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PENSACOLA, FL – On Saturday, August 29, 2026, Aaron and Kimberly Watson accepted the 2Wins Excellence Award on behalf of the Watson Family Foundation at the 4th Annual CommUNITY Gala, hosted by 2Wins, Inc., a Pensacola nonprofit devoted to mentoring and empowering at-risk youth. The award was presented by the organization's founders — President Jerimey Tart, Vice President Jermaine Tart, and Executive Director Neal Croom, Jr. — before a room of community leaders, sponsors, families, and young people at the Museum of Commerce in downtown Pensacola.
A Night for Escambia County's Young People
The CommUNITY Gala is 2Wins' signature annual event, and it is exactly what its name suggests: a celebration of unity, resilience, and progress in Pensacola. Held this year at the Museum of Commerce at 201 East Zaragoza Street, with doors at 6:00 p.m. and the program running from 7:00 to 10:00, the evening brought supporters from across Escambia County together for dinner and drinks, a prize raffle, and an honest look at the work 2Wins does the other 364 days of the year.
Donte Sheppard served as host, keeping a full program moving without ever letting the room forget why it was there. The keynote was delivered by Pensacola attorney Troy Rafferty, who spoke about the importance of investing in young people and about his work representing survivors of abuse at the Dozier School for Boys.
2Wins, Inc. describes its mission plainly: building a brighter future for at-risk youth in Escambia County and the surrounding areas by providing, through mentorship, education, and community engagement, the tools and opportunities young people need to succeed and thrive in every aspect of their lives. That is unglamorous, long-horizon work — showing up for a kid consistently enough that it changes the arc of a life. The gala is what funds it, and it does so in a room where the young people being served are present, seen, and celebrated.
Honored in Good Company
The Watsons were recognized alongside a group of leaders and organizations whose work reaches Escambia County families every day: Governor Williams; the Escambia County Children's Trust, whose investment in local children's services reaches families across the county, represented by Lindsey Cannon, Maureen Gibbs, Demetrius Rowland, and Kim Cox; and Hassan Hill, founder of Youths Left Behind, who delivered the keynote at a previous CommUNITY Gala and whose work guiding young men toward accountability and growth has become a fixture of this community.
Past honorees include Bryan Freeman, the 2025 CommUNITY Award recipient, recognized for his leadership and service to Pensacola.
What the Excellence Award Recognizes
The 2Wins Excellence Award is presented during the CommUNITY Gala to individuals, community partners, and organizations that demonstrate outstanding service, leadership, and a commitment to empowering local youth and families. It is, in other words, an award about follow-through — not about a single night, a single donation, or a single good intention.
The Watsons were recognized for the work they do through the Watson Family Foundation, the family's vehicle for direct, practical investment in Pensacola families. That work includes:
- Juneteenth: A Family Reunion for the Culture — the Foundation's annual festival at Museum Plaza, a free, family-centered celebration that has become a fixture of Pensacola's summer and a reminder that history is best taught in community, out loud, with music and food and neighbors.
- Laptop giveaways — putting computers directly into the hands of local students, because a kid without a device is a kid doing homework on a phone.
- Hardship support and relief — direct assistance to families navigating an unexpected crisis, the kind of gap that rent-and-groceries math cannot absorb on its own.
- The 1,000 Turkey & Grocery Giveaway — one thousand turkeys distributed to Pensacola-area families at the holidays.
Kimberly Watson serves as President of the Watson Family Foundation and is the driving force behind its programs. Anyone who has watched her build the Juneteenth festival from the ground up each year understands that Saturday night's recognition was a long time coming.
Aaron Watson, a Pensacola attorney, co-founded the Foundation with Kimberly and works alongside her on its programs. Alicia Waters, Administrator of The Watson Firm, volunteers with the Foundation, as do a number of others who give their time throughout the year.
The through-line is not complicated. Every one of these programs starts from the same place: a family in Escambia County needs something concrete, and somebody decides to actually get it to them.
In Their Words
Accepting the award, Aaron Watson thanked Jerimey Tart, Jermaine Tart, and Neal Croom, Jr. by name, credited the mentors who do the daily work, and turned the recognition back toward the young people in the room.
Kimberly Watson expressed her gratitude for the honor and for the community partners across Pensacola whose support has made the Foundation's work possible.
Thank You to 2Wins — and to the Sponsors Who Fund the Mission
An event like this does not happen on goodwill alone. The 2026 CommUNITY Gala was made possible by a long list of Pensacola businesses and organizations that put real dollars behind youth mentorship, including Youths Left Behind, 100 Black Men of Pensacola, Epilepsy Alliance Florida, the Pensacola Breast Cancer Association, Changing The Narrative, Thru Trauma to Triumph, Peculiar Images, JM Productions, Serenity Flow Yoga, Ruff Path, Wilmer Financial Group, BlueWind Technology, Mitchell Legree Flooring, Boneface Tattoo Shop, Superior Dream Travel, Casks & Flights, Brunchella, Epic Sweets & Treats, Thompson Smoked Sausage, Sonny's BBQ, DJ Cracee, Durpul, D & D, and Walmart.
Thank you as well to Jerimey Tart, Jermaine Tart, and Neal Croom, Jr., and to the 2Wins board, staff, and volunteers who spent months planning an evening that felt effortless from a seat at the table — and to Donte Sheppard for hosting it.
How You Can Support 2Wins
If reading this made you want to do something rather than just feel good about it, 2Wins makes that easy. Sponsorship for the CommUNITY Gala begins at the Friends of 2Wins level at $750, which includes two entry tickets to the gala, recognition on the 2Wins website as a community supporter, and acknowledgment at events. Higher tiers — Title, Impact, Champion, and CommUNITY — carry expanded recognition for businesses that want to align themselves with the organization's mission.
Tickets, tables, and sponsorships are treated as charitable contributions supporting 2Wins' youth mentorship programs. Learn more, reserve a table for next year, or become a sponsor at 2wins-npo.com.
Mentorship is one of the few investments in a young person's life that costs comparatively little and compounds for decades. Escambia County has an organization doing it well. It deserves the room's full support, not just its applause.
About the Watson Family Foundation
The Watson Family Foundation, founded by Aaron and Kimberly Watson of Pensacola, invests directly in Escambia County families through its annual Juneteenth: A Family Reunion for the Culture festival, student laptop giveaways, hardship assistance, and its 1,000 Turkey Giveaway. Learn more here.
About 2Wins, Inc.
2Wins, Inc. is a Pensacola nonprofit committed to building a brighter future for at-risk youth in Escambia County and the surrounding areas through mentorship, education, and community engagement. Learn more at 2wins-npo.com.