How Sports Philanthropy Is Changing Lives Beyond the Game | Roy Kessel

Welcome to the Legacy All-Stars Podcast. We feature inspirational stories from people who dedicate themselves to helping others.

Here is your host, Alan Pavlosky. All right, everybody. Welcome back to the Legacy All-Stars Podcast. I'm your host, Alan Pavlosky. And today we're talking about something that sits at the intersection of sports, service, and community impact. My guest today is a friend of mine who has built something rare. Roy Castle is a sports attorney, former NFL agent, and the founder of the Sports Philanthropy Network, an organization dedicated to educating, connecting, and elevating the nonprofits, athlete foundations, leagues, and organizations that use sport as a vehicle for social good. Roy launched SPN in 2019, and what started as a vision for more unified sports philanthropy community has grown into a national network with chapters, podcasts, a sports philanthropy academy, and one of the most compelling annual gatherings in the space, Sports Philanthropy World. In 2026, that event comes to Washington, DC from August 3rd through the 5th. And today we're going to dig into why it matters, who should be there, and what's at stake for the future of sports-driven impact. Roy, great to see you as always, and thank you for coming on Legacy All-Stars.

Alan, thank you for having me. Excited to be here and excited to have you involved with our conference as well.

I'm looking forward to it, and we'll talk more about that. But I'm very excited about being part of the conference. Roy, for those who are not familiar with Sports Philanthropy Network, how would you describe what SPN does and the problem it was built to solve?

Yeah, I think the first thing that we talk to people about is that everything we do is about changing lives and transforming communities through sport. Sports has an innate power to make a difference really a few ways. One is to bring people together. We see what's going on with the World Cup in the country right now of what a unifying force sports can be. The second is to break down barriers, right? You see conversations going on, and the World Cup is a perfect example, in and around countries that normally would not allow themselves to have dialogue or to spend time together. So those are really two important points, and what we focus on our three core constituencies, which is athletes and their foundations, community sports nonprofits, and then larger sports organizations like teams, leagues, governing bodies, associations, universities. And we look at how can we leverage the power that each of those groups have to put their forces together for good. And that's really what the vision was, was recognizing that athletes have a strong desire to give back and to help their communities. But sadly, in a historical perspective, they've been given very little guidance and support in order to accomplish that. And, and what we would typically hear is their agents, their wealth managers giving them advice and telling them, hey, here's how you make a difference in the world. Number 1, you sign autographs. Number 2, you take photos with people. Number 3, you plan golf outings. And number 4, you go to fundraising dinners. And you've certainly been around all of those things, Alan, and seen it many, many times. And, and the sad part is that's really a disservice to these athletes, men and women that have reached the pinnacle of their sport. You don't get to be a pro athlete in any sport by mistake. This is something that takes an enormous amount of commitment and dedication. And so relegating them to kind of being celebrity figures without any substance is really a disservice to what they are and what they care about.

Yeah, absolutely. You spent over 25 years as a sports lawyer and an NFL agent before launching SPN in 2019. What was the insight or moment that made you say this community needs to exist?

Yeah, I think the trigger for me was probably running a celebrity golf event for an NBA player that was based here out of Chicago that brought in a lot of these high-level players. And in organizing that event, right, you now become a peer level to these all-star NBA players. We were hosting one of the league-sanctioned summer all-star games that they allow. So, we did it at the United Center. We did it at Allstate Arena in Chicago. But you would be sitting there with those players throughout the weekend at the dinner, at the golf outing, at the celebrity game, and hearing their passion and then asking That's great. What are you doing about it? And kind of getting a shoulder shrug of like, yeah, I don't know what to do. I only do what my agent or my attorney tells me to do. And so sadly, many of the players are getting bad advice or no advice at all, and they're not using their platform to articulate the things, to take a stand. Right. This was before the advent of social media. And so now it's a little bit different because players recognize. I can jump on Instagram, I can jump on Twitter, I can throw out my opinion, right? For better or for worse, some of them harm their images that way, but they have a voice. But back in the early 2000s, this didn't exist. The players were looking for where they could make an impact, and they were looking for help. They really were seeking it out because they bounce around from celebrity basketball game, celebrity golf outing. But that's not really where the hard work is done. That's not where you change lives and transform communities.

Yeah. I want to dovetail that into a question. You and I have had these conversations for many years. And one of the things that you and I are both passionate about is to figure out ways to communicate effectively to athletes that they don't have to start their own foundation. In order to succeed at making an impact. There are so many other vehicles and ways that they can structure their philanthropic activity. Let's talk about a few of those briefly before we move on to the next question. One, we've talked about fiscal sponsorship, and I'm going to let you lead this, but please share with us ways that athletes can make a difference that aren't necessarily starting their own 501.

Yeah, and that's a great point. So we often— talk athletes out of starting their own foundations. In many cases, I feel we talk more of them out of starting a foundation than into starting a foundation, because we've seen the need for athletes that want to make a difference. When you start your own foundation, if you set up your own 501, you have substantial legal, financial, and reputational risk that's aligned with that foundation. Even if you as the athlete do nothing wrong, if somebody in organization does, the headline and the ticker on ESPN or in the Boston Globe or on FS1, right? Those are all going to list the name of the athlete because that's what gets the eyeballs. And the sad part is these are all— we've seen almost no instances of intentional malfeasance where an athlete is using this by design for improper purposes. Usually it's sloppiness. It's inappropriate professional services that just don't dot the i's and cross the t's for the work that's being done. So as you mentioned, a fiscal sponsorship really allows an athlete to run the elements of a foundation that they're interested in. Maybe it's a golf tournament, maybe it's a gala, maybe it's a football or basketball camp. They can do all of those things under the banner of a parent nonprofit, a parent 501 that can handle all the back office functions. They can raise the money, but they don't have to incur the costs, the staffing expense, the infrastructure that would be needed to have their own 501. Fiscal sponsorship is a very—

and the compliance responsibilities, for sure.

Absolutely. Compliance— people don't recognize that, uh, you've got to register in about 42 states in the United States to accept charitable. So if you're really, let's say, an NBA player, MLB player, and you're traveling around the country and you're doing activations as you move around, you're touching people in a lot of different states. You're not just a local nonprofit that in your case could comply with California, or in my case could comply with Illinois and be okay.

Yeah. One of the other things you and I have had long discussions about is that athletes can also tie their name to a cause that already exists. There's hundreds and thousands of causes that are amazing and doing a great job of servicing the people in need. But athletes can offer to lend their name and likeness to those causes. That's another really powerful way to do this.

Yeah, and I think that what people miss in that perspective is from an efficiency perspective, right, from a sort of economy of scale, setting up your own new business, because a nonprofit is still a business, it's just a nonprofit business. You know, you can use an example like McDonald's. If you wanted to own a hamburger chain, to try to set up a hamburger chain that can compete with McDonald's on a one-off is very difficult. To connect and dial in and say, I'm going to lend my voice, I'm going to lend my name recognition, my platform, and I'm going to do it Special Olympics. I was at American Cancer Society breast cancer event yesterday. There's incredible orgs out there. Some do better work than others. I always say there are no bad causes, so you just have to select and do a bit of research and due diligence and identify the organizations in the cause that you care about in that sector and find the ones that are doing the best work that you can partner with.

Yeah, for sure. That leads me to my next question, which dovetails perfectly. What does it look like when athletes, nonprofits, leagues, and foundations aren't connected to each other and learning from each other? And what opportunities get missed? And specifically, what does SPN do to help that process?

So I'll start at the end. One of the best things that we do is host Sports Philanthropy World Conference and bring people together. When we host events either locally or regionally as well, the best feedback that we get is that we cross those different constituencies and mix them together. So instead of everybody staying in their lane or in their channel or bucket or whatever people want to call it, we get a lot of response that teams in particular, right, will stay within their league, stay within their sport— MLB and baseball, NFL and football, right, NBA basketball, etc., etc. And what they're not doing is they're not learning from other organizations that are facing different challenges. Those challenges can be on the level of fundraising. Those challenges can be on some of the economics of the sports world, which we've seen enormously. Again, touching on the World Cup, the cost of soccer, youth soccer in the United States has escalated completely out of control and disproportionate to what is needed for most kids to be able to play and participate, right? Very few are going rise to an elite club level that needs that premium travel expense. But what we see, and one of the reasons we exist, is how do we bring people together to break down those silos and have conversations cross-sport, cross-league. And we're very proud of the fact that when we have our conference, we get a wide geographic base, but we also bring in local community nonprofits, colleges and universities, national nonprofits, professional sports teams, leagues, governing bodies, players associations. We get those different perspectives. So when you're in the room over the course of those few days, you have an opportunity to really learn from others in this sector, but that are in a different part of the sector. And one of the things that we're most proud of is that the speakers at our conference stay and participate in the conference. They're not hired guns coming in to speak, give an hour presentation, and leave. They're people that really believe in this community, want to do good, and they look both directions. They look for people that can help them build and grow their organization, as well as looking at individuals that they can mentor and nurture and organizations that they can support.

Yeah. You and Sports Philanthropy Network have worked with athlete foundations and nonprofit leaders on capacity building, fundraising, board development. What are the most common gaps you see in sports-based philanthropy organizations?

Well, I think the unifying gap is usually money. Every organization is looking for more money, and the organizations that have the money are looking at how they can be more focused and more effective with the distributions and grants that they're making. One of the things that is very hard is finding meaningful ways to measure the impact, because at the end of the day, a million dollars into a program is not the same as a million dollars into another program. You want to look at what impact is coming out of this, and that is a significant challenge. We see, in my view, too much duplication of effort and resources. So for example, too many people trying to run, let's say, a literacy or financial literacy program alongside their sports nonprofit, but instead of working together and collaborating with existing and proven programs in those spaces, they may try and develop it on their own. And so if Alan tries to do that, He's gonna spend more time, money, and effort. And in all likelihood, because you're not a curriculum specialist or you're not a literacy or financial literacy specialist, you're going to come up with an inferior product. So how do we help matchmake organizations to the people who have successful tools and resources that can help those organizations provide the programming elevate their fundraising, do a better job training their board of directors, things of that nature.

Yeah, and more importantly, become more efficient so they're not spending money on things they don't need to spend money on. More of that impact can go directly to the impact that they're trying to have on communities.

Yeah, I think that's one of the challenges that we've seen with the funders, and it's coming around now. Historically, funders were very reluctant to put money into infrastructure or technology or those kind of resources. We see today how quickly technology moves and changes. If you don't arm your nonprofit organization with the tools and people who have the skills to utilize those effectively, right, AI being the one that's on the table most currently now, it really creates a bad flow for the organization because we're now getting behind what other people are doing in our same space, in our same sector. And so funders are starting to realize, yeah, we don't want 80% of the money going to infrastructure and technology, but we have to allow a percentage of that budget, and we have to get away from the 990 metric mentality of How much of it is going to programs? Because I can't run the programs effectively. I can't maintain the connection to my youth, to my constituents if I'm not tracking things properly.

Yeah, for sure. All right. I really want to dive deeply into Sports Philanthropy World 2026. The event is August 3rd through the 5th in D.C., as you've stated so kindly. I will be there participating. I love this. Can't wait to make an impact. The agenda includes a community service project, keynote sessions, a pitch competition, sports philanthropy awards, and a youth philanthro-fest. Walk us through the highlights and what attendees can expect on each day and who should attend, Roy.

Yeah, in terms of who should attend, I think we've really been successful at building a diverse attendee base. And so by that, we have professional athletes, we have people from pro teams, leagues, and governing bodies, and universities, universities. We have more funders. We've made a concerted effort to reach out and engage more funders, more family offices, venture philanthropy, wealth managers, philanthropy consultants, right? The groups that have the funding. This year we added on in particular a funders forum, which is going to be invite-only for those groups, the ones that are giving out the money, so that they're in an environment where it's not feeding frenzy on everybody trying to beg them for funding, but where they can really talk about and address the needs that, that sector, that component of the sports philanthropy sector has in terms of identifying and deciding where the money is going to go to and how it can be done most effectively. But from a schedule perspective, as you said, we're going to start Monday with a service project in DC. Monday night, we'll move towards our opening reception, and then we're really excited this year to add a pitch competition. Um, that's new for us. We just closed the application window. We've got a deadline of July 3rd to name our 10 semifinalists, and then July 15th we'll name the finalists that will be pitching at the show. We've assembled a committee of people that have experience running pitch competitions to interview and review the applications so that we can have very engaging groups that are going to do a terrific job at the conference. On Tuesday, we've got a full day of programming. We're happy to be hosted by George Washington University, who has a sports philanthropy certificate program. Shout out to Lisa and, and her group that have always been great allies for us from day one of Sports Philanthropy Network. Lee Steinberg is going to give a keynote presentation during lunch. We've got an owner's panel after lunch. We've got owners that are going to be involved. Bob Castellini from the Reds confirmed that he will be there, as well as some other invitations that are out. We always strive to make sure that our events are diverse, not only in gender and race and organizational size, but geographic location. We get people from all over the country. We've had organizations from around the world participating. Tuesday night, we're launching the Sports Philanthropy Awards. We've got 36 categories that have been identified because we believe that there needs to be more recognition of the amazing work that's going on in this sector. We're also debuting our Hall of Fame, our Sports Philanthropy Hall of Fame. Is going to have his first inductee at the event on the Tuesday night, August 4th. And then Wednesday will be approximately half day of formal programming, and then the afternoon will be workshops, roundtables, and that Funders Forum alongside that Youth Philanthrofest. The Youth Philanthrofest is a new initiative that we've added this year, and the primary motivating— is we want the youth that are involved in so many of these sports initiatives to recognize that they're not stuck for life in a role where they have to be a recipient or a beneficiary of these services. We want them to set their vision higher and chart a course where they recognize they have the capacity to give back. They have an ability to make a difference. And maybe they can't give millions of dollars, but they can give their time time, money, and effort into supporting different causes. And they can do that from a very early age.

Yeah, I love that. And, you know, you and I've had many discussions about this, and my thesis is that athletes that participate in philanthropy inspire others to give them permission to feel like they can make a difference too. And I think I've had multiple conversations with athlete clients of mine and friends that said to me, you know, I was inspired by somebody else to make a difference early on in life. And this is the kind of power that the industry has and athletes have to inspire others to make a difference. So I love the Philanthrofest idea. I think it's just going to be a wonderful aspect of the event. I just really like it.

Yeah, I think you hit it right on the head, Alan. And I know that's an area of passion for you and the topic for the panel that you're going to host at Sports Philanthropy world, I think that people don't necessarily understand the power that setting an example has. Because when you teach somebody, it doesn't matter where you came from, it doesn't matter what you started with. When you look at people's backgrounds, it's the proverbial image you see on social media a lot with that tip of the iceberg, right? We see the tip of the iceberg. But we haven't seen all the hard work, all the sweat, all the hours that go into developing a business or an organization. And so we don't know when we see a highly successful athlete on the football field, the tennis court, the basketball court, baseball field, wherever it is, we don't see everything that they've been through in life. We see their success, right? Maybe we see their failure at that point too, because there's always Nobody goes through life unscathed, and especially in college and professional sports, you're going to have high-profile failures if you're there. But you don't know what somebody's overcome to get there. And so looking at them in that community, one of the things that I've often said to athletes is they don't realize how high they are and how great of an impact they can have because in their world they only look up, right? I call it the king of the mountain syndrome, right? They're not the king of the mountain, right? They're not Tom Brady or Peyton Manning or Aaron Rodgers. They're not LeBron James or Wemby or whoever the elite athlete is at a given time in a given sport. But when you're playing a professional sport, you're higher than almost anybody else will ever be in that sport. And so when you look backwards and look at your trail and your legacy, and you start going back to your college, you start going back to your high school, you start going back to your neighborhood, these are all people that will look up to you. You don't have to be the top of the mountain, the king of the mountain in your sport. You're in the major professional league, people will look at that. There will be signs at your high school. There'll be kids growing up going, you know, "I know that, you know, we went to that high school." Yeah, for sure.

When you look across your network and the organizations doing this work, what are the most impactful areas where sports philanthropy is really making a difference?

I think the things that we're hearing the most right now are mental health and financial literacy, and brain health and concussions. Those are the 3 big areas where there's a great need, right? Health and wellness, a combination of all kinds of things where you look at wellness and it's really mental health, spiritual health, physical health, financial health. All of these things flow together. But how can we work as an organization as a community, as a network to help everybody deal with those particular issues. One of the challenges that we see is that there's really not a consistent theme, right? So there, we talked about overlapping resources. There's gotta be 50 organizations out there dealing with mental health and similar number dealing with financial literacy. Some of them are better better than others, right? The concept is important. I'm not saying that we want one that's the be-all and end-all. You're never going to have a perfect program. But I do think that it is important for us to look around and say, hey, here's what we want to be able to do, here's how we want to be able to do it. And I think it's critical for us to put our heads together as a community and attack these issues. Mental health isn't comprised of one single factor or one single program or training. It's a recognition with the community that this is something we need to deal with every single day.

Yeah, fantastic. Well, I would be remiss if I don't ask you a legacy question since this is Legacy All-Stars. When you think about legacy, your own and SPN's, what do you hope this network ultimately represents 10 or 20 years from now?

That's a great question, and we talk about it frequently as we work with people to build out what we call a legacy blueprint. From our perspective, we want this legacy to be an organization that grows and touches every sport in every community. When we launched We had inquiries from organizations in 87 countries that wanted to participate in our first conference, which was amazing. That was really eye-opening to see the desire to do that. I've had a chance to go to Europe and speak on CSR issues in different countries. And I think what we've seen is that this is a global desire. Sports brings people together. I think the legacy that I would love to see is that this organization continues to grow, that we expand programming to Europe and to other continents, and that really, in a huge vision, I would like to see Sports Philanthropy World become akin to Fashion Week or Tech Week in Vegas or New York, where you're bringing together all of the different organizations and you have programming from from many different groups that are coming together. I don't believe this space should be owned by any one organization or company. I think that it needs voices, it needs opinions, it needs perspectives from youth sports, college sports, high school sports, pro sports, the philanthropy sector, community foundations, family offices, right? All of these different perspectives They each have a unique role in the ecosystem, and we want this to be a home where everybody feels safe and comfortable and able to contribute.

Yeah, that's fantastic. Well, we've come to the end of the episode. Roy, thank you. The work you've built with Sports Philanthropy Network is proof that sports is far more than what happens on the field. It's a platform for healing, opportunity, access, massive change. For our listeners, whether you're an athlete with a foundation, a nonprofit leader looking to grow your impact, or someone who simply believes in the power of sport for good, I highly encourage you to learn more about the Sports Philanthropy Network and to put Sports Philanthropy World 2026 on your calendar, August 3rd through the 5th in Washington, DC. And we'll have a link in the show notes for people to get more information. About that. I'm Alan Pavlosky, and this has been another episode of Legacy All-Stars, where purpose-driven people come together to share their story. Roy, I will see you at Sports Philanthropy World. I'm looking forward to it. Thank you again for coming on the show, Alan.

Thank you for having me, and for all of your viewers and listeners, just want to remind everybody to live generously.

That's awesome. Thank you, Roy.