Maggi Moss and Greg Tramontin

This was an unlikely partnership because Maggi Moss’ storied career as an owner was strictly a solo act (including being named national owner of the year by the Thoroughbred Owner and Breeders Association in 2007 after becoming the first woman to finish as the leading owner in the country since 1945). “I’m a real control freak,” Moss, an attorney in Des Moines, Iowa, said. “I don’t play with others. It’s my money. It’s my horses. I take in the good news, the bad news, the disappointments and everything in between. If something goes wrong, it’s on me. I’m a one-man band, and it worked well with me.”

Until February. Still suffering from the loss of her mother last December, Moss was flooded with offers to buy her undefeated three-year-old colt No Parole, who had won his first three starts for Louisiana-breds, a maiden race by 14 ¼ lengths, an allowance race by 13 ¼ lengths and the a $100,000 Premier Night Prince Stakes by 6 ½ for Tom Amoss, Moss’ long-time trainer. “I received several generous offers—very generous—over a million dollars,” she said. “I didn’t take partners, but most of those offers were by individuals who wanted 100 percent of the horse, and more importantly, wanted to take him away from Tom. I am fiercely loyal to Tom after 17 years. He had developed the horse. I bought him, but Tom developed him. He won those races—he and his crew. Taking the horse away from him didn’t seem right.”

That opened up a possibility: finding a partner who would take less than 50 percent and be happy to keep Amoss as trainer. Tom suggested Greg Tramontin. “I didn’t know who he was, but I trusted Tom. Tom said he would be a great partner,” Moss said. “The deal was really smooth. He’s wonderful. He’s smart. He is the perfect partner. Now we’ve partnered on another horse.”

Tramontin, the 2009 founder and CEO of GoAuto Insurance in Louisiana, had just reconnected to horse racing and was delighted to take a 49 percent interest in No Parole, who improved his career record to five-for-six with a powerful 3 ¾ length victory in the Gr1 Woody Stephens Stakes at Belmont Park June 20.

“I had called Tom in January to see if we can get anyone for the Kentucky Derby—a bucket item,” Tramontin said. “He said he has a fantastic horse, not just a fantastic Louisiana-bred. I didn’t know Maggi, but now we talk on the phone almost every day. She’s the best partner you could have. She’s been a fantastic partner. Tom put us together. Now, we’ve purchased another horse at the March Sale, Let It Be. We’re now 50-50 partners. I gained one percent.”

Joking aside, Tramontin, now 66, tipped off his future business acumen at the age of six. That’s when he won a competition at his Chicago Catholic school for selling the most doughnuts in his first-grade class. “The doughnut contest?” he asked. “I’m a competitive guy by nature. I was a cute little first grader. I went up and down every block in Chicago. I sold more than any kid in the whole school. They brought a truck to deliver those doughnuts. My mom didn’t know she had to deliver them. She got mad at me.” Tramontin received a wooden statue trophy of the Virgin Mary. “That’s still on my desk,” he said.

His business education was aided mightily by his grandmother around the same time. “She gave me three stocks,” he said. “I had to come home and look them up in the paper every day. The three stocks were Sears, Marquette Cement and El Paso National Gas. That wound up paying my tuition to LSU. That got me from Chicago to Baton Rouge.”

The son of a tool company worker, Tramontin grew up near Sportsman’s Park, but he didn’t get into horse racing until his close friend Bob Asaro bought a horse for $2,500 in 1989. That horse, Genuine Meaning, was named Louisiana-bred Two-Year-Old Champion and earned nearly $300,000. “Bob’s telling me, `This is easy,’” Tramontin said.

It’s not. Tramontin bought his first horse, Windcracker, who broke down in training and had to be euthanized. “Then Tom, who’s always been my trainer, calls me from England and said there’s a Louisiana horse, Artic Tracker, in a sale there,” Tramontin said. “He said he was Group placed in the 2,000 Guineas but caught the equine virus. He said, `This is a really nice horse. We’ll have to pay $40,000.’”

Tramontin said, “I’ll do it one more time, Tom.’”

They got the horse...for $80,000. Amoss told him not to worry because he found a partner for the horse in Texas. That partner reneged, so Amoss took a $10,000 share as did Bob Asaro. Artic Tracker was worth it, earning $241,795 from eight victories, nine seconds and 11 thirds from 47 starts.

In August 1994, Tramontin almost bought the horse of a lifetime, two-time Horse of the Year Cigar. “Artic Tracker had just won a stakes at Louisiana Downs,” he said. “I told Tom, `Let’s find another horse and try to get into the next level.’ He called and said, `I found one: a three-year-old in California.’ Tom said he’d been racing on turf, and that the horse is racing on the wrong surface. We made a bid for $175,000 on a Friday, and they said they’d consider it.”

Over the weekend, owner Allen Paulson decided not to sell his would-be star. “In October, he wins the first of 16 straight on dirt,” Tramontin said. “I watched him on TV and threw my sock at the TV.” By the end of Cigar’s run, Tramontin was out of socks.

Despite missing out on Cigar, Tramontin was enjoying racing, but he decided to get out when he entered the insurance business in 1995 after a successful five-year run with the Yellow Pages, beginning as a sales rep. “I didn’t want to get criticized for being in the horse business,” he said. “Insurance is a regulated industry. I took a hiatus from racing.”

He didn’t return for 23 years.

While Tramontin was out of the game, Moss, a three-time champion hunter/jumper, was flourishing. Horses have always been in her life. “It started when I was eight years old,” she said. “My dad was very adamant about learning about horses before he bought me show horses,” she said. “He had come from Chicago, and he loved horses.”

Moss joined the pony club, then got involved in hunters and jumpers. She won a national show jumping championship at Madison Square Garden.

“I came up with some of the greatest horsemen you’ll ever meet,” she said. “I rode competitively until I went to school at the University of Kentucky.”

She brought her horses to Lexington to keep competing, but found a whole new way of life in college and asked her father to pick up the horses and take them back home. “I had never had a social life,” she said. “I never had any life other than horses. I’d never left my mom and dad. I joined a sorority. You drink, you party, you meet boys. I had the time of my life. I had too good of a time—a way too good of a time. I did all the crazy things. I was in college. I got placed on probation the first semester.”

Eventually, Moss calmed down her college lifestyle, deciding to go to law school. “I got involved in law,” Moss said. “I got really serious. I worked in the Appalachian mountains with poor people. I switched from animals to people.”

She served as a public defender, then as a prosecutor and finally in a private practice. “I had some high-profile cases,” she said. Most were with personal injury, discrimination and victims’ rights.