Fate, in the form of Andy Teig, intervened. A paramedic in Lake Placid and a pillar of a local synagogue, Teig also is a retired Israeli bobsledder and CEO of the Israeli Bobsleigh and Skeleton Federation. He had a proposition: "If you think that this is an easy ticket to the Olympics, get out of my face. If you're not serious about Israel, get out of my face. But if you're serious, maybe — maybe — we can talk."
For more than two months, Chalupski agonized over Teig's offer, asking friends and relatives what he should do. He doesn't speak Hebrew and had never visited Israel. Having a Jewish mother and a Catholic father had created many happy holiday smorgasbords but no bedrock religious convictions.
"I had never given any thought to my Jewish heritage other than the fact that I considered myself Jewish," Chalupski said.
His girlfriend, the daughter of an Orthodox rabbi, crystallized the matter.
"You are Jewish and someone is asking you to represent your homeland in a way in which you are uniquely capable of doing," Chana Anolick recalled telling him. "You have a responsibility as a Jewish man to do this."
Chalupski laughed as the story was told. "No pressure," he said.
He laughed again when asked if his mother would be proud of him if he qualifies for the Olympics. "Only if I'm a lawyer who qualifies for the Olympics," he said.
He and Anolick took a "birthright trip" to Israel a year ago and hope to move there some day.
"I did actually wander in the desert and I thought about my ancestors," Chalupski said. "I felt a deep, emotional connection to the land."
Back in Lake Placid, looking at an empty bank account, Chalupski turned for help to a Maryland marching band colleague and fraternity brother, Philip Nathan.
Chalupski recruited Nathan, an accountant, to become the financial officer for the Israeli sledding federation. Nathan said he hopes to mount a fund-raising effort in the Jewish community for the $20,000 it will take to get Chalupski a better sled and send him on the full, eight-race World Cup series starting in the fall.
"We're a very lean organization and we do it without the support of the Israeli government," Nathan said."There's better places for Israel to spend its money right now."
The Israeli Olympic Committee, which gave its blessing to the 2006 bobsled team, has not yet signed off on Chalupski's bid. Like the cash-strapped committees in many small nations, the Israeli group insists that its athletes, even those who have qualified for the Winter Games, be among the world's best in their sport. That requirement prevented figure skater Tamar Katz, the three-time Israeli national champion, from competing in the last Olympics.
Given the dominance of Germans, Latvians and Canadians in skeleton, Chalupski will be hard-pressed to break into the Top 10. But he has time and a growing fan base. Ido Aharoni, Israel's consul general in New York, has posted best wishes to Chalupski on his Facebook page.
And there's Chalupski's talent.
"His knowledge is there. His experience is getting there. He's got what it takes," said Sorensen, a U.S. sliding coach who mentors athletes from smaller nations. "His passion and dedication to the sport oozes out of him. He just wants to go fast."
Even the reluctant Ilene Chalupski has come around to her son's sport.
"I'm proud of him even though I think he's a little crazy," she said. "I don't care which place he comes in. I just want him to stand up at the bottom with all the pieces intact."