Red Sky Golf Club Generosity Cup Raises $285,000 for Nine Local Charities

Aspen —The heat on the Tom Fazio course at Red Sky Golf Club in July was enough to make most folks seek shade, but the players on the greens were focused on something other than the temperature. It was a day of friendly competition, but the stakes were higher than a typical charity scramble. The goal wasn’t just to lower a score; it was to lift up the community.

That effort resulted in $285,000 raised for nine local charities.

The money didn’t just appear. It came from the Generosity Cup, an event that started with a simple logistical problem: Houston was too hot for a July golf tournament. Trey Little, president of the National Christian Foundation in Houston, wanted to move the "Generous July" campaign to a cooler climate where their donors were. He needed a venue and a co-pilot. That’s where Kyle Van came in.

“I had this idea to take Generous July on the road. Why don’t we go to Colorado, let’s go to where our people are?” Little said. “And then I said, ‘Why don’t we have a golf tournament?’ and that’s when Kyle stepped in with the idea to host it at Red Sky Ranch.”

Van’s initial reaction was skepticism. Another golf tournament? Really? But he saw a way to make it matter locally. Instead of just raising money for a general fund, he wanted local organizations to compete directly. He texted eight different local charity leaders that night. Within 24 hours, they were all in.

“At first I thought, ‘That’s all we need is another golf tournament,’ but why don’t we do something that would get the local charities involved where they would compete against each other and we could raise money for them,” Van said.

The early math was modest. Van and his team expected to raise between $20,000 and $30,000. They set up eight foursomes for each of the eight charities, plus some independent teams, totaling 12 teams. They played the course, they drank the water, and they collected the checks. They ended up with $137,000.

“‘Well, I guess this thing’s going to work,’ ” Van said.

The momentum didn’t stop there. The following summer, the scope expanded. Eric Reinhardt, involved with Junior Achievement, asked if they could add one more charity to the mix. The model held. They moved to two teams per charity, bringing the total to 18 charity teams and four independent teams, for a grand total of 22 teams. Red Sky Golf Club accommodated the growth by taking over the Tom Fazio course for the afternoon.

The beneficiaries were a cross-section of the local social safety net and civic infrastructure. The nine charities included the 4 Eagle Foundation, Ascend, the Eagle Valley Community Foundation, Habitat for Humanity Vail Valley, BetterMan, Evans Scholars, Junior Achievement, the Vail Veterans Program, and Young Life.

Golf legend Tom Watson even made an appearance, posing with every team before play began, adding a layer of prestige to an event that was fundamentally about grassroots giving.

The result of that expansion and the continued generosity of donors was the $285,000 figure. It’s a significant sum for a region where property taxes and cost-of-living adjustments are constant topics of conversation. But the organizers weren’t just counting dollars; they were counting engagement.

“We encourage people to get involved in their community, whether it’s their second home or primary, you still give back,” Little said. “You still have some skin in the game. I think that is really important and it endears them more to this area and they care about this community and these organizations.”

The event proved that you can scale up without losing the personal touch. By letting the charities compete, they created a narrative that was easier for donors to follow than a generic donation request. People didn’t just give to a cause; they gave to a team. And in doing so, they reinforced the idea that generosity, much like a good swing, is contagious.