Starting at the bottom and climbing to success at the highest levels is no small feat, but for e Five Racing Thoroughbreds and Fifth Avenue Bloodstock’s Bob Edwards, it seemed the natural plan. The 54-year-old, who resides in Boca Raton, Fla., and Saratoga Springs, N.Y., with his wife, Kristine, put his proven pharmaceutical track record to work eight years ago when he got into the Thoroughbred industry, seeing the winner’s circle often.

This past weekend at Saratoga Race Course, Edwards saw his homebred Lope de Vega colt Carl Spackler cross the wire first with son-in-law Tyler Gaffalione in the tack for the one-mile National Museum of Racing Hall of Fame Stakes. In this interview with BloodHorse’s Lauren Gash, Edwards discusses his early success in racing, his relationships in the industry, and his Saratoga win with Carl Spackler, who is named after the groundskeeper in the 1980 film comedy “Caddyshack” played by Bill Murray.

BloodHorse: How did you get into horse racing in 2015?

Bob Edwards: My wife, Kristine, is from Saratoga, and we met in college in upstate New York. After serving as an MP in the U.S. Army Reserve, I moved to Florida to take a job with a drug company, and that’s where we started our family (daughters Cassidy and Delaney and son Riley). We would travel to Saratoga for a few weeks in the summer for vacation and to see family every year. Back in 2015, I had a business partner who moved to Fifth Avenue (which features the Oklahoma Training Track in its backyard), Steve Weston from Parkland Thoroughbreds, and he invited me to bring my daughter Cassidy to see the backside and let her check out the horses. My daughter had been riding horses forever.

We went and walked around the backside, which I hadn’t seen before. It was really cool, and (we) rolled right out to the Fasig-Tipton New York auction. He introduced me to Niall Brennan and Mike Ryan, who bought me my first round of horses.

Bob Edwards (Coady Photography)

BloodHorse: Your first year buying horses, you picked up New Money Honey and Zindaya at the sales; they turned out to be very special. What was your plan in the beginning when you started buying?

Edwards: It all started with no plan! After meeting Mike at the sale, we walked around for endless hours – he had no idea who we were, but he took his time explaining conformation, what he was looking for in a horse, how it all worked, and the whole deal. After I left, about three or four hours later, I called Mike and said, get me a horse. We wanted a horse for the next year, thinking if we got one horse, we would be running at Saratoga, and it would be a lot of fun for the family. That same day I was heading to a wedding; I dipped out to take a call from Mike when we started the bidding process.

After telling my family we got a horse, my wife said now we have to get a house (in Saratoga). Back at home, I started looking at horse racing stats, which aren’t spectacular for owning one horse. From there, I started going through pedigrees and learning everything I could about horse racing in 30 days to be prepped for the Keeneland September auction. We found New Money Honey at the September Sale; she was part of the first batch of horses.

New Money Honey, by Medaglia d’Oro, was purchased as a yearling by Mike Ryan for $450,000 during the 2015 Keeneland September Sale and won the Breeders’ Cup Juvenile Fillies Turf a little over a year later.

Zindaya, by More Than Ready, was purchased for $550,000 as a 4-year-old by Mike Ryan during the 2015 Keeneland November Breeding Stock Sale and won two stakes races in 2016, including the Grade 2 Goldikova Stakes.

BloodHorse: You saw early success with Breeders’ Cup winners New Money Honey (2015), Rushing Fall (2017), and Good Magic (2017) within the first two years you were racing. When did it all sink in that you had hit the big time?

Edwards: Knowing that the yearlings may not run at Saratoga the following summer, we purchased Zindaya as a racing/broodmare prospect at the Keeneland November Sale. She was broke at Vinery Stud, which is now Stonestreet Farm. I had met the Stonestreet folks when I sent them horses; they were familiar with Zindaya, which gave us confidence in the purchase. I spoke to Chad (Brown), and he confirmed he would take the horse.

Rewind to Keeneland September of 2015, where we purchased New Money Honey. She went out at 2 and won the Miss Grillo Stakes at Belmont Park and then the Breeders’ Cup Juvenile Fillies Turf at Santa Anita Park; at the time, we had no idea what it all meant. I had no idea what the Breeders’ Cup was; we went and were excited. We had won a race, and it looked like any other race; everyone was dressed up and having a good time. It wasn’t until they said they wanted to take our picture, people were standing in front of us, we turned around, and there were dozens of photographers on the track wanting to take our picture. That’s when it sunk in how impressive and important the Breeders’ Cup truly is.

The next day Zindaya won the Goldikova Stakes. For us, it was a perfect weekend. After the Breeders’ Cup, we started buying well-bred mares to breed, knowing that even if some of the yearlings didn’t run, we could breed them down the line.

It was right after that when we purchased Rushing Fall at the Fasig-Tipton Saratoga Sale in 2016, and I partnered with Stonestreet on Good Magic, and we were back in the Breeders’ Cup. We saw the winner’s circle twice that year, which was really special.

Mike Ryan purchased Rushing Fall, by More Than Ready, for $320,000 at the 2016 Fasig-Tipton Saratoga Selected Yearlings Sale. She won 11 of 15 starts, including six Grade 1 stakes, and sold for $5.5 million as a broodmare prospect in 2020.

A son of Curlin, Good Magic was purchased during the 2016 Keeneland September Sale for $1 million. He won the Breeders’ Cup Juvenile in 2017, finished second in the 2018 Kentucky Derby, earned over $2.94 million, and has become a successful young sire whose progeny include 2023 Kentucky Derby Presented by Woodford Reserve winner Mage.

Campaigning Good Magic, being second in the Kentucky Derby and winning the Haskell Invitational Stakes in 2018, along with him having a phenomenal first crop of runners, is great for our program.

Edwards (left), Good Magic, and connections at Keeneland. (Eclipse Sportswire)

BloodHorse: This past weekend, Aug. 11 at Saratoga, you had a big win with your homebred Carl Spackler capturing the National Museum of Racing Hall of Fame with son-in-law Gaffalione in the tack, along with breeding two other contenders in Bat Flip and General Jim. What did Friday’s victory mean to you and your family?

Edwards: I would have loved to see them go one, two, three, but unfortunately, it didn’t play out that way. My son-in-law, Tyler, was on the horse and that was the first graded stake he’s won for us as a family. This weekend was exceptional, obviously with the win, but we have 25-plus mares, and we are in the breeding business. Selling horses helps pay for the racing, and to have the other two that we sold in the race was a great testament to the quality of horses we are breeding.

BloodHorse: What is the business plan between e Five Racing and Fifth Avenue Bloodstock? How do you decide what to sell?

Edwards: I have an unbelievable Into Mischief colt out of New Money Honey. There was no shot he was coming to the Saratoga Sale (this year), even though he was possibly the best-looking of my yearlings. My family wouldn’t allow that to happen; the mare is a family favorite. She had a tough foaling the first time out and lost a foal, so there was no way this one wouldn’t remain in our stable and run for us.

Zindaya is back in foal to Uncle Mo for 2023. Her yearling Lope de Vega colt, a full sibling to Carl Spackler, will be offered at the Tattersalls October Yearling Sale in England this fall.

It starts there, then I have mares that put lovely babies out that we think offer an opportunity to spread out a bit. Run at different tracks with other trainers, allowing the mare to get some black-type on her breeding side, making the mare more valuable. I sometimes breed commercially and sometimes to race, trying different crosses to improve my breeding program.

BloodHorse: Both bloodstock agent Mike Ryan and trainer Chad Brown have been essential to your success. How does having them on your team give you a confident edge?

Edwards: Chad is a good friend. He trains my horses; we spend a lot of time together when he’s in Florida. He lives seven miles from my house, so we do dinner frequently. He’s a great sounding board for my entire operation. Some of my horses go to other trainers because maybe they aren’t for New York or don’t fit his program. Wesley Ward gets some stuff I want to go to Royal Ascot with; that’s his model.

I look for different trainers. You don’t want to give the same style of horse to the same trainer because you want to split them up a bit and maybe not run them against each other. Working in that mindset has been a huge part of my success. Having three Breeders’ Cup wins, second in the Derby, and a Haskell plus another Grade 3 win here at Saratoga is always memorable.

Mike has picked the majority of my horses out. Sometimes, if he’s not at a French sale or Tattersalls Book 2 or OBS later in the year, I will have a trainer pick out a horse, but for the most part, he is my main guy.

BloodHorse: You have raced alone as e Five Racing, but also a bunch in partnerships. Why?

Edwards: It’s a lot of fun. We have horses with Madaket Stables’ Sol Kumin, Jim Carey, and Jim Pallotta; they are three great guys to deal with. We have some property together in Saratoga; our families get together and have a lot of fun. Typically, we buy colts unless it’s something from Europe. It’s feast or famine with colts, so it’s OK to spread the wealth. Outside of Carl Spackler, I don’t think I have owned a colt alone in a long time.

Occasionally, you breed a horse and somebody wants to stay in for a leg, and I like to do that. Sometimes if you breed and raise it, it’s hard to sell a horse because you fall in love, so staying in isn’t a bad option.