Uneasy Victor

One Red Rose for the Green Kid Who Won the Kentucky Derby

Little Bill Boland was only 18 when he rode Middleground to victory in the 1950 Kentucky Derby. The only place he was comfortable was on the back of a horse.

05.03.14 9:45 AM ET

Who better to turn to for the Kentucky Derby than Red Smith, that elegant stylist widely considered our finest sports columnist. So please enjoy “One Red Rose: The Green Kid on Middleground Plucks a Derby Trophy,” which ran on May 6, 1950. It is featured in the comprehensive Smith compilation, American Pastimes: The Very Best of Red Smith, edited by Daniel Okrent and published by The Library of America. The column appears here with permission.

The bawling of the crowd still thundered up into the gray skies when the jockeys came striding through the alley from the track to the riders’ quarters beside the Churchill Downs paddock. The seventy-sixth Kentucky Derby was over, and the losers walked swiftly, as though in a hurry.

Little Bill Boland, the 18-year-old apprentice who never won a stakes race before last Saturday, never visited Churchill Downs before this week, and never saw a Derby before this afternoon, wasn’t with them. He was sitting on his horse, Middleground, in the big horseshoe of carnations growing in front of the tote board, fingering the blanket of roses they had hung over his lap while the King Ranch trainer, Max Hirsch, accepted congratulations, and the owner, Robert Kleberg, accepted $92,650 and a $5,000 gold cup.

In the second swiftest and perhaps the prettiest and most exciting of Derbies, Boland had brought Middleground around the rushing Mr. Trouble and the punctured California bubble, Your Host, to take command at the top of the stretch. He had run away from the powerful Hill Prince and swept under the wire the winner by a length and a quarter.

Now as the losers hustled away, Eddie Arcaro and Johnny Longden walked side by side. They’d been up on the two favorites—Longden on Your Host, which was 8 to 5, and Arcaro on Hill Prince, which was 5 to 2. Hill Prince had earned $10,000 in second money. Your Host had got there ninth, four lengths ahead of the bush-league rookie, Hallieboy, which made sordid company for a Hollywood immortal.

“I was lucky, too,” Arcaro was telling Longden. “I got the breaks.” He stepped along, lashing abstractedly at a boot with his whip.

“You never had any trouble anywhere?” Eddie was asked.

“Not anywhere,” he said. “The only horses I had to come around were the leaders. I was lapped on the winner at the quarter-pole, but he opened up two lengths on me.”

“You were coming hard in the last sixteenth.”

“I didn’t think I was catching him at the finish,” he said. “Did it look like it? Well, maybe Hill Prince was picking him up a little, but I didn’t think so.”

Longden, an expressionless gnome, said he’d want Your Host to have another chance before he would be convinced the colt couldn’t go a mile and a quarter. “I didn’t worry when Mr. Trouble went past me the first time,” he said. “I was pretty sure we could take him again. But I can’t understand Your Host. He tossed it up coming into the stretch. Yeh, I’m a little disappointed. I thought he’d do better.”

Newspapermen and photographers clamored through the jockeys’ quarters, stumbling over benches, clambering onto one another. While they waited for Boland, Doug Dodson, who had ridden Mr. Trouble, explained that he was forced to make his move earlier than he’d wanted. Your Host’s pursuers began to crowd him going to the far turn, he said, and he feared that if he waited he’d find himself with no place to go. So he took the lead from Your Host and finished him, but the battle finished Mr. Trouble.

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Then Boland came in and there was a rush to his corner of the room. A jock who was nearly trampled looked up and muttered wryly: “Gosh, looks like somebody win something.”

Boland is an immature kid with a lean, unsmiling face, ice-blue eyes, and wavy blond hair. The cameramen hollered to him and turned him this way and that and he complied reluctantly, never relaxing. They kept calling for a great big smile and he’d give them the faintest twisted grin, showing widely spaced teeth out of one corner of his mouth. He was in a hurry to get it over with. And you couldn’t tell whether he was scared or bewildered or utterly indifferent.

His words were barely audible when he said he’d thought he was the winner in the upper stretch, but wasn’t sure until he was home. He broke away from the shouting photographers, saying he wanted his shower.

He wore the same dead pan that had been on his face two days before when he sat in front of the King Ranch barn beyond the backstretch, staring straight ahead while a horseman came up and said to Max Hirsch: “Can I ride your boy on my filly in the stake tomorrow?”

“Is she a kind filly?” Max had asked. “Gentle?” Like a father solicitous of his small son.

“She’s got very nice manners,” the man had said. “She’s very well behaved.”

“All right,” Max had said, and the man had gone away. He hadn’t looked at Willie. Willie hadn’t looked at him. But yesterday Willie won the Kentucky Oaks with the man’s filly, Ari’s Mona, earning $2,100 for himself. Last Saturday, getting his first stakes victory with Better Self in the Gallant Fox Handicap, he’d picked up something more than $4,000. And the jockey’s 10 percent of today’s purse was $9,265.

It’s been a fair week for Willie.

A few minutes after the jockey room was cleared of its confusion, four people were seen walking down the track toward the backstretch stables. Hiking along just inside the clubhouse rail was a kid in a peaked cloth cap and leather windbreaker, with blue jeans clinging tightly to bowed legs. He carried one red rose from Middleground’s blanket.

The thousand who saw him pass didn’t recognize the kid who’d just won the Derby.