'Wheel of Fortune' contestant loses $40,000 in 'painful' bonus round leaving fans heartbroken
Even the host, Ryan Seacrest was surprised to see the good player lose out.
Dec. 24 2025, Published 1:55 a.m. ET
A contestant on "Wheel of Fortune" left fans and host Ryan Seacrest with a sour feeling after losing $40,000 on a seemingly tricky puzzle. The player, Caleb Trent, who was regarded as a 'great player' by the host for his performance during the 'Toss Up' rounds, was stumped by a single word in the Bonus Round. While he still walked away with nearly $28,000, fans yearned for an early Christmas win.
In the episode, Trent, a cookie baker, knitter, and crocheter from Winter Garden, Florida, went up against Monica Flores, an avid golfer from Gilroy, California, and Dana Collins, whose mom named Mary Christmas, from Aynor, South Carolina. He had a rough start as he landed on the Bankrupt Wedge instantly after the introductory round. However, he gathered himself quickly to solve a couple of puzzles, including the PR Round puzzle, to win $13,000. He kept his winning ways up, going into the Express Round, where he solved the puzzle "A Taste Of The Good Life" to win $2,550 in cash and a Collette Christmas tour of London worth $8,298, according to Andy Nguyen's blog. In the Triple Toss-up round, Trent nearly got a sweep by solving two out of the three puzzles to end up as the big winner with a total of $27,848 in cash and the trip.
Going into the Bonus Round, he picked the tricky category, "Place," for his final puzzle and joined Seacrest at the wheel. He didn't bring anyone to the stage, but he got support and compliments from the host, who called him "a good player" for solving the Toss Up puzzles so quickly. Trent then spun the wheel and picked out his Golden Envelope to face a two-word puzzle on the board.
After co-host Vanna White uncovered the standard letters, "R, S, T, L, N, E," on the board, Trent went on to choose the additional letters "P, C, M," and "O" to get more clues on the board. While he got a couple more letters in the puzzle, he didn't have any letter that would outright give away the answer. Thus, with the puzzle reading, "M _ _ N _ O _ L E _ _ R _," the player had his work cut out. After Seacrest kicked off the ten-second timer, Trent got the first word, "Main," but struggled to crack the second one. While he guessed, "Cafeteria, Collector, Corridor," none of them fit. In the end, Seacrest revealed that the puzzle was "Main Boulevard" and that the player had lost out on taking home an additional $40,000. "You needed a 'B' or something to get you on that track," Seacrest said to console the player.
Watch his reaction here.
It wasn't only Trent who was disappointed, but the fans were equally upset. "Another painful, tough puzzle. Enough choosing a place. SMH," wrote one fan, @myles-spikewebby8519 in the comments of the show's YouTube clip. "Tough loss, yes, not as brutal as last night. It's sad that this Christmas holiday week, we see nobody win in the bonus round. That is possible, but let's hope not," added @danielblock6876.
"I figured it out thanks to the "M" that gave me a fighting chance to figure it out. If Caleb had added a 'B,' then that would've done it," suggested @jacobwilson6192.
More on Market Realist: