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After those two disappointing races, Jones put in a call for Arcaro, who had won the 1938 Kentucky Derby for him aboard Lawrin. Arcaro wasn't particularly eager to ride the moody Whirlaway, and besides, he was under contract to Greentree Farm.
"I had seen too many good riders that couldn't handle him," Arcaro says. "I didn't know why they thought I could. They were having a lot of trouble with him. He would bolt."
Mrs. Joan Payson, the daughter of Greentree's owner, interceded and asked Arcaro to ride the Calumet horse.
"But I don't want to ride him," Arcaro answered.
"Well, you're doing me a favor," said Mrs. Payson. "And I owe Mrs. Wright a favor."
Reluctantly, Arcaro agreed.
Jones told the jockey: "I know you've heard so many stories about him, but you know I wouldn't send for you if I didn't think that I could correct it. This is the fastest horse in America, and with you riding him, we'll win the Derby."
Having Arcaro ride Whirlaway was only one of the changes Jones made. He also followed his son's suggestion to equip Whirlaway with a one-eyed blinker, which had a cup partly covering the right eye so as to make Whirlaway afraid to run to the outside. With Arcaro in the saddle, Whirlaway wore the one-eyed blinker in a workout on Derby eve as the fearless Jones positioned himself on a pony five or six feet out from the inner rail at the head of the Churchill Downs homestretch. The idea was for Whirlaway to hum around the corner and then hug the rail as he charged between the fence and the pony on which Jones was seated.
"I just said to myself, 'If the old man is game enough to stand right there, I guess I'm game enough to run him down,' " Arcaro recalls. " Ben Jones never moved a muscle, and Whirlaway slipped through the narrow opening as pretty as you please. I'll tell you, he was flying, too. If he had ever hit Ben Jones, neither one of us would have been around to talk about it."
With the lesson learned and Arcaro now sharing Jones's confidence, jockey and horse were ready. Whirlaway went off as the Derby's betting choice, albeit at a tepid 2.90-1. This time the bettors were not disappointed.