Chester Bishop has always been interested in politics. As a young boy in his native Jamaica, he wanted to be Prime Minister. After moving to the U.S., he ran for the City Commission of Hollywood. Just 21 at the time, Bishop lost that election and thought, “Maybe running for office isn’t necessarily for me.”
It would be more than 20 years before he put his name on another ballot, but his second election was a success. Bishop was voted onto the Board of the Florida HBPA in 2011, and has been a mainstay ever since. He currently serves as the organization’s first Vice President.
“I would go to the horsemen’s meetings and speak out,” he recalled. “I could see things going downhill at Calder and I wanted to see things get better – the racing, the facilities. People asked me, ‘why don’t you run for the Board?’ I ended up running and getting elected.”
South Florida racing has faced its challenges in the 10 years that Bishop has served on the HBPA Board, but there have been changes for the better.
“It was always a little more difficult working with Churchill Downs,” Bishop said. “We don’t always agree with the Stronach Group, but they are now the only game in town, and it has been easier to negotiate on many things. That has been the most positive change.”
Much of Bishop’s life has been dedicated to making things better for his community, but it took him some time to find his niche. He settled in South Florida in 1983, and soon abandoned a plan to attend veterinary school in Texas. It was one of many career paths he considered.
“When I was younger, when I was in middle school back in Jamaica, I wanted to be a farmer,” he said. “Then I wanted to be Prime Minister. When I came to the U.S., I did so many things. I drove a forklift. I went to school to be a travel agent. I took a course on becoming a paramedic. I wanted to be an accountant. I was all over the place.”
He sharpened his focus after joining the large law firm of Broad and Cassel. Bishop spent seven of his 12 years at the firm with their title company, and knew it was where he belonged.
“I found that I really loved the housing business,” he said.
Bishop finished college, earning a degree in business administration from Florida Atlantic University while with Broad and Cassel, and 20 years ago left to start his own title company, SuRealty Title, Inc. Not long after, he started looking for a way to give back to the community that had offered so many opportunities, and helped to start a non-profit for prospective home owners.
“Fifteen years ago, we started a HUD-certified housing counselling agency, which provides education for first-time home buyers,” he said. “We help close to 4,000 people every year to buy homes. We educate them on what it takes to qualify for a loan, how to find a realtor and a lender, we advise them about credit and home insurance and home inspections. The whole home-buying process is covered.
“We also do foreclosure prevention, and are working with Broward County on their rental and utility assistance program – we help people to get their rent and utilities subsidized,” he added.
Housing Foundation of America, Inc. is the largest non-profit in Florida providing home owner education, and one of only eight multi-state housing counselling agencies in the country after opening an office in North Carolina. Bishop now serves as Chairman.
With a growing business and his duties to the non-profit, it would seem there wasn’t much time for hobbies. But Bishop had developed a love of horse racing as a child that was rekindle in South Florida.
“My stepfather owned horses back in Jamaica,” he reminisced. “I was probably 10 years old, and one of his horses – she was named after my sister – won a stakes race. He gave me the trophy and the rest is history.”
A colleague in the housing business was married to a trainer based at Calder, and introduced the two. While visiting the Calder backstretch to meet with him, Bishop ran into an old acquaintance, Bobby Hale, who had trained for his stepfather many years ago. But Hale wouldn’t help Bishop get into racing.
“He told me, ‘Don’t get into the business, it’s too tough,’” Bishop laughed. “He didn’t want to train for me.”
Undaunted, he finally found a trainer and claimed his first horse in 1999. He won his first race with Mahogany Ship in 2000. His first graded-stakes victory would come the following year, but it didn’t come easy.
“I saw a horse in for $20,000, but it was Bobby Hale’s horse and I didn’t want to claim from him,” Bishop explained. “His name was Icanseetherain; he won pretty easily, and was claimed by someone else. I tried to buy a piece of the horse after he was claimed, but they wanted $100,000 for a piece of a horse they’d just claimed for $20,000. It was too much, but I really liked that horse. I had my vet check him out, and he told me, ‘don’t buy him, he has an ankle.’ I ended up buying 20% for $20,000.”
Icanseetherain was the second longest shot on the board when he was loaded into the starting gate for the 2001 Grade 3 Spectacular Bid Stakes, but he stalked the pace under jockey Jose Santos and got up in the final strides to win by a neck.
“It was opening day at Gulfstream Park, he was 48-1,” Bishop said. “It was one of my best days in racing.”
Blue Pepsi Lodge proved to be another astute claim. Haltered for $25,000 in October of 2007, the Florida-bred went on to win seven of his next nine starts, including three stakes races, and set a track record of 1:04.05 for 5 ½ furlongs on the dirt at Calder that December that stood for more than a dozen years. He concluded his racing career with 13 wins from 38 starts and earnings of $368,175.
Currently, Bishop has four horses in training. He retained a small share in this year’s Grade 3 Kitten’s Joy Stakes winner Chess’s Dream after selling a majority interest to Michael Dubb, Steven Bouchey and Bethlehem Stables, and is looking forward to the debuts of a couple of 2-year-olds. He also has four broodmares.
Bishop wants to see the industry that has provided him so much enjoyment thrive. But he is concerned about its future.
“The purse money is not as competitive as it used to be,” Bishop said. “Oaklawn’s purses are $100,000 and up, even for maiden special weight races; New York’s purses are up there. In Florida, we are helped by the weather – a lot of people still want to be here for the wonderful weather, but that only counts for so much. South Florida is prime real estate territory, and it has to be worth it to the owners to race, or the land will be redeveloped, like we see happening at Arlington Park, Hollywood Park, Calder. It’s troubling.”
As the Florida HBPA’s first vice president, he is working on initiatives to address racing’s issues.
“I’ve been on the legislative committee for a while, and I think that’s where I’ve been most helpful,” Bishop said. “I’ve gone to Tallahassee with the lobbyists and stakeholders, to help get our message into the equation. Our president, Stephen Screnci, has been negotiating on new revenue for our purses, that’s our best bet right now. And we have improvements planned for Palm Meadows, with new barns and dorms. That all helps.”
Creating a stronger year-round racing product is also a priority.
“If the horses aren’t staying here during the summer because of the purses and the high cost of maintaining a horse in south Florida, that’s a problem,” Bishop said. “During the summer, we see a lot of low-level claiming races; the horses bought for $100,000 or $200,000 have nowhere to run down here. We need to enhance racing in the summer to keep more horses down here.”
The work never ends. In addition to his commitment to the Florida HBPA, Bishop has also served on the Florida Consumer Council and was recently appointed to the Florida Horse Park in Ocala. Where does he find the energy?
“When you do something that really interests you, it doesn’t feel like work,” he said.
There are only so many hours in a day, but Bishop still finds time to relax.
“I love to go up to Ocala to see the horses, when I can find the time,” he said. “I love to see the horses, to name the babies. And family time is the most valuable – to just be in the backyard, go for a swim in the pool with friends and family. That’s the most important thing to me.”