November 6, 2026

Windham resident to compete in ‘Million Dollar Affordability Showdown’

By Ed Pierce

Kaullen Winter of Windham is one of just 12 nationwide finalists set to compete in the “Million Dollar Affordability Showdown” in Georgia and a chance to walk away with a $1 million prize.

Kaullen Winter of Windham, right, is one of
12 nationwide finalists competing in Atlanta,
Georgia in the 'Million Dollar Affordability
Showdown' and hopes to win a $1 million
prize for his wife, Kassaundra, and their
family.  SUBMITTED PHOTO
Winter, 32, works for Cintas in Westbrook as a maintenance technician and has worked as a maintenance technician for the past 13 years. He first heard about the contest while online.

“I found the program via an ad on Instagram I believe,” he said. “There was a commercial or reel that was talking about the affordability crisis and if we thought we knew why everything is so expensive. All I had to do was take a quiz and I would be entered in a sweepstakes drawing to compete in Atlanta for the grand prize of $1 million.”

The “Million Dollar Affordability Showdown” is held in Atlanta, Georgia and is the culmination of “The Million Dollar Question,” a national initiative that challenged Americans on their knowledge of economics, affordability and the issues affecting everyday life.

As just one contestant out of hundreds of thousands of participants from across the country, Winter made it to the final 12 contestants and will be flown to Atlanta to compete in the live competition. This summer, he answered questions at the “Million Dollar Question Official Site” covering a range of affordability topics like housing, wages, healthcare, groceries, childcare, and government spending.

The “Million Dollar Affordability Showdown” contest is sponsored by The Foundation for Economic Education (FEE) which launched a national campaign asking Americans a question they're already asking themselves: "What's Behind the Affordability Crisis?"

The questions that were posed in the online quiz this summer were designed to enable respondents to understand the economic forces causing America's affordability problems such as inflation, tariffs, indebtedness and soaring interest rates.

National finalists were randomly selected by The Foundation for Economic Education to compete in the "Affordability Showdown" game show taped finale in Atlanta hosted by comedian and political satirist Andrew Heaton.

"Affordability problems are often bottleneck problems," said Diogo Costa, FEE's President. "If we do not build enough homes, train enough doctors, produce enough energy, or make it easier for businesses to serve people, the result shows up as higher prices and tighter family budgets. The ‘Million Dollar Question’ asks Americans to look at the bottlenecks behind the bills."

For FEE, the contest is a bridge to teach Americans about the real economics behind rising costs of living, Costa said.

Founded in 1946, FEE has been helping Americans understand the real economics behind what they're living through. FEE’s mission is to inspire, educate, and connect future leaders with the economic, ethical, and legal principles of a free society. These principles include: individual liberty, free-market economics, entrepreneurship, private property, high moral character, and limited government.

"Affordability isn't abstract," Heaton said. "It's rent, groceries, childcare – stuff people deal with every day. This quiz turns that daily pressure into a national conversation and, for 12 people, into a shot at the Affordability Showdown finale in Atlanta with a $1 million prize."

Winter says he has no expectations for the national finals but welcomes the opportunity to travel to Atlanta. 

“I hope to win it all more than anything, but enjoying the free vacation is also part of the experience,” he said.

As the father of five young girls, Winter spends a lot of time when he’s not working playing with his children, playing video games, working on equipment, and enjoying whatever life has to offer.

He says he’s looking forward to competing in the “Million Dollar Affordability Showdown.” Taping of the national finals will take place later this month.

“New experiences are always a bonus,” Winter said. <

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