How a $266 Million Win Turned Jacki and Gil Cisneros Into Life-Changers

Winning $266 million in Mega Millions back in 2010 didn’t just change Jacki and Gil Cisneros’ bank account — it reshaped their purpose. Before they ever bought a mansion or replaced Gil’s beat-up pickup, the couple jumped straight into giving back. They launched the Gilbert & Jacki Cisneros Foundation, which later helped build the Cisneros Hispanic Leadership Institute at George Washington University.

But rewind a little. One spring night, on the way to a “big splurge” dinner at Outback, the couple played a simple game: What if we won the lottery? Gil said he’d want to help kids get to college so they didn’t have to struggle the way he did. Two weeks later, Jacki got the shocking news — someone had bought the winning ticket at the same spot where Gil grabbed dinner. The number check confirmed it: they were the winners.

A Life Rewritten

Instead of falling into the typical “lottery curse,” the Cisneroses went the opposite direction. They credit their philanthropy with keeping them grounded.

They’ve since:

• Helped hundreds of students, especially Latino students, access college

• Funded major scholarship programs, including one at USC

• Supported leadership initiatives that continue to launch first-gen students into top-tier schools

Enrique Flores, for example, went from their summer program to Stanford — earning both a bachelor’s and master’s. Another student, Elisa Velasco, built her own no-cost education program in Oklahoma after being inspired by the foundation’s work.

Their Own Family Dream

Money also unlocked something intensely personal: parenthood. The couple once assumed children weren’t in their future—opposite schedules, fertility issues, debt. But winning changed that. Jacki went through IVF and welcomed twins in 2014.

Staying Grounded

Even with wealth, they learned some hard truths — like how a $165 million lump sum drops to around $90 million after taxes. They surrounded themselves with solid financial advisors and still approve every expense 15 years later.

Sure, there were indulgences: season tickets, world travel, a nanny, a Range Rover, a Rolex. But daily life? Pretty normal.
Jacki shops at Target and TikTok Shop. She drives a Honda Odyssey. Their friends haven’t changed. They still love Outback (“Nothing beats a Bloomin’ Onion,” she jokes). Their kids only recently discovered their lottery story.

A Shift Into Public Service

Gil, a Navy veteran, eventually took his passion for helping others into politics. After Trump’s 2016 election, he felt pulled to step up. He served in Congress, worked as undersecretary of defense, and is now back on Capitol Hill.