04/27/2007 12:00AM

History Challenge: Derby bloomed in his stewardship


By the beginning of the 20th century, the Kentucky Derby had become an obscure local event, often attracting only four or five starters. Its home, Churchill Downs, had not had one profitable year since in opened in 1875.

Then, in 1902, a local tailor with little experience in racing - Matt J. Winn - was persuaded to form a syndicate to buy the track for a reported $40,000. The first meeting under Winn made a small profit. When Winn died in 1949, just months after the 75th Diamond Jubilee Derby, the track had never suffered a losing year under his leadership.

A chubby, affable, cigar-smoking gentleman, Winn was a genius at promotion, and the Derby was his love. Renowned racing journalist Joe Palmer wrote:

"To men who have never seen a horse race and never will, the twin towers of Churchill Downs and the roaring lane to the finish of the Kentucky Derby have symbolized racing. That this is true was the work and the monument and, at the last, the only desire of Colonel Winn."

Test your knowledge of this 20th-century racing giant.

1. After his first season as part-owner of Churchill Downs, Matt Winn was asked to take over as general manager. He was in his early 40s, and this meant abandoning a successful tailoring business and taking a huge financial risk.

After these three consecutive runnings of the Derby, Winn said he knew he had made the correct decision. These three races combined to make the Kentucky Derby a national event and set it on its way to becoming America's most famous race. Name the winners of the three races.

2. Winn's first major crisis after taking over as general manager was an effort by the state of Kentucky to join most other states in banning betting on races - more specifically, banning bookmakers.

After moves by the governor and city hall in Louisville, it looked for a while like the 1908 season at Churchill Downs would have to be scrapped. Winn's lawyers dusted off an old state law and got a court to agree that the parimutuel form of wagering - unsuccessfully tried in the past - was legal. Bookmakers were out, machines were in.

How many parimutuel machines were in operation for the 1908 Kentucky Derby?

3. Winn's name is almost always associated with the Kentucky Derby and Churchill Downs. But he was involved with, managed, and/or was part-owner for years of racetracks as far south as Mexico City and as far north as New York, as well as all over the Midwest.

Winn's most challenging assignment was coddling the notorious Mexican outlaw Pancho Villa to keep open a racetrack that the Winn had built. Villa was persuaded by the charm and wit of Winn - and, of course, by being put on Winn's payroll. Name the racetrack.

4. As legend goes, Winn saw the first Kentucky Derby in 1875 from the infield on his father's grocery wagon when he was only 13. He never missed another until he died nearly 75 years later. This, combined with his involvement with many other tracks, enabled him to see all of the greats, from Hindoo to Citation.

In his 1945 autobiography, "Down the Stretch," Winn devotes a chapter to a horse who he called the greatest he ever saw. Name the horse.

5. Churchill Downs was always Winn's first love. But he owned part of, and/or managed, Empire City and Jamaica in New York, Laurel in Maryland, City Park and Fair Grounds in New Orleans, and Latonia, Douglas Park, and Lexington in Kentucky, among others. But it was a track in Illinois in which he always said he took the most pride. Name it.