Matt J. Winn (1861-1949), the tailor who saved Churchill Downs from insolvency and built the Kentucky Derby into prominence, was the son of an Irish immigrant to Louisville, Kentucky.  The master marketer and promoter saw, in person, every Kentucky Derby from 1875 through 1949.

Winn wrote in his 1945 autobiography Down the Stretch:  The Story of Colonel Matt J. Winn:

“Late in the autumn of 1902, Charlie Price, former newspaper editor, and the secretary of Churchill Downs race track, dropped into my office, set down, and, without preliminary, bluntly asked me to buy Churchill Downs property.

‘Why should I do that?’ I encountered.

‘Because,’ replied Price, ‘if you don’t buy it, the track will have to close and there won’t be any more Kentucky Derbies.’

‘What’s the answer?’ requested Price…?’

‘I’m a merchant tailor—and a horse player,’ I told him.  ‘That satisfies me.  Find another customer.’

‘I can’t,’ said Price.  ‘I’ve been all over town trying to get a buyer.  No one wants it.  I’m trying you as the last resort.  Buy it and keep the Derby alive.  If you don’t, the Derby dies.’”

Winn thought over the entreaty and put together a group of wealthy locals to purchase Churchill Downs, which had never made a profit, for $40,000 ($1.1 million in 2017 dollars).

The tailor, horseplayer, and honorary Kentucky Colonel took over Churchill Downs and the Kentucky Derby in 1903, gave it increased legitimacy by convincing Harry Payne Whitney to run the filly Regret in the 1914 edition, and navigated perils like antigambling sentiment, two World Wars and a depression, until his death in 1949 at age 88.

After Winn’s turnaround of Churchill Downs, he became very successful in managing racetracks in the United States and Mexico.  Like most humans, Winn extrapolated the present into the future.  Consider, in 1945, his vision for horse racing before the days of simulcasting, huge television audiences, the Internet, and a vast array of entertainment options:

“As I look down the vista of the years ahead of us…I can see monster racetracks in operation; I can see crowds of 50,000 and 60,000 on normal days—100,000 crowds on the Saturdays and holiday; I can see gigantic parking places for the automobiles of the future; huge landing fields for the planes that will carry race patrons almost to the gates of the track.”

Winn the octogenarian would probably be amazed with what Churchill Downs has become today, with its size and expansion into gaming.  He would no doubt be surprised by simulcasting and the Internet and the change they wrought in horse racing, and the growth of the NFL and the NBA.

Put any of us into the future many decades after our death and the world would be foreign and difficult to comprehend.

The man who saved Churchill Downs and the Kentucky Derby was an innovator for his era.

Copyright © 2017 Horse Racing Business

The series on Kentucky Derby history began on February 20 and concludes on May 1, with articles appearing every Monday.