'Wheel of Fortune' player loses $50,000 to tricky puzzle — fans call it 'quite a tough one'

Even host Ryan Seacrest admitted the puzzle was tricky to solve with the given letters.

PUBLISHED FEB 7, 2026

Screenshot showing James Roberson attempting his Bonus Round puzzle (Cover image source: YouTube/Wheel Of Fortune)

It has become increasingly common for "Wheel of Fortune" contestants to disappoint fans in the final round, no matter how well they perform in the rest of the rounds. One such player painfully lost out on taking home a $50,000 prize after a tricky Bonus Round puzzle stumped him. James Roberson, who played like a pro to win exotic trips and more than $19,000 in cash by the time he reached the finale. However, he couldn't keep the momentum going after being dealt a tough hand. While fans called out the unusual puzzle, even the host, Ryan Seacrest, admitted that the Roberson didn't have enough clues on the board.

Screenshot showing the player's reaction to the loss (Image source: YouTube/Wheel Of Fortune)

In the episode, Roberson, a fan of 90’s TV shows and a great taco chef from Lynwood, Illinois, went up against Conner Custodio, a performance coach from Lakeland, Florida, and Jaque Seckinger, a mom of three boys from Clovis, California. He got off to a flyer by cracking the very first puzzle of the night to add $3,550 to his purse. However, Custodio and Seckinger soon fought back, and the three kept trading the lead through the rounds. After the 'Mystery Round,' the fight for the lead was between Roberson and Seckinger.

The two leaders went into the 'Express Round' with over $3,000 and $6,000 in cash. It looked like Seckinger had it in the bag, but she fumbled the prize puzzle, only for Roberson to pick up the pieces. He correctly guessed, "The pearl of the Pacific," to win an exotic trip to the Westin Bora Bora Resort & Spa, worth $14,000, as per Andy Nguyen's blog. He took the clear lead with $17,000 in cash as Seckinger trailed behind with $6,950. In the Triple Toss Up round, Custodia had a real chance to get back in the game, but he couldn't get a clean sweep, and Roberson preserved his lead to win the night with over $19,000 in cash and the trip.

Screenshot showing Roberson alongside Seacrest at the wheel (Image source: YouTube/Wheel Of Fortune)

Advancing to the Bonus Round, Roberson chose the category, "What Are You Wearing?" and joined Seacrest at the wheel. He then spun the wheel and picked out his Golden Envelope, before walking up to the puzzle board. With the standard letters, "R, S, T, L, N, E," on the board, Roberson chose "G, C, M, and O" as his additional letters. His letter picks didn't give him much as the puzzle read, "_ C _ _ C O _ T _ _ T." After Seacrest kicked off the ten-second timer, the contestant looked completely stumped as he couldn't figure out a single word. "That's a tricky one with those letters," Seacrest said as the timer ran out. He then revealed the answer: "A Chic Outfit".

Screenshot showing the player's total winnings (Image source: YouTube/Wheel Of Fortune)

The host then flipped the golden envelope to show the player he lost out on a $50,000 bonus, which would have taken his total to about $80,000. While the player walked away with a smile, fans weren't too happy. "That’s quite a tough one," wrote one fan, @Colecooper-r5, in the comments of the show's YouTube clip. "Failed mission for the chic outfit... thought it was COZY OUTFIT, now after extra letters showed up, it now changes my answer. CHIC is really tricky one for 50 grand!" added another fan, @robertclimate1563.