Tall Tales of the Track: Bug Boys Get It Done for Father & Son

Apprentice jockeys often carry the moniker of ‘bug boy’ (or girl) because of the asterisk next to their names in a racetrack program. The ‘bug’ tells race fans that this horse gets the weight break new riders receive, a benefit meant to give them equal footing with their more experienced peers. Because they are new to the game, they rarely get opportunities to ride in the big races, but when they do, a spot in the history books awaits.

Ira Hanford and Bill Boland share a unique connection: not only were these two riders ‘bug boys’ when they won the Kentucky Derby, but their mounts were sire and son, making these winners singular in the annals of the history of the Run for the Roses.

Bold Venture 

Morton and Charles Schwartz were brothers in business and brothers in racing. While Charles is best known for owning 1926 Grand National victor Jack Horner, Morton had more success on the flat, with his filly Enfilade, who won the Beldame in 1917 and the Kenner in 1918, among her career stakes wins. Schwartz bred his own horses, and, in 1932, decided to pair his mare Possible with St. Germans, an English stakes winner standing at Helen Hay Whitney’s Greentree Farm near Lexington. On March 4, 1933, Possible foaled a plain bay colt that Schwartz would name Bold Venture. 

By 1935, Schwartz was ready to disperse his breeding and racing stock and get out of the sport after more than a decade. Possible went through the ring with her 1935 foal, a colt by Clock Tower, and sold for $3,000. Bold Venture also went through the ring, his quality such that Schwartz anticipated he might bring $20,000, but when the bidding went no higher than $6,500, Schwartz stepped in and tried to pull the colt from the sale. E.J. Tranter of Fasig-Tipton refused, and the businessman had to convince a friend to bid on Bold Venture on his behalf. Schwartz bought the colt back for $7,100. He would win that back in spades. 

Under the tutelage of trainer Max Hirsch, the future Hall of Famer who had already won a Belmont Stakes with Vito in 1928, Bold Venture started his career in a five-furlong test over the Widener course, a seven-furlong straight course cut through Belmont Park’s one-mile training track and its 1 1/2-mile oval. He finished second and then broke his maiden in another five-furlong test at Aqueduct. But when Bold Venture stepped up to stakes company in the Arlington Futurity, he acted up in the gate, throwing rider Tommy Malley and bolting down the track for nearly a mile. By the time he was corralled and reloaded, the St. Germans colt had run his race and finished last. 

A shift to Saratoga brought him more chances at success. He won two of four starts there, beating Belair Stable’s Granville and then a little-known horse named Seabiscuit in another race. Bold Venture rounded out his two-year-old season with a ninth-place finish in the Hopeful Stakes; Hirsch then opted to give the colt a break until the following April, when Schwartz’s colt returned to the races in a one-mile-and-70-yard test at Jamaica. The colt was then shipped to Louisville and Churchill Downs for the 62nd Kentucky Derby. 

Apprentice Ira Hanford had ridden Bold Venture at Jamaica, his first ride on the colt, and Hirsch wanted the rider back on the colt for the Derby. Still, he was not first call on Hanford’s contract: Mary Hirsch, the trainer’s daughter and the first woman licensed as a trainer in the United States, was technically the 18-year-old’s boss. She permitted Hanford to ride Bold Venture in the Derby while she stayed back in New York with her father’s horses. The rest is Run for the Roses history. 

Breaking from the sixth stall of the doorless Bahr gate, horses went crashing into each other "like a bowling ball hitting the pins,” as Hanford described it years later. The melee of horses crashing into each other, Bold Venture getting hit from both sides, caused rival Granville to lose his rider, Jimmy Stout. But Hanford somehow managed to escape the incident and went on to win by a head, just outlasting the favored Brevity. With that, Ira Hanford became the first apprentice jockey to win the Kentucky Derby. 

Bold Venture would win the Preakness as well, but an injury during training for the Belmont Stakes ended the colt’s career after only 11 starts. King Ranch purchased the Derby winner and brought him to Texas to stand stud, where he sired Triple Crown winner Assault and another classic winner in a colt named Middleground.

Middleground 

Verguenza was not a great racehorse for her breeder, King Ranch – she won only one of her five starts and earned a grand total of $775 – but her pedigree made her a valuable part of their broodmare band. Her dam, Blushing Sister, was a daughter of 1926 Kentucky Derby winner Bubbling Over, and so after a pairing with dual classic winner Bold Venture, her 1947 foal, a chestnut colt with two white socks and a blazed face, had Derby potential written all over him. 

As a two-year-old, Verguenza’s colt, named Middleground because he was foaled between two colts who were supposed to be good ones, showed his quality from the start. He won his debut, a 4 1/2-furlong maiden race down the Widener chute at Belmont Park, with King Ranch’s apprentice Bill Boland in the saddle. The colt raced four more times that season, winning three, including the Hopeful Stakes at Saratoga, until Max Hirsch decided to put Middleground on the shelf until the following year, owing to osselets, bony growths in his fetlock (or ankle) joints. 

He opened his three-year-old season with four straight second-place finishes, including the Wood Memorial and Derby Trial. Boland was back in the saddle for all four after Dave Gorman, King Ranch’s first-call rider, had ridden Middleground for all but his first start at two. He and stablemate On the Mark went postward for the 76th Kentucky Derby. Boland still had his bug at this point, having won his first race the year before and his first stakes a week earlier. The pair broke from post 14, the outermost post, and broke quickly enough to settle into fifth behind first Oil Capitol and then Your Host. 

Boland prompted Middleground to move boldly on the final turn as they passed Your Host to take the lead entering the stretch. He was able to hold off a surging Hill Prince in the final furlong to win by 1 1/4 lengths. Boland, who had won the Kentucky Oaks on Ari’s Mona the day before, became the second apprentice to win the Kentucky Derby. The first, of course, was Ira Hanford on Bold Venture, Middleground’s sire, 14 years earlier. 

Middleground would finish second to Hill Prince in the Preakness before turning the tables on his rival in the Belmont Stakes, easily notching another classic win while Hill Prince faded to seventh. He would retire later that season after fracturing a bone in the Jerome Handicap. Boland would go on to a Hall of Fame career in the saddle and remains the second and most recent jockey to win the Derby as an apprentice, his connection with Ira Hanford forever sealed thanks to sire and son.