At Your Service

The Kentucky Derby Ambassador Program Crafts Memories for a Lifetime

Written by Laura Ross

Everyone has a great Kentucky Derby story or two. Or, in the case of Kentucky Derby Ambassador Program mainstays Louis Waterman and his wife, Leah Brown, the count is in the hundreds. “I’m not the most knowledgeable horse racing fan out there, but I love the Kentucky Derby, the Kentucky Oaks and I love Churchill Downs,” explains Louis Waterman. “I just think that it is unbelievable that once a year, the entire world looks at Louisville, Kentucky, and we have this icon. It is just an amazing event and week.” 

Brown agrees. “Louis has shared his love of this with me, and now it’s in my blood too. It is an honor to be able to represent Churchill Downs and the Kentucky Derby to people from all over the world. They trust and rely upon us to take care of them at a very important moment in their life.” 

Since 1988, the Kentucky Derby Ambassador Program has paired trained, local volunteers passionate about the Derby with special guests and VIPs, including horse owners, trainers and families; celebrities; presidents and royalty; corporate sponsors; and more. The ambassadors act as guides around the labyrinth of Churchill Downs as personal liaisons and help navigate an incredibly complex array of details that go into making their guests’ visit to Louisville flawless. 

The takeaway? A lifetime of memories curated with ever-changing events, mishaps, celebrations and bucket-list moments. 

“As my wife will tell you, I’m a social butterfly,” laughs Waterman. “It’s been a great way to meet lots of really great people and be involved at a level where I would not have been involved before.” 

Waterman joined the fledgling group of original ambassadors in 1992 after an invitation from his friend, Newton McCravey. “That’s a little over 30 years now,” he adds. “The only Derby I missed was in 2017 when my daughter had the audacity to graduate from college on Derby Day. I just love this opportunity, and I love the Derby. They will someday have to take it away from me, kicking and screaming.” 

The essence of the Derby is in Waterman’s blood. Not only has he been a Churchill Downs ambassador for decades, he’s also given 30 years of volunteer efforts to the Kentucky Derby Festival, the annual month-long celebration that leads up to the Run for the Roses. He began as a community volunteer with the Festival and moved up the ranks to serve on the Board of Directors, where he has served as a member of the Executive Committee and former Treasurer. Recently, he was named Chair of the 2026 Kentucky Derby Festival, where he will oversee more than 70 major events. “I am filled with Kentucky Derby Festival pride and wonder,” Waterman says. “I am both excited and nervous about having a more impactful role in bringing the Festival to the community. Seeing the smiles that are made, the awe that is inspired, the city coming together in celebration and the opportunity for all of us to forget about our worries for a couple of hours or weeks each Spring is priceless!” 

“There is no way to fully understand the work that the ambassadors do until you actually get in there and do it,” says Brown. “It’s one of the hardest working groups of people that I know and they love the Derby and the experience of being there. We have amazing access to Churchill Downs. It’s not unusual to end Oaks and Derby with at least 50,000 steps on your pedometer. It’s constant movement and organized chaos of the best kind.” 

The lively atmosphere energizes the dynamic couple, who lead equally demanding professional lives throughout the rest of the year.

Waterman is a Louisville native, a former Jefferson Circuit Court Family Division 4 judge and a leading family law attorney and partner at Goldberg Simpson LLC. In addition to a busy career, he has served on several boards and acted as trustee for multiple organizations. He is the past Chair of the Jewish Heritage Fund for Excellence; a former Vice Chair of the Louisville Zoo Board of Directors, where he also served as general counsel; and past Chair of the board of trustees of the Bingham Clinic. 

Brown is an Executive Life & Leadership Coach with over 30 years of experience. She is the owner of a boutique coaching and consulting firm in Louisville, Kentucky, providing individual coaching, leadership team coaching and customized training programs for teams at all levels. Selected and trained by Dr. Brene’ Brown, she is a certified Dare to Lead™️ Facilitator and a certified Simon Sinek WHY Coach with Simon Sinek’s The Optimism Company. She is a certified DISC and EQ provider, Red Team Strategic Thinking Coach, Trainer and Instructor, Dale Carnegie Trainer, faculty member of the U.S. Chamber of Commerce Institute for Organization Management and Instructor for the University of Louisville College of Business Executive Education Program. She is also one of the only certified Divorce Coaches in Kentucky.

Being a Kentucky Derby ambassador has been an extraordinary experience for Waterman.

“I had the privilege of being an ambassador for William T. Young and Ambassador William Farish, former U.S. Ambassador to the United Kingdom.” It was due, in part, to Waterman’s υ
assignment with Ambassador Farish that he was later asked by Churchill Downs to host and escort the Queen of England when she and Prince Phillip came to the Kentucky Derby in 2007. “The Queen told me that coming to the Kentucky Derby was a “bucket list” trip for her,” Waterman said.

Waterman has also been an ambassador for three U.S. Presidents; President George H.W. Bush, President George W. Bush and President Donald Trump. 

“Leah and I have been fortunate to become very good friends with some of the people we’ve hosted throughout the years. We have traveled with some, visited some at their homes and a few even came to our wedding. We’ve been extremely fortunate in that realm,” says Waterman. “How does a kid from Louisville, Kentucky, get to do this kind of stuff?” 

Waterman and Brown have also hosted Hollywood and music royalty. “One of the funniest moments happened when I was asked to pick up a guest and escort him to another location,” Waterman explains. “The only thing I’d been told was that his name was Justin. He had two sheriff’s deputies with him, but I didn’t think much of it. I asked him to stay close and not to stop as we moved through the crowd.”

“As we walked out, the crowd went wild! A photographer, loaded down with cameras, was standing on a trash can trying to get a good shot when he started to fall. I instinctively reached my hand out to stop him from landing on top of us,” he recalls.

The next day, Waterman awoke to see the cover of the Lexington Herald-Leader with a picture of Justin Timberlake and Waterman manhandling the photographer, with the caption, ‘Justin Timberlake’s handler holds back the paparazzi.’ Waterman laughs, “I got an immediate call from my then teenage daughter who says, ‘Dad, you were with Justin Timberlake!’ and I replied, ‘Who is Justin Timberlake?’ and she pointedly said, ‘Dad! You’re a loser!’ and hung up on me.” 

When Waterman and Brown first started dating, she loved his Derby stories and the pictures that went with them. “Louis’ office is covered with photos of the celebrities and dignitaries he’s met and hosted over the years,” says Brown. “Once, he mentioned knowing Bo Derek. I immediately said ‘You don’t know her! There’s no picture hanging in your office.’ He said, ‘Yes, I do. I’ve just been too chicken to ask her for a picture.’ It became a longstanding joke between us. Louis claimed he knew her and me, swearing he didn’t. That is, until 2017, when we were in Del Mar at the Breeders’ Cup. We were walking down the chute toward the Paddock when, suddenly, three beautiful blonde women walking toward us shouted, ‘Louie! How are you?’ It was Bo Derek and her sisters,” laughs Brown. 

Several years later, Brown happened to be on a flight home from Dallas and ran into Bo sitting across the aisle from her, heading to Louisville, where she was working on a film with John Voight. It just happened to be Thunder Over Louisville weekend, and the Waterman’s, along with Mike Shea, 2022 Kentucky Derby Festival Chairman, escorted Derek to the fireworks and festivities of the premier event leading up to the Kentucky Derby.

While rubbing elbows with the rich and famous is exhilarating, it’s also a lot of hard work. Kentucky Derby ambassadors devote round-the-clock hours to their work and are constantly on the go, managing every possible detail for their assigned guests. 

“There’s a great deal of responsibility that comes with it, because we’re with people who have sometimes spent their entire lives trying to reach Oaks or Derby, whether with a horse or for a once-in-a-lifetime experience,” says Brown. “It’s a very vulnerable position for them, and for Louis and me to be there in those high-stakes moments, building trust, guiding them where they need to go and taking care of whatever they need is incredibly important.” 

The Kentucky Derby Ambassador Program was modeled originally off a similar program developed for the Calgary Winter Olympics. Tom Meeker, former President and CEO of Churchill Downs Incorporated, was so impressed with the ambassadors at the Olympics that he came back and said, “We’ve got to do this for our Horse Owners at the Kentucky Derby.” Today, Janet Miller, Senior Manager of Sales Administration at Churchill Downs oversees the Ambassador Program with the help of Sara Ellis, Derby Ambassador Manager at Churchill Downs. The ambassadors are governed by an executive committee of which Waterman is a former chairman. Brown will be stepping into that role in two years.

Interested ambassadors are vetted in interviews by the Chairman, Vice-Chair and Churchill Downs representatives. “You need to be a servant leader,” says Waterman. “We aren’t polishing shoes or babysitting. We want you to serve our guests by being gracious and able to run with nearly any task, for any kind of person, at any time. You need to be flexible whether the person is famous, not so famous, local, international, nice or not so nice. However, everybody I’ve met, along this journey, with just a couple of exceptions, has been simply wonderful to know.” 

Brown adds, “We have around 70 ambassadors, and we’ve all had to learn the many changes at Churchill Downs over the last few years. The renovations have really changed the footprint of the track, and because we’re working with a crowd of around 150,000 people in one very compact space, the ambassadors must be able to turn on a dime. They must be able to move through crowds, move people out of the way and get people through. Our team is ready for anything and they accomplish it with such grace.” 

The ambassador training program begins months in advance of Derby. All the routes are memorized, the rules inhaled, and the trivia, backgrounds and who’s who of everything noted. Typically, the ambassadors kick into υ
gear on Opening Night (changing to Opening Day in 2026) at Churchill Downs, the Saturday before the Derby. “One of our first events is the post-position draw,” says Brown. “From there, we are on the backside every morning from Monday through Thursday, helping the horse owners navigate anyone who is coming to the stables to see their horse or watch them exercise.” 

Ambassadors spend many hours in the weeks leading up to the Derby getting a feel for the track and the frenetic flow of Oaks and Derby Days.  

“Many times guests arrive with last minute needs,” she adds. “Our job is to point them in the right direction with Louisville love and Derby hospitality.

Once the gates open on Oaks morning, it’s all-hands-on deck and the adventure is afoot. Armed with boundless energy, sensible shoes and a knack for making magic, the ambassadors will arrive close to dawn and usually not return home until close to midnight. It’s exhausting, but exhilarating. The friendships made along the way are priceless. 

“To me, it’s an honor,” adds Brown. “Every year is similar, and yet every year is different. The work the ambassadors do raises the level of the guests’ experiences, not just of the Kentucky Derby, but of Churchill Downs and the city of Louisville. Those are memories they will keep with them forever.” 

“It’s truly magical in meeting and becoming friends with people that you otherwise would have never met and never been exposed to,” muses Waterman. “They are some of the most delightful, phenomenal human beings you’ll ever meet. We’ve become friends and in some cases family, always looking forward to the next time we will see each other.” 

The planning? The hard work? The aching feet and dark circles under their eyes? The ups and downs, egos and excitement? It’s all worth it for Louis, Brown and all their fellow ambassadors. Waterman smiles, “It is worth it, because at the end of the day, you are the ambassadors. You are telling the story of Churchill Downs and the Kentucky Derby. Churchill Downs asks us to be our best; and we want to be our best for them. I think we hit the winner’s circle with that every time.”