Reality show fan loses $40K on ‘Wheel of Fortune’ — but still wins a trip she’s dreamed of her whole life

“We grew up having meals around Christmas at Olive Garden, and ever since then, I’ve wanted to go there,” the 'Wheel of Fortune' contestant said
PUBLISHED JUL 26, 2025
Host Ryan Seacrest with contestant Grace Hamilton on the sets of 'Wheel of Fortune' (Cover Image Source: YouTube | Wheel of Fortune)
Host Ryan Seacrest with contestant Grace Hamilton on the sets of 'Wheel of Fortune' (Cover Image Source: YouTube | Wheel of Fortune)

Wheel of Fortune’ has a record of making dreams come true! Grace Hamilton fulfilled her dream after winning a trip to Italy on the game show. The contestant competed against Derek Houk, from Spokane Valley, Washington, and Takesha Butler, from Columbia, South Carolina. The Westcliffe, Colorado, native had a rough start and even landed once on ‘Bankrupt,’ but she somehow found her way to victory. Hamilton, a reality show lover, solved the second toss-up round and earned $2000 in her bank. She also solved the first puzzle — “Simply Perfect” — and had a total of $4,250 in her bank. But unfortunately, she landed on ‘Bankrupt’ and lost all her money.

However, after solving the puzzle “Search for the Best Gelato,” and it brought her total amount to $13,850. She also solved two toss-ups back to back and earned an extra $4000. At this point, Houk had a total of $7,900, and Butler was only left with $7,900. Hamilton won by a huge margin with $17,850 cash prize and a trip to Italy. She finally made it to the Bonus Round to try and win an additional cash prize. Hamilton selected ‘Thing’ as her category for the final round. After ‘Wheel’ gave her “R,S,T,L,N, and E,” and she selected the letters “C,H,M, and A,” the puzzle she was left with was: “_ _ _LTE_  _A_R_C.”


 
 
 
 
 
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She kept decoding the puzzle but couldn’t guess it before the time ran out. The puzzle was revealed to be: “Quilted Fabric.” Since Hamilton couldn’t guess the puzzle, she lost an additional $40,000 cash prize. Nevertheless, she was happy to be able to tick one thing off her bucket list, and that is a trip to Italy. After the show, the contestant was interviewed by the show’s social correspondent, Maggie Sajak, daughter of retired host Pat Sajak. “You’re an adventurous person. You’re going to be taking a trip to Italy soon,” Maggie said.

“I’ve wanted to go to Italy my whole life,” Hamilton revealed. “We grew up having meals around Christmas at Olive Garden, and ever since then, I’ve wanted to go there,” she added. “The endless breadsticks in Italy are even better,” Maggie told the contestant. The show has fulfilled many contestants’ wishes either by allowing them to be part of the game show or through cash prizes and trips. Erika Hilliard, a 56-year-old mother, military spouse, and lifelong fan of the show, fulfilled her dream of being on ‘Wheel of Fortune.’

“I grew up watching Wheel of Fortune, no matter where we were living—Germany, Texas, Louisiana—I always found a way to tune in. It’s always been a part of my life,” Hilliard said during a wide-ranging interview on Mic Check w/ Micah. “You walk onto that set, and it’s like you’ve stepped inside your television. The lights, the wheel, the energy—it’s magical,” she added. She admitted that it took a while for her to process everything that happened on the show. “It still doesn’t feel real,” she said in the interview at the time.

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