John from Long Island, N.Y., stopped by City Hall this morning to meet Mayor Tom Scribner and City staff. "I'm a loser — this is why I'm here," he told us. 

To clarify, John (at right in the above photo with the mayor) finished in last place in his 10-team fantasy football league last year. In this dynasty league, which has been running since 2021, each season's loser is subjected to a punishment chosen by the other team owners. 

Previous years' penalties have included ordeals like sitting in an IHOP from open to close (although one hour was taken off for each pancake the person ate). The punishment for the current season's last-place finisher will be having to make 1,000 free throws and not being allowed to stop shooting the basketball until the target tally is met.

The penalty for his last-place 2023 team? John would have to undergo a trip planned by his friends, in which they sought to subject him to a deliberately lengthy air travel route from John F. Kennedy International Airport to an obscure small town, including the longest possible layovers. As a bonus, however, if John was able to meet the mayor of that city, his friends would cover all his travel expenses.

John didn't know where he would be sent until he received his boarding pass Wednesday night, so he didn't have much time to research his destination. Waiting at JFK for his plane to Seattle early Thursday morning, he thought, "What am I going to do in Walla Walla?"

He arrived here via the mid-day flight and was immediately struck by the size of the terminal. "It's the smallest airport I've ever seen," he said, adding that he found he actually prefers the efficient Walla Walla Regional Airport to the mammoth, chaotic JFK.

John decided he didn't just want to spend his 24-hour stopover sitting in a hotel room, so he's made his time here count. He's done some wine tasting (including enjoying his first-ever wine slushy), did sightseeing throughout the city, visited restaurants and bars, and toured the Whitman College campus. He also called City Hall to arrange a meetup with Mayor Scribner so his friends would have to make good on their promise to underwrite the trip. After the mayor presented him with a City of Walla Walla pin, John texted photos to his buddies, who he said couldn't believe he'd actually been able to pull off the feat.

John told us Walla Walla reminds him of quaint places he's visited in Upstate New York, and said he's found this to be a "very lovely town" where everyone he's met has been "super nice." 

To the irritation of his friends back on Long Island, the trip has been more of a vacation than a torture. He's had a great time and can't say anything bad about his visit.

"It doesn't feel like a punishment because everything's been amazing," he said.

This afternoon, John will fly to Seattle for an eight-hour layover before the return trip to New York. When he gets there, he plans to tell everyone he really likes Walla Walla, and he'll suggest to his girlfriend that they make another visit here together.

"Thank you for honoring my weird request," John said. "I look forward to coming back."