The biggest win of Little Bold John's career came at Gulfstream Park in the 1987 Grade 2 Donn Handicap in which he defeated Skip Trial, Wise Times and the defending Eclipse Award-winning Horse of the Year Lady’s Secret.
The Donn Handicap-G2 was one of Little Bold John's eight stakes wins in 1987, a season in which he earned $599,041 from 18 starts, all in stakes.
Making his Maryland Million debut in 1987, Little Bold John won the richest race on the card, the Budweiser Maryland Million Classic, by four lengths. He finished third in the next two runnings of the race.
The richest race on the Pimlico summer calendar in 1988 was the Grade 3 Baltimore Budweiser Breeders' Cup Handicap, which Little Bold John, carrying top weight of 124 pounds, won by a nose over Dogwood Stable's Ron Stevens (right).
Little Bold John captured back-to-back runnings of Pimlico's Grade 3 Riggs Handicap, the second coming in 1988 while carrying top weight and defeating Along Came Jones. It was his third stakes win in five weeks.
Little Bold John turned the tables on Master Speaker in the 1989 Polynesian Handicap. The two met three weeks earlier in the Maryland Million Classic, which Master Speaker won by a length while in receipt of six pounds with Little Bold John running third, a neck behind Due North.
A mad dash to the wire in the the $200,000 General George Stakes, one of Little Bold John's rare appearances in a race at a distance under one mile. He completed the seven furlongs in 1:22 4/5 while defeating Oraibi (right) and Finder's Choice (second right).
A mad dash to the wire in the the $200,000 General George Stakes, one of Little Bold John's rare appearances in a race at a distance under one mile. He completed the seven furlongs in 1:22 4/5 while defeating Oraibi (right) and Finder's Choice (second right).
The durable bay son of John Alden made at least one start each month from January through September in 1987. His first start in August resulted in a victory over Entitled To in the Marylander Stakes at Pimlico.
Maryland through and through, millionaire Little Bold John's career lasted nine years through 105 starts, 38 wins, and an all-time record 25 stakes wins.

The “blue collar millionaire,” Little Bold John is the second-leading Maryland-bred by number of stakes wins on the flat with 25. The most dominant Maryland-bred handicap horse of the latter half of the 1980s, he earned divisional titles in 1988 and 1989, and when retired in 1992 at age 10, he was the third-richest Maryland-bred in history with earnings of $1,956,405.

Little Bold John represented decades of breeding by Hal C.B. Clagett. A son of John Alden out of the Bold Ambition mare Little Bold Sphinx, he was initially raced by Clagett, who sold him privately at the end of his 2-year-old season to first-time owner John E. Owens III. Trained by John J. Robb for his entire 105-start career, Little Bold John won 38 races, placed in 30 more, and for five consecutive years (ages 3 to 7), made 11 or more starts a season.

Little Bold John crossed the wire first in the Tri-State Futurity at Charles Town in November 1984, but was disqualified to fourth, which is what prompted Clagett to sell him. “My stable wasn’t doing too well, and to balance the books I needed cash,” remembered Clagett in 2003. “Little Bold John was my most valuable horse, so when Jack Owens offered me $30,000 I took it.”

Little Bold John didn’t get his first official stakes win until the Edward L Blake Memorial Handicap at Charles Town the next May. He went on to win two more that year, won three the next, and had his most productive season in 1987. His eight stakes wins from 18 starts that year included the Grade 2 Donn Handicap over a field that included the previous year’s Eclipse Award-winning Horse of the Year Lady’s Secret. He also won the first of three consecutive Jennings Handicaps, as well as the Grade 3 Riggs Handicap while amassing $599,041 in 1987.

Little Bold John became a millionaire in 1988, coming back after a six-month layoff when he pulled a high suspensory ligament in his left hock while winning the Maryland Million Classic the previous fall. He won seven more stakes while making at least one start a month from March through December, and had a five race win streak which included the Jennings and Never Bend Handicaps.

At age 7 in 1989, Little Bold John won three stakes in a row early in the year - the General George Stakes at seven furlongs, and the Jennings and John B. Campbell Handicap-G3 at a mile and an eighth, the latter two while conceding significant weight to the runner-up. The final stakes win of his career came in that fall’s Polynesian Handicap, in which he defeated Master Speaker.

Little Bold John went out a winner, taking a $50,000 claimer by a nose in October 1992. He initially didn’t enjoy a life of retirement, and Robb used him as a stable pony at Bowie for about a year, until a filly bit the old gelding and he kicked her, recalled Clagett. Clagett offered to take Little Bold John back to retire to Weston, where he was foaled and raised.

“Robb replied that he wouldn’t give the horse to me but would agree to a sale,” said Clagett, who agreed, and paid Robb one dollar to complete the sale. Little Bold John lived out his retirement at the farm in Upper Marlboro, Md., until his death from colic on January 21, 2003.

Little Bold John's Race Record











2 1984 7 1   1   2   $9,950
3 1985 19 6 (3) 5 (2) 1 (1) $172,615
4 1986 11 5 (3) 2 (2) 0   $182,486
5 1987 18 8 (8) 3 (3) 3 (3) $599,041
6 1988 16 8 (7) 1 (1) 3 (3) $505,724
7 1989 13 4 (4) 1   2 (2) $382,451
8 1990 3 0   0   0   $0
9 1991 9 3   1 (1) 2   $57,074
10 1992 9 3   2   1   $47,065
  Totals 105 38 (25) 16 (9) 14 (9) $1,956,406


In January 2013 the Maryland Horse Breeders Association (MHBA) and the Maryland Racing Media Association (MRMA) began collaborating on plans for a hall of fame to illuminate the accomplishments of Maryland-bred Thoroughbreds.