By SFA Staff
Alexandria, VA – How do you raise enough money to fund hundreds of scholarships each year—and renew them year after year? That question sparked an idea in 1991 that would grow into one of Alexandria’s most beloved and impactful traditions: the Scholarship Fund of Alexandria (SFA) Gala.
What began as a modest gathering—“cocktails by Cassandra’s pool”—quickly evolved into a full-scale black-tie fundraiser, thanks in large part to founder Kitty Porterfield, whose vision helped launch the Scholarship Fund itself. In its earliest days, the impact was small but meaningful—just $7,000 in scholarships awarded in year one. Today, that number has grown exponentially, with approximately $700,000 awarded last year alone. In total, over $22 million has been awarded in local scholarships.
“That growth tells the story of this community,” said Executive Director Jasmine Milone. “Alexandria shows up for its students in a way that is truly extraordinary.”
The first gala, held under a tent at Cassandra Bradley’s West Braddock Road home, featured dinner, dancing, and a silent auction—elements that remain at the heart of the event today. Early organizers also established sponsorship levels and rallied local businesses to contribute, laying the foundation for decades of support.
By the mid-1990s, sponsors like Yates Automotive, King’s Jewelry, Virginia Power, and Inova Alexandria Hospital had joined the effort—many continuing their support in creative ways to this day. In 1996, the gala introduced a powerful tradition: a scholarship recipient speaking directly to guests.
“When you hear directly from the students, it changes everything,” Milone said. “It reminds you that this night isn’t just about a celebration—it’s about opening doors that might otherwise stay closed.”
The gala continued to grow in both scale and ambition. In 1999, Toyota became a major sponsor, and in 2008, the now-famous car raffle was introduced. Each year, Alexandria Toyota donates a vehicle and funds additional tickets for Alexandria City High School staff, giving participants a chance to win a car or a $25,000 cash prize—while supporting student success.
The event itself has traveled across Alexandria over the years, from Woodlawn Plantation to the George Washington Masonic National Memorial, before settling in 2004 at the Hilton Alexandria Mark Center. Today, the gala is a high-energy evening featuring a cocktail reception with multiple open bars, a gourmet dinner, silent and live auctions, and a lively paddle raise.
The paddle raise, sponsored by Burke & Herbert Bank, has become a defining moment of the evening, as more than 500 guests come together to give.
“This gala is where generosity meets purpose,” Milone said. “Every paddle raised represents a student’s future taking shape.”
Even during challenging times, the SFA adapted. When the pandemic forced the cancellation of the 2020 gala, organizers pivoted in 2021 to a fully virtual event, raising $450,000 through creativity and community commitment.
Over time, the gala has embraced innovation with digital bidding, online auction catalogs, and streamlined ticketing. Behind the scenes, a dedicated volunteer committee works year-round to bring the event to life—many members returning year after year.
The guest list reflects the breadth of Alexandria’s community—from business leaders and elected officials to educators, alumni, and longtime supporters.
Since its founding in 1986, the Scholarship Fund of Alexandria has supported more than 6,000 students and engaged over 16,000 donors, including more than 2,000 local organizations and businesses.
“Every scholarship represents a belief in a student’s potential,” Milone said. “And when you multiply that by thousands of students over 40 years, you begin to see the true impact.”
Now celebrating its 40th anniversary, the SFA continues its mission to support graduates of Alexandria’s only public high school, offering scholarships for college, career, and technical programs.
This year’s Gala & Auction will be held April 18 at the Hilton Alexandria Mark Center. For those who attend, it promises to be an unforgettable evening—but more importantly, it’s an investment in the future of Alexandria’s students. There are a few sponsorships still available as well as individual tickets. Visit alexscholarshipfund.org for more information.
