The two-time NASCAR champion was caught in an accident at Dover International Raceway on Sunday, ruining his race after 17 laps. He finished 41st for his fourth poor finish in five races.
Now he's perilously close to the Chase cutoff point.
Some relief comes Wednesday night when Stewart swings open the gates at Eldora Speedway for his annual charity event at his Ohio dirt track.
"You get to do something different that's no stress and it's all about having fun," he said, referring to the Prelude to the Dream race.
Stewart is 11th in the standings, just 35 points from slipping out of championship contention. He's been there once before, in 2006 when he failed to qualify for the Chase and was ineligible to defend his Cup title.
It's far too early to predict the same thing will happen to Stewart this year. But if his luck doesn't change soon, Stewart and his No. 20 team will be in for a long summer.
Of course, the summer is usually when Stewart heats up. In his nine previous seasons, he's scored his first victory before the 14th race of the year only four times. In 2003, his first win of the year came in the 14th event, at Pocono Raceway, where Stewart heads this weekend.
He'll go there trying to shake the hex he's seemingly been under since Talladega, where he revealed he's exploring opportunities away from Joe Gibbs Racing. Since then, a fourth-place finish at Richmond in early May is about the only thing that's gone right for Stewart.
He led 61 laps at Talladega, only to be caught in a wreck 14 laps from the finish and wound up 38th. Two races later, he was wrecked by Elliott Sadler two laps into the Darlington event and finished 21st.
A flat tire with three laps to go -- and the lead -- snatched the Coca-Cola 600 win away from him at Charlotte, and he again was involved in an accident with Sadler just 17 laps into Sunday's race at Dover.
"I take 100 percent responsibility. It's my fault for being even anywhere close to Elliott," a sarcastic Stewart offered. "If I'm within a half a lap of him, I expect that to happen."
But staying away from Sadler might not be the solution Stewart needs to save his season.
Rather, Stewart needs to shore up his future plans so everyone around him can focus on finally getting into Victory Lane this season.
Crew chief Greg Zipadelli has acknowledged that Stewart's situation is a distraction based on the daily questions he receives about the team's future. The core group that started that team in 1999 is still intact, and when the driver is considering leaving, everyone gets a little unsettled.
"Every guy on my team, everybody at the shop wants to know who is what and where, and what's going on," Zipadelli said. "Everybody in the media wants to know what's going on. It doesn't matter where you go or what you do, somebody wants to ask you something about it.
"As tough as you think you are, as cool as you think you can be, when it gets brought up every day, it's a distraction."
Zipadelli knows how tough it is to beat the best in the business, and right now the top competition is under the same JGR roof. Kyle Busch on Sunday won for the fourth time this season -- a series best -- and Denny Hamlin has been to Victory Lane once already.
To win their third title together, Stewart must settle his team and help put the focus back on winning.
"I can't control this," Zipadelli said. "I didn't start it, but it's certainly a little bit of a distraction and that's just the way it is. The teams that don't have distractions and are focused 110 percent, those are the teams that are tough to beat."
In fairness to Stewart, there's little he can do to control this rash of bad luck. It won't matter if he signs a contract extension with Gibbs tomorrow or announces his intention to leave the team. If he's in the wrong place at the wrong time, he's going to crash.
But it's also not a reach to wonder if this sudden slide is at all related to his off-track negotiating. Team president J.D. Gibbs doesn't think so, noting that Stewart and the No. 20 team usually perform at their highest when the chaos around them is greatest.
Yet Gibbs admits the waiting game can be agonizing.
"There's something sitting there. How long is it going to sit there? That's frustrating and those guys want direction for the future," Gibbs said.
So Stewart needs to get through his event at Eldora, where he hopes to raise $1 million to give to Kyle Petty toward construction on a new camp in Kansas City for chronically ill children. Then he needs to sort out his plans because dragging this out much longer might certainly sink his season.
Wilhelmsson Surprised By Raúl’s Spain Absence
Busch wins fourth Cup race at Dover
