History repeats as ‘Wheel of Fortune’ player loses $50K, thanks to same tricky puzzle from 16 years ago

Contestant Lisa Santangelo was presented with a two-word puzzle that could've seen her break a 'Wheel of Fortune' jinx
PUBLISHED SEP 14, 2025
Screenshot of Vanna White and Lisa Santangelo from an episode of 'Wheel of Fortune' (Cover image source: YouTube | Wheel of Fortune)
Screenshot of Vanna White and Lisa Santangelo from an episode of 'Wheel of Fortune' (Cover image source: YouTube | Wheel of Fortune)

Over the years, 'Wheel of Fortune' fans have witnessed many contestants missing out on big prizes due to tricky puzzles. But the puzzle that saw contestant Lisa Santangelo miss out on $50,000 left fans talking for a different reason. It turns out that this was reportedly the same puzzle that saw another contestant miss out on $100,000 in Season 26, back in 2008. Meanwhile, despite her huge setback in the Bonus Round, Santangelo appeared in good spirits and happily walked off the beloved game show with a cash prize of $12,928 and a trip to Hawaii. 

In 'Wheel of Fortune' Season 42, Santangelo, competing against Kamilah Williams and Jared Collier, had a bumpy start. Williams took the early lead by solving the first toss-up puzzle, "Santa Hat". Santangelo, however, bounced back in the Mystery Round by cracking the prize puzzle "An Enchanting World", winning an exotic trip to Hawaii, worth $7,428, as per Andy Nguyen's blog. Santangelo maintained the momentum in the next few rounds and ultimately finished on top of the leaderboard with a total of $12,928 in cash, along with her Hawaii trip.

During the Bonus Round, host Ryan Seacrest asked Santangelo to pick a category for her final puzzle, and she selected 'Person'. Joined on stage by her mother, Santangelo spun the wheel to pick out her Golden Envelope. She was faced with a short two-word puzzle. After Seacrest gave Santangelo the standard letters, R, S, T, L, N, and E, she went on to choose P, C, H, and O as her additional letters to round out the puzzle. With everything on the board, Santangelo's final puzzle read: “_O_ _LE  _ _ ENT.”

As Seacrest started the ten-second timer, Santangelo looked confused. With time ticking down, Santangelo tried her best to guess the puzzle, but could only say, “Oh my gosh, what is it?” before the time ran out. Seacrest's co-host Vanna White revealed that the correct answer to the puzzle was "Double Agent." Even Seacrest admitted that the puzzle was tough. “Yeah, you needed more to work with. I don’t know how you would have gotten there with that," he said, as per Market Realist. Shortly afterward, Seacrest opened the Golden Envelope and revealed that Santangelo missed an additional $50,000 she could have taken home.

As soon as the episode dropped on YouTube, many fans shared their honest thoughts on Santangelo's final puzzle in the comments. One user wrote, "I was stumped on this one, too. Not enough letters! So sorry, Lisa, for not winning the Bonus Round, but Congratulations on your winnings & your fabulous trip to Hawaii!" Another netizen commented, "I only got the Agent part. It was Double Agent. She missed out on $50,000." A third user, however, pointed out something interesting. "Fun fact: This Used For December 29, 2008, During America's Game 2 Caroline Not Solved On Bonus Round And Lost $100,000, And For The Past 16 Years Lisa Not Solved On Bonus Round And Lost $50,000 During Disney Santa Holiday Giveaway," the user wrote.  

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