Wheel Of Fortune Champ Reveals Surprising Reason Why Winning A Bunch Of Trips Isn't So Ideal

Wheel of Fortune has been doing something a little different with the games that air this month on the 2026 TV schedule. In honor of the season of warmer weather that’s upon us, Ryan Seacrest and co. are allowing winning contestants to “spring forward” and continue playing until they lose (much like on Jeopardy!, where Jamie Ding is on a historic 31-game roll). Recent WOF contestant Chad Cabanilla took full advantage of the gameplay twist, but it sounds like winning a bunch of trips may not be as great as you'd imagine.

Chad Cabanilla competed on five episodes of Wheel of Fortune, and given his haul of $183,723 in cash and prizes, I’m sure he’d agree with the consensus calling it one of the best game shows of all time. However, most of that six-figure total came from the value of the trips he won — the SIX trips, to be exact, as Cabanilla told The Mankato Free Press after his fourth win:

That’s quite the comprehensive trip around the world! As well as hitting both sides of the U.S., the Wheel winner could travel to Europe and Asia, then hit the Caribbean and Central America — as long as they can do it quickly. Chad Cabanilla revealed one stipulation regarding the prizes won on Wheel of Fortune that will likely keep him and his husband from hitting all six locales:

While the contestant was excited about his winnings all the same — he’s reportedly an experienced traveler whose husband is a flight attendant — that seems like a huge disadvantage for the average player.

I’m sure having someone win six trips during their Wheel of Fortune experience is a rare occurrence — not likely at all for one-day contestants — but even two big trips within a year’s time can be difficult to schedule for some people.

That’s not even considering the taxes. What a lot of people don’t think about when it comes to Wheel of Fortune is that all of the winnings — cash, vacations, cars, etc. — are taxed like regular income. Past contestants have even swapped their prizes for less-expensive vacations to help offset that tax payment.

I understand Wheel of Fortune’s need to put such stipulations on their all-expenses-paid trips, but it seems like in instances of this “spring forward” special — or really any occasion where a contestant wins numerous trips — there should be an exception written into the rules that they have more time to schedule their vacations. Maybe they could allow the winners to trade such prizes in for a percentage of the cash value.

I wonder if this was an issue that the powers that be at Wheel of Fortune could have foreseen when the “spring forward” idea came up or if they’ve considered changes for the future.

You can see the end of Chad Cabanilla’s run on Wheel of Fortune with either a Hulu subscription or a Peacock subscription. Episodes are available to stream for a limited time starting the day after airing. Check your local listings to see when the game show airs in your area.