The Winnipeg Free Press Trophy (Jason Halstead / Assiniboia Photo)
By Track Historian Bob Gates
On Tuesday, June 23, 2026, the Free Press Stakes celebrated its 66th running and our congratulations go out to the winning connections. The history of the race dates back to 1960 and while we now know it as a sprint championship for 3-year-olds and upward, that hasn’t always been the case.
In the early years, the race was known as the Free Press Handicap and was usually run on the final day of the meet. In addition, the race suited marathon specialists, as the winner had to run a route of ground, covering distances anywhere from 1½ to 2¼ miles.
This week you are being treated to an assortment of photos from the 1960s, 1970s, 1980s, 1990s, and the 2000s. Please enjoy our little trip through time as we remember some “oldies but goodies.”
Broad Zone August 16, 1961 (Assiniboia Downs Archives)
Broad Zone won the 1961 Winnipeg Free Press Handicap, going 2¼ miles. Our little hero was owned by the savvy veteran horseman, Wendell Holmes Mustard of Gladstone, father of our own lovable Doug Mustard. Broad Zone was your garden-variety, low-level claimer, but somewhere within the undersized gelding was a one-time competitive charge that when ignited, resulted in the greatest win of his life.
Free Press Trophy Presentation circa 1968 (Gerry Hart)
You have to love this picture! On the right is Eileen and A. E. “Bert” Blake being presented with the Free Press trophy. Sadly, we can’t identify the people on the left, but we do know the Blakes won the 1968 Free Press with Bold Fleet.
Rejected Judge August 11, 1974 (Gerry Hart)
On August 11, 1974, Ken “Hank” Hendricks piloted Rejected Judge to victory in the Free Press. The Clayton Gray-trained gelding won the race, while Hank won the leading rider title and Clayton won the leading trainer title for the 1974 season. Pictured above are Hank and Clayton receiving Gruen watches for their respective titles from Downs General Manager Bill Clubb on the last day of the meet in 1974.
Major Enterprise May 29, 1981 (Gerry Hart)
During his illustrious career at the Downs, Major Enterprise contested the Free Press on four occasions, chalking up a victory, a second and third-place finish. Here, the Major is seen winning the 1981 Free Press Allowance Stakes, narrowly defeating Northern Spike and Romeo Frank.
P C’s Bluff June 18, 1995 (Gerry Hart)
On June 18, 1995, P C’s Bluff proved he was one of the best to compete in the Free Press Handicap. From 1994 to 1997, Stan Ryan’s gelding went three for three, winning the event in 1994, 1995 and 1997. P C remains the only three-time winner of the Free Press.
Smoky Cinder June 17, 2001 (Gerry Hart)
Smoky Cinder was as tough a competitor as the Downs has known. He ran in the Free Press five times. In 1998 he finished second, in 1999 he won, in 2000 he finished fourth, in 2001 he registered his second victory and in 2002 he finished fourth. Pictured above Smoky is seen beating an always game Kalfaari in the 2001 edition of the Stakes.
Kalfaari June 23, 2002 (Gerry Hart)
To round out our photo blog of the Free Press Stakes, we have “The Peoples’ Horse,” Clint Willson’s Kalfaari. Above he is seen winning the 2002 Free Press. Kalfaari was one of those horses “who always showed up.” He put his heart and soul into every one of his outings on the track.
Kalfaari was one of the Downs’ all-time champions with a spirit that others could only dream about. The news of his passing in May 2004 stunned the local racing world, when he “collapsed and died during a morning gallop.” Who would have thought that a heart so strong would ever stop beating.
I hope you enjoyed our Free Press visual presentation. The race had many fine champions, and these were but a few…
Of those that left their hoofprints at Assiniboia Downs.