“Winningest” Jockeys of Assiniboia Downs

Jun 14, 2024 | ASD History

by Track Historian Bob Gates

Let’s go for a walk and retrace the steps of jockeys that the newspaper scribes once called the “winningest” riders in the history of Assiniboia Downs.

“Winningest” is an awkward term and not one you hear much anymore.  So let’s go with the phrase All-Time Leading Jockeys (by wins). In an effort to address the repetitive nature of our story, all jockey wins are for those registered at Assiniboia Downs and the phrase All-Time Leading Jockey or ATLJ refers only to the Downs.

The first leg of our journey is a short one. In 1958 Hugo Dittfach won the riding title in the Downs inaugural season. Being the first rider to win the jockey title, Hugo set the benchmark for those who followed.

“Hustlin’” Hugo’s 55 wins in the 1958 season made him the first All-Time Leading Jockey. However, the larger tracks in the east were far too tempting, so Hugo headed to Ontario never to return to the Downs for anything other than the odd race where he would ride a “shipper.”

Who knew?  Hugo Dittfach would go on to fame and glory as a rider of thoroughbreds for more than 30 years and ride a total of 4,000 winners (all tracks) before retiring.

Spangled Jimmy ASD Handicap 1958. Hugo Dittfach up.

Statistical record-keeping in the late 1950s and early 1960s was sketchy. With Dittfach not around to defend his crown, the door was wide open for another rider to take over as the ATLJ.

Enter local boy, Tommy Stadnyk who won the Downs riding title in 1959, 1960, and 1961. Tom finished second in the standings in 1962 and third in 1963, before moving west to spend the balance of his career riding primarily in Alberta.

We can’t be entirely sure when Tommy passed Hugo’s 55-win mark, but pass it he did! By the end of 1962 Tom had notched 207 wins and held the crown as the ATLJ.

Who knew?  On June 23, 1961, Tommy Stadnyk became the first jockey in Downs history to ride five winners (Alta Pilot, Winna Peg, Chaps, Bushed, and Midland Empire) on a single card.

Bushed, June 23, 1961, one of five on the day for Tommy Stadnyk.

When the 1964 racing season was done Tommy had company atop the ATLJ board.  Both he and Maple Creek, Saskatchewan’s Dick Armstrong were tied with 246 trips to the charmed circle, even though Tom never rode at the Downs in 1964.

On July 2, 1965, Dick took sole possession of the crown when he scored win #247 aboard Khal’s Charm. He rode his last winner at the Downs on Speedy Wheeler on August 18, 1969, to bring his win total to 478. At the end of the 1969 season, Dick moved east and rode at tracks in Ontario. Once again, a jockey’s departure cleared the way for another rider to claim the crown.

Late in the 1970 season Humbolt, Minnesota native Bobby Stewart surpassed Dick’s 478 wins to take over the ATLJ title.  Bobby closed out the 1970 campaign with 486 wins.

Who knew?  On June 16, 1971, Bobby Stewart became the first Downs rider to notch six wins ( Stout Me, Brozle, Jumble Rhythm, Toy Stand, Willa Gray and Sparrowhawk) on a single card. 

Toy Stand, June 16, 1971 – NTR, one of six on the night for Bobby Stewart.

In the years that followed Bobby added 238 more victories and finished his Downs riding career with 724 wins. In the end, the wear and tear on Bob’s back became too much for him to bear. He was only 31 years old! Bob’s resume included the distinction of being the first rider at the Downs to reach the 500, 600 and 700 win-plateau.

Who knew?  In eleven seasons from 1962 to 1972 Dick Armstrong (1962, 64, 65 and 67) and Bobby Stewart (1966, 68, 69, 70, 71 and 72) won the leading rider title 10 times.

Speedy Wheeler last win at the Downs for Dickie Armstrong, August 18, 1969.

1983 Manitoba Derby. Gone to Royalty. Irwin Driedger’s last winner at the Downs.

Bobby’s 724 wins stood the test of time until 1981 when Jimmy Anderson, Ken Hendricks and Irwin Driedger re-wrote the record books.

On June 15, 1981, Jimmy rode Tilt Quiz to victory, it was his 725th win.  After win #725 Jim added one more win to bring his total to 726.  However, Jim’s claim to the crown was short – June 15, 1981 to July 8, 1981.

Who knew?  Jimmy rode quality, not quantity, consistently finishing high on the jockey leader board, but he never won a single-season leading rider title.

On July 8, 1981 Ken Hendricks booted home his 727th winner on Mr. Mar J Mar.  Ken would bring his total wins to 751 by September 9, 1981, before fellow rider Irwin Driedger would register his 752nd  winner passing Ken to “steal” crown.

From September 9, 1981 to the end of the 1982 season Irwin piled up the wins.  Yes, Irwin left us as well to ride down east following the 1982 season.  Irwin rode on Downs Derby day in 1983 and added two more wins bringing his total wins to 969.

Who knew?  In 1981 Irwin rode a record-setting 214 wins. 

Peaceful Miss. June 14, 1969. Ken Hendricks’ first win at ASD.

Irwin held the ATLJ title until June 3, 1988. On that day Ken Hendricks launched another assault on the ATLJ crown. Ken clawed his way back to the top when he recorded his 970th victory aboard We’re Not Sure.  The man they called “Hank” would go on to record an impressive 1,685 wins before hanging up his tack early in the 2008 season.

Who knew? In 1975 Ken Hendricks became the first jockey in Downs history to ride more than 100 winners in a single season. He finished the year with 111 trips to the winner’s circle.

Our journey has come to an end. How about a final tip of the hat to Hank and his stellar 1,685 wins, making him the Downs All-Time Leading Jockey.

Second place? Thing is, there is no active rider that is even remotely close. The last “Downs-Only” stats reveal that there are no riders in the top 20 that are still riding. Conservatively speaking, this leaves Hank more than 1,200 wins ahead of his closest active rival.

It is said that records are made to be broken…

But not this one!