He finished 42nd on Sunday. He is now 0-for-17 in NASCAR's biggest event.
A numerologist might say Stewart is cursed in February races at Daytona International Speedway. A realist like Stewart just shrugs his shoulders.
"Well," he said, "it's just part of it."
It's always something at the Daytona 500, and the "it" on Sunday was a wreck on the 41st lap.
Stewart was tooling along in the middle of the track when his car slid to the outside. It kissed the wall and triggered a five-car wreck. The steering was damaged in Stewart's Chevrolet. After sitting on pit row for a few minutes hoping for a quick fix, mechanics decided to haul the car to the garage.
So at least Stewart's latest Daytona pill was a quick swallow. It also spoiled one of the popular storylines going into the race.
Along with Jeff Gordon winning in his final 500-mile race at Daytona, a lot of fan were hoping Stewart would win his first after all those tries. It would have made a nice comeback tale after two tortured years.
Stewart all but demolished his lower right leg in a short-track race in 2013. He still has a titanium rod to show for it.
Last August his car struck and killed driver Kevin Ward Jr. in a sprint-car race in New York. Ward's family blamed Stewart, but a grand jury exonerated him of any wrongdoing and a toxicology report showed Ward was under the influence of marijuana.
That didn't make the ensuing depression much easier on Stewart. He missed three Sprint Cup races and just went through the motions the rest of the season.
Stewart slowly regained his old sarcastic spunk and declared himself ready to go when he arrived at Daytona. Stewart already has an impressive resume, with 48 Sprint Cup wins and three championships. Winning the "Great American Race" doesn't consume him, but he knows what it would mean.
"That cements your legacy," he said before the race.
Restrictor-plate racing is a great equalizer, often rewarding lesser drivers who avoid trouble and end up in the right place at the right time. But that fickleness does not explain Stewart's struggles.
He's won four of the 400-mile July races at Daytona and has 19 wins overall at the track. That's more than any other active driver.
He was second in 2004 but hasn't had a top-10 finish since 2009. Sunday was the fourth time he's finished 40th or worse.
A fortune-teller might conclude Stewart is cursed. He has 47 more Sprint Cup wins than Trevor Bayne. But Stewart had to watch the 20-year-old Bayne win the Daytona 500 in 2011.
Stewart turned 20 in 1992. Back then, a Daytona winless streak was starting to weigh on Dale Earnhardt. He wouldn't win the 500 for another six years.
That was Earnhardt's 20th try. Almost every pit crew lined up to cheer for him as he drove to Victory Lane.
Stewart is now entering Earnhardt territory. His crew repaired the damage well enough for him to return the track on Sunday. After a couple dozen laps, Stewart pulled back into the pits.
"It's the biggest race of the year," he said. "The last thing you want to do is stay out there and have something else happen to get in the middle of something. Let's just let those guys have their day."
Stewart drove his car to the trailer and started packing up. He left another Daytona 500, wondering if his day will ever come.