A little friendly competition on the golf course has raised $285,000 dollars for nine local charities during one tournament. The Generosity Cup provided a fun day on the links in July at Red Sky Golf Club and encouraged people to be generous.

The Generosity Cup was started by Trey Little and Kyle Van. Little is the president of National Christian Foundation in Houston, which is a faith-based organization that helps people give to charities, ministries and churches.

“The National Christian Foundation has what they call “Generous July” but it’s quite hot in Houston this time of year, so 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.”

“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. So, I texted eight people from different local charities that I knew that night. Within 24 hours everybody said, ‘Great idea’ and we started with those eight charities,” Van said.

Van initially thought they could raise $20,000 or $30,000.


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“But then a friend of ours, Barry Davis, who is involved with the BetterMan, a charity based out of Dallas but they have an organization here, too, said, ‘why don’t you go for $75,000 or $100,000?’ So we had eight foursomes for each charity, and some independent teams, so 12 teams total, and we played Red Sky Golf Club,” Van said. “We ended up with $137,000 bucks and I thought, ‘Well, I guess this thing’s going to work.”

Golf legend Tom Watson, center, took time to pose with every team in the Generosity Cup Tournament before play began. Generosity Cup/Courtesy photo

This summer, the charities expanded to nine.

“One of our friends, Eric Reinhardt, asked if we could add one more charity and he is involved with Junior Achievement and that fit our model so then we had two teams per charity for 18 teams and four independent teams for 22 teams total and Red Sky Golf Club worked with us to take over the Tom Fazio course for the afternoon,” Van said.

The nine charities are:

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

“I really wanted people who live out here three to five months a year to treat it like home for three to five months a year. This is not vacation. This is home,” Van said. “What I’m sensing is a lot of our locals whether they’re from Florida or Arizona or Atlanta or whatever, are starting to say, ‘Hey, let’s get behind this because this is really helping support the Vail Valley. We’re helping support the people that support us here.”

Trey Little, left and Kyle Van are already planning next year’s Generosity Cup tournament at Red Sky Golf Club. Generosity Cup/Courtesy photo

The golf tournament started out with burgers and hot dogs and all the fixings at Red Sky Golf Club and the teams gathered on July 21. Little and Van explained the rules and introduced the nine charities and explained where the money raised was going. And then the crowd was treated to some insight and inspiration from six-time PGA Player of the Year Tom Watson.

“One of the teams was trying to recruit Tom to play with them, but Tom said, ‘Well, I just got back from the British Open so I don’t want to play but I’ll be glad to help anyway I can,’ so we were so thrilled to have him speak to the group and answer a few questions for about 30 minutes before the tournament started,” Van said.

Watson spoke about how he got into the sport and playing with his dad, who was a historian of the game. He also joked about how his mom would get telephone calls on the house phone from people like Arnold Palmer and Jack Nicklaus calling to play with him when he was a young rising star on the golf circuit. At the end of his talk, Watson stressed that it’s about having fun out there during the tournament that day. The PGA champion who won eight majors also took time to take a photo with each team before the tournament began.  

Fresh off of a trip to the British Open, American golf legend Tom Watson opted not to play in the Generosity Cup, but instead gave a talk before the tournament started at Red Sky Golf Club. Generosity Cup/Courtesy photo

Last year the event raised $137,000 and this year, the amount doubled.

“Our “stretch” goal this year was $250,000 and wow, the generosity was contagious and the support from our out of state summer residents who also call the Vail Valley home was spectacular,” Van said.

Evans Scholars won first place in a scorecard playoff with Young Life coming in second and the Eagle Valley Community Foundation finished in third place. Each charity was given at least $25,000 with the top finishers earning more.

“A huge thank you goes out to Trey Little and Kyle Van. It’s such a gift to the middle school and high school kids in this valley that will benefit from their generous hearts and the generosity of the donors.” said Ben Dodds, area director for Vail Valley Young Life. “There’s a lot of nonprofits in this valley and to see those nine charities be recognized at that course, on that stage, and to see the men and women in the room that just believe in the different nonprofits, whether it’s kids or helping veterans and all of the other organizations represented is a tremendous gift.”

“It’s super special as a nonprofit to be invited to participate in this,” said John Welaj, executive director at Habitat for Humanity Vail Valley. “We already collaborate with all these charities, so it’s nice to be here together, meeting new people that we have commonalities with and that has a ripple effect through our community, it doesn’t just end necessarily in one day. There are a lot of opportunities to help each other out because we’re doing a lot of the same work. And it’s kind of cool to see it all kind of come together in this manner thanks to the Generosity Cup.”

Little and Van are already planning for next year with the Generosity Cup scheduled for July 20, 2027.

“I feel like we’re all very blessed to be a part of this and we’re excited for what’s to come. A big thanks to Red Sky Golf Club, they have been wonderful to work with, and we love our 88 players and the charities. The heart behind this is to have one event that can do so much for all these charities,” Little said. “That would not have happened if the 88 people that played did not say, ‘I’m in.’ We are better together, and it’s the 88 people who came together and said, ‘I want to be a part of something bigger than myself, and I want to be a blessing to nine charities in the Vail Valley.’”