Beneath the helmet is another layer: a yarmulke emblazoned with the logo of the University of Maryland.
In two years, Chalupski hopes, he will honor his sport and his Jewish heritage by participating in the Winter Olympics in Russia as the first ever member of Team Israel to race skeleton.
Chalupski wants to be the frozen chosen.
It's not a whim or a flight of fancy. The Maryland graduate doesn't want to be a novelty act, like Eddie the Eagle, Britain's death-defying ski jumper at the 1988 Olympics. Chalupski put a planned legal career on hold and now waits tables to make ends meet.
"I'm an American. I'm a boy from Jersey. But I'm super proud of what I'm doing," said Chalupski, 27. "Wearing the Star of David is a huge responsibility."
Skeleton sliders, as they are called, push their sleds — basically a fiberglass cookie sheet on runners — about 140 feet, gathering speed and then leap on for their run. They steer by shifting their body weight or by dragging their feet, which dangle off the back. The fastest time down Lake Placid's 19-curve track is 53.68 seconds.
Chalupski already has competed in two skeleton world championships and won an America's Cup medal — Israel's first. He is ranked 59th out of 118 this year and finished ninth during the final America's Cup races last weekend. His informal coach, Rebecca Sorensen, a former U.S. skeleton athlete, believes her pupil can finish the 2014 Olympics in the Top 20.
But now comes the hard part: finding the money to launch a campaign that will take him this fall and winter to the world-class competitions in Europe. For that, Chalupski will spend the summer speaking at synagogues and before Jewish community groups to explain his journey.
The presence of a lone Israeli slider has altered the sport's culture. The sound of a shofar horn mingles with the din of cowbells at the starting line, and race officials in Lake Placid — home of the 1932 and 1980 Winter Olympics and a training site for many U.S. teams — had to order a white-and-blue Israeli flag for the ceremonial platforms.
Plunging 70 miles per hour down a track that drops 40 stories wasn't the path Chalupski had in mind in February 2006 as he sat alone in his Allegany Hall dorm room on the College Park campus, watching the Winter Games. Fluent in French, proficient in poker and a euphonium player in the Maryland marching band, he envisioned a career as a public servant in Washington.
All that changed when the skeleton competition came on the screen.
Chalupski recalled saying to himself: "That looks like so much fun. I bet I could totally do that."
A Google search located the website of the U.S. Bobsled and Skeleton Federation and instructions on how to apply. Chalupski filled out the paperwork and sent it in. He graduated with honors in the spring of 2006 and went to France to teach high school English.
Then, in November, an email arrived inviting him to attend skeleton tryouts.
With his mother's reluctant help — "she threw a tantrum," Chalupski said — he flew from Paris to Utah, where he performed well enough to receive an offer to join the U.S. skeleton development program.
Instead, he entered law school at Seton Hall University in New Jersey. He tried to concentrate — but in the end succumbed to the lure of Lake Placid's sliding track. He began dividing his time between the Newark campus and the Adirondack Mountains.
Each winter, Chalupski improved just enough to stay on the team. For his final semester, he stacked all his courses on Mondays so he could spend the rest of the week training for his last big chance on the track: the selection races leading up to the U.S. team trials.
He didn't make it.
"I sold some equipment and was ready to move on," Chalupski says. "I was setting up the other side of my life."
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."
Israel has participated in five Winter Olympics, the first in 1994 in Lillehammer, Norway. An attempt to qualify a bobsled filled with Jewish Americans and Canadians for the 2006 Games failed.
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."