“Two paths generally lead here. One is an obsession with cars and road trips. The other is an obsession with police countermeasures. If you like either, this is the holy grail.”

The technology has improved, but the basics haven’t changed. The race starts at the Red Ball Garage on 31st Street in New York and ends at the Portofino Hotel and Marina in Los Angeles. The details and date are shared only discreetly. Speed limits are routinely ignored, and the event still attracts a cast of characters as colorful as ever.

Cherkassky, 40, runs his own small business outside Philadelphia, has a wife and two children. He moved to the United States at 14 from the area that’s now the Ukraine.

“They told us to hate this country,” he said of his childhood. “They said you should be grateful to God you were born in USSR. But this country gave me everything I have.”

The race was a chance to take in the entire country, to search its hills and valleys and all the space that fills the giant divisive gaps separating the Donald Trump billboards in Indiana and Hillary Clinton bumper stickers in California. Drivers and organizers prefer to call it a “run,” not a race, and it’s a search for country and possibility as much as it is a search for self.

In addition to Cherkassky, four other teams would be on the road: a tactical group dressed as Blues Brothers driving a replica of the Bluesmobile; a veteran team in a Lincoln Continental with a unique waste-disposal system and a secret weapon in the back seat; a long-haired Brooklyn man who would find his journey interrupted by a police K-9 unit; and a pair of brothers from the Midwest who had more than 20,000 songs loaded on an iPod and a booming sound system in their van that they hoped would rock them from coast to coast.

They all had to leave to the Red Ball Garage in the same 24-hour period, getting a time stamp they’d carry across the country. Cherkassky and his 33-year-old Mercedes — price tag: $2,800 — were the first in the garage on a dark September morning, and he was eager to get going. He was the only first-timer in the field, and he had no idea how his car or his body would respond to whatever the next 2,900 miles held.

But he was ready to find out.

Cherkassky snapped a photo in front of the garage with his driving partner, the red neon sign glowing bright in the background, before climbing back in the car.