 25 Army officers at San Antonio’s Gunter Hotel. Their mission was to create affordable auto insurance for military officers deemed “high-risk” by other insurers.
Garrison established USAA’s foundational principle of mutual self-insurance, expanding eligibility first to Navy and Marine Corps officers in 1923. The next year, he renamed the org from “United States Army Automobile Association” to “United Services Automobile Association.”
When he stepped down, Garrison had built a membership of 7,500 service members with $300,000 in assets.
1928-1941
The Great Depression threatened America’s financial system. USAA faced internal strife.
Major General Ernest Hinds arrived to lead with a steady hand. A decorated artillery officer, he implemented conservative investment strategies focused on government securities. This prudence saved USAA when countless insurers collapsed.
In 1934, Hinds expanded membership to Foreign Service officers and State Department officials. His innovative Safe Driver Reward Plan (1938) pioneered incentive-based insurance decades before competitors.
Assets multiplied fivefold during his tenure, reaching $2.2 million when Hinds died in 1941.
1941-1948
As America entered World War II, Herbert White confronted operational challenges: paper rationing restricted communications, qualified workers enlisted for combat, and policyholders scattered across global theaters of war.
He modernized operations by implementing IBM punch-card machines in 1946—USAA’s first automation system. This dramatically improved efficiency and set the company up for expansion after the war.
1948-1952
William Franklin Jones led the USAA when the National Security Act of 1947 restructured America’s defense establishment, creating the independent Air Force.
Jones recognized opportunity in change. He rapidly extended membership eligibility to Air Force officers in 1948.
His brief leadership coincided with the Korean War, requiring adaptive policies for members deployed to another overseas conflict.
1953-1969
Sixteen years of steady growth defined Charles Cheever Sr.’s impact.
Membership expanded fivefold. Assets surged from $16 million to $200 million. This was during Cold War tensions, civil rights movements, the Vietnam War, and the space race.
Through it all, Cheever maintained organizational stability.
His most enduring contribution? Founding Broadway Bank in San Antonio, which strengthened USAA’s Texas roots while expanding financial offerings to members. Setting the stage for USAA’s expansion outside of insurance.
1969-1993
Brigadier General Robert Frederick McDermott, affectionately known as “McD,” led the company for over 24 years.
Before he arrived, USAA was a niche insurer with limited services. But after he arrived, it became a diversified financial powerhouse with 15,000 employees and $33 billion in assets.
1993-2000
“Access for all who serve.” This vision was created by General Robert Tyson Herres.
Previously Vice Chairman of the Joint Chiefs of Staff, Herres possessed a strategic mind. He recognized restricting membership to officers excluded millions of potential members who shared identical values and needs.
In 1996, Herres opened membership to enlisted personnel—instantly doubling USAA’s market potential. This democratization of access honored all services rather than rank alone.
He also moved the org into the digital age. USAA.com launched in 1999, just before the millennium. Electronic banking expanded.
2000-2007
“Grow or die.” Robert Gordon Davis embraced this philosophy with determination—and controversy.
The former Army officer accelerated USAA’s evolution into a full-service financial institution. Assets surpassed $100 billion. Net worth doubled. Online services expanded dramatically.
Davis introduced Deposit@Home in 2006, allowing members to scan checks for deposit—a revolutionary convenience. But his confrontational leadership style generated friction. He implemented USAA’s first-ever layoffs, shocking the company’s culture.
His sudden 2007 departure raised eyebrows. His successor later admitted: “I thought I was just going to be a temporary CEO, and then the board said, ‘Guess what? The permanent CEO is you.’”
2007-2015
They called him “the people’s general,” and Major General Josue “Joe” Robles Jr. lived up to the nickname.
In 2009, Robles opened membership to all honorably discharged veterans, potentially creating millions of new members. Simultaneously, he launched USAA’s app with mobile check deposit capability.
The results? Extraordinary growth: Membership increased 53%, revenue jumped 45% — and members received $7.3 billion through dividends, distributions, and rebates
Robles secured the NFL partnership as “Official Military Appreciation Sponsor” in 2011, raising USAA’s national profile.
2015-2020
From fighter pilot to financial leader—Stuart Parker was the perfect fit for USAA’s unique culture.
Parker joined USAA in 1998 as a financial planner after his Air Force career. Rising through the ranks, he ultimately secured USAA’s position on the Fortune 100 list in 2018. His employee-focused initiatives included:
In 2019, he sold USAA’s investment management arm to Charles Schwab for $1.8 billion. This divestment allowed for greater focus.
His departure featured a controversial $6.5 million severance package.
2020-2025
When crisis struck, Wayne Peacock—USAA’s first non-veteran CEO—faced a baptism by fire.
COVID-19 hit one month after his appointment. Peacock orchestrated the rapid transition of 36,000 employees to remote work in just nine days. Despite the pandemic’s challenges, he implemented progressive workplace policies by raising the minimum wage and expanding benefits.
Difficulties mounted. In 2022, USAA received a $140 million penalty for Bank Secrecy Act violations. That same year, the company also had its first annual loss in a century ($1.3 billion). Yet by 2023, Peacock had guided USAA back to profitability.
2025-present
With 40 years in financial services, including leadership at Everest Group, Chubb, The Hartford, and Progressive, Andrade brings diverse expertise. His four years on USAA’s board provided invaluable institutional knowledge.
Though not a veteran, Andrade’s public service earned him the Secretary of Defense Medal for Meritorious Civilian Service for counter-narcotics work.
Andrade inherits a profitable organization with $211.6 billion in assets serving 13.5 million members.
.webp)
.webp)
.webp)