The afternoon after Cocoa officially became Willy's, Willy decided to ride Cocoa for the first time. He saddled and bridled him up, then led him outside and mounted. He looked down. "Let's see," he said to himself. "Heels down, legs just so, spine straight…check. Pick up the reins, the leather going under your first three fingers and above your pinky finger…always wondered why that is. Make a fist. Okay." He smiled. He had replaced his top hat with a riding helmet, but other than that he was dressed the way he always did. "Let's go boy," he said, squeezing Cocoa's sides. Charlie, his family, and the oompa-loompas watched as Willy rode around the paddock. He seemed pretty comfortable as he and Cocoa walked, trotted, and cantered around. Willy had even had the oompa-loompas set up a few jumps and popped Cocoa over them. Everything was going great until suddenly a squirrel raced out in front of Cocoa. Cocoa squealed and bolted. Willy tried to stop Cocoa, but he couldn't. Cocoa careened around a corner and out of sight. Charlie rushed around the building to see Cocoa headed straight for him. Willy frantically pulled on the reins and managed to turn Cocoa away from Charlie. But he also aimed him towards one of the jumps. Charlie watched as horse and rider headed straight for the jump. Cocoa leaped over the jump and caught Willy unprepared. Off he flew. He landed on the ground with a thump. "Willy!" he cried, racing to his friend.

Willy groaned and tried to sit up. His leg was bent under him in a funny position. He managed a weak smile at Charlie. "Ow!" he said. "That hurt worse than banging into the elevator."

"Are you all right?" Charlie asked, kneeling by his fallen friend.

"I…think so," Willy said. Cocoa had calmed down his mad flight and came over. He gently nuzzled Willy and nickered softly as if to apologize for dumping him on the ground. Willy pulled himself up further and then slumped back, wincing. "Maybe not. I think I did something to my leg."

One of the oompa-loompas ran to get the doctor and in a few minutes he was back and diagnosed Willy with having a broken leg. Several oompa-loompas ran off and came back with a stretcher. Mr. and Mrs. Bucket helped Willy onto it and he was taken to the factory's hospital.