Though he grew up loving horses, Jim Ryan did not get into the racing business until he had cultivated a fortune through his home-building businesses, Ryan Homes and Ryland Homes. The Pittsburgh native took Ryland public in 1971, which netted him enough cash to start investing in horses. Ryan listened to his brother’s advice about making his mistakes with inexpensive horses and started small with a stable at Charles Town in West Virginia.

His ambitions, though, were big.

“I’d like to take a shot at winning the Triple Crown races,” he told his first trainer Bobby Hilton.

To get there, he bought Ryehill Farm outside of Mt. Airy, Maryland, and started investing in bloodstock. He bought a mare named Smartaire for $36,000, who produced Quadratic, a graded stakes winner and regional sire; Smart Angle, champion two-year-old filly of 1979; and multiple graded stakes winner Smarten. Ryan bought another mare Turn to North and her weanling filly Cold Hearted sight unseen based on a recommendation from a bloodstock agent. Cold Hearted would later become a stakes winner at Hialeah and then retired to broodmare duty at Ryehill.

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Ryan paired Cold Hearted with Cannonade, the 1974 Kentucky Derby winner who survived the cavalry charge of the 23-horse field to take the 100^th edition of the Run for the Roses by 2¼ lengths. On March 16, 1980, Cold Hearted foaled a dark bay colt with a smudge of white on his forehead, whom Ryan would name Caveat. Together with partners Robert Kirkham and August Belmont IV, the Ryans decided to send the colt to Cannonade’s trainer, the Hall of Famer Woody Stephens.

From Inconsistent to Improved

At two, Caveat’s late-running style made getting that maiden victory challenging. He broke his maiden in his fourth start, a maiden special weight in early August at Saratoga. Eight weeks later, he won the Prince John Stakes at Belmont Park and then finished second or third in five stakes to round out his 1982 season. Caveat finished with three wins in eleven starts at two, with Ryan and partners setting their sights on the Triple Crown classics in 1983.

One of his most notable starts as a juvenile came in the November 27 Maryland Juvenile Championship. He finished third that day, bested by future multiple graded stakes winner Dixieland Band and the following year’s Preakness winner, Deputed Testamony.

In his first start at three, Caveat finished second to My Mac in the Tropical Park Derby at Calder, a promising start to the season, but three consecutive out-of-the-money finishes in races like the Florida Derby and the Fountain of Youth left Stephens scratching his head. By then Caveat looked less promising than his stablemate Chumming.

At Oaklawn, though, the son of Cannonade showed his connections that he deserved to be in the conversation for that year’s Kentucky Derby. After winning an allowance, Caveat finished a strong second behind Sunny’s Halo in the Arkansas Derby, which earned him a spot in the starting gate for the Kentucky Derby.

A week before the Run for the Roses, Stephens started the colt in the one-mile Derby Trial, and under new jockey Laffit Pincay, Jr., Caveat eked out the win by a head. That led to a late running third in the Kentucky Derby, overcoming a wide trip to improve from 17^th to finish less than three lengths behind Sunny’s Halo.

“We probably should have won the Derby,” Woody Stephens said later. “He ran a big race. He was probably the best.”

The trainer opted to rest the Maryland-bred, skipping the Preakness Stakes to try the Belmont Stakes. Deputed Testamony won the Preakness with ease and aimed for the last Triple Crown classic as well, joining Dixieland Band and Caveat in the 115^th running of the race named after partner August Belmont IV’s great-grandfather. Under Pincay, Caveat started from post position seven, facing fourteen others in what is the largest Belmont field to this day.

It was time to see if Jim Ryan could fulfill his goal of winning a Triple Crown classic with his son of a Derby winner.

From Start to Finish

Caveat started slowly out of the gate, sitting 11^th after the first quarter. Pincay bided his time on the backstretch of the 1½-mile classic, waiting until the mile mark to move the colt up to eighth. On the far turn, the jockey spotted a fast-closing hole on the inside and daringly sent the colt through it, bouncing off a fading Au Point as they rounded into the stretch.

In the Belmont straight, Caveat pushed through on the rail and took the lead inside the final quarter. Under Pincay’s urging, he drew away to a 3½-length victory over Slew o’ Gold and Barberstown. Fellow Marylanders Deputed Testamony and Dixieland Band finished sixth and fourteenth, respectively.

For the partnership of Ryan, Kirkham, and Belmont, the victory was the culmination of years of breeding, owning, and hoping for the right horse to take home a win on a day like that, and Belmont became the first of his family to win the namesake race since 1917. For trainer Woody Stephens, the son of Cannonade was the second in what became a five-year winning streak in the Belmont Stakes, following his win the year before with Conquistador Cielo.

For Caveat, though, his win came at a cost: he injured a ligament in his knee making that move past Au Point on the far turn. The injury lingered and kept the colt from returning to training for the rest of the season.

[WATCH: Caveat wins the Belmont Stakes]

In mid-August, the partners opted to retire their Belmont Stakes winner and sent him to stud at famed Windfields Farm in Chesapeake City. Syndicated for $7 million, Caveat stood stud there until his death in 1995, siring 300 winners and 35 stakes winners from 424 foals. The best of his progeny included Cefis, named for trainer Woody Stephens; Timely Warning, Brooklyn Handicap winner; and Awad, whose multiple graded stakes wins included the Arlington Million, the Sword Dancer Invitational, and the Secretariat Stakes.

As for Woody Stephens, Caveat joined Conquistador Cielo, Swale, Crème Fraiche, and Danzig Connection as his record five consecutive winners of the Belmont Stakes. That feat alone merited his induction into the Hall of Fame – had he not already been inducted in 1976 – but his wins with Cannonade and Swale in the Kentucky Derby and Blue Man in the Preakness Stakes were just a few of the accomplishments that brought him the honor.

Jim Ryan continued racing and breeding into the late 1980s, but, as he grew more aware of the conditions on track backsides, he devoted more of his time and fortune to advocating for backstretch workers. He dispersed his stable in 1988 and used the proceeds to start the Ryan Family Foundation, which distributed grants for programs that benefitted underserved populations, including disabled and homeless persons.

Caveat concluded his career with six wins from 21 career outings. And on that day in June 1983, he carried Jim Ryan and his partners to the very top of the horseracing world.