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Come Fan with UsSaturday, June 20, 2026

Tony Stewart’s retirement costs NASCAR another iconic figure

Following Jeff Gordon’s January announcement that his NASCAR career was ending, Tony Stewart is preparing to do the same on Wednesday.

Within the span of nine months, two of NASCAR’s all-time greats have announced their pending retirements. Jeff Gordon will step aside at the conclusion of the current season, while Tony Stewart will do so following the 2016 season.

That Gordon is preceding Stewart into retirement is somewhat appropriate, as it was Gordon’s success in transitioning from open-wheel sprint car racing to NASCAR that allowed Stewart to make a similar conversion.

Both hail from Indiana -- Gordon from Pittsboro by way of California, Stewart is from Rushville -- and cut their teeth driving high-powered sprint cars throughout the Midwest. Each dreamed of Indianapolis 500 glory, but only Stewart would get a chance to compete premier open-wheel race in the United States, as a lack of money and prospects pushed Gordon to pursue a career in NASCAR, then a primarily Southeastern-based racing series.

Though an outsider, Gordon through sheer talent adapted to the switch rather quickly. He would win a Cup Series championship by his third season with two more over the next three.

Meanwhile, Stewart obtained the chance Gordon never did, thanks to the formation of the Indy Racing League. The brainchild of then Indianapolis Motor Speedway president Tony George, the IRL was conceptualized as the Indy car equivalent of NASCAR emphasizing oval racing and America born drivers.

The poster boy of the fledgling series was Stewart, who came through the USAC sprint car ranks. But because he didn’t have the funds to cut a big check, Stewart could never land a CART ride -- what was then the top open-wheel series in North America.

But the IRL provided Stewart his opportunity and soon his mammoth talent became obvious for all to see. He won the championship in his second season and finished third overall the next.

The formation of the IRL, however, created a contentious rift within open-wheel racing. A once burgeoning form of motor sport that surpassed NASCAR in appeal and television ratings suffered an instantaneous drop in popularity. Coinciding with that collapse was NASCAR’s ascent to unprecedented heights thanks in large part to the arrival of a one-time Indiana sprint car driver, who now wheeled a brightly colored No. 24 car.

NASCAR’s upward trajectory and the ruinous IRL-CART civil war had another consequence -- Stewart abandoned his open-wheel passion for the riches of stock car racing. After dabbling part-time, he made the permanent move in 1999 winning the Cup Series Rookie of the Year on the strength of rookie record three victories.

Joining Gordon, Stewart would rise to become one of NASCAR’s prominent figures -- on and off the track. Between them they would win six championships over an 11-year span (1995-2005) and helped fill the considerable void following the death of Dale Earnhardt Sr. on the final lap of the 2001 Daytona 500. And the pair of Hoosiers would come to characterize the diametric sides of NASCAR has it ushered in an era of extraordinary growth.

The man with the model wife and largely squeaky-clean image, Gordon represented the “new NASCAR,” a driver as comfortable hobnobbing sponsors on Madison Ave. as making passes at Talladega. Multiple times he would serve as a guest on daytime television and even once hosted Saturday Night Live.

Stewart was the everyman, whose love of sprint car racing on dusty short tracks, cantankerous nature and yearning to just drive and not play the games associated with the courting of Fortune 500 companies resonated with NASCAR’s blue-collar fan base.

Many fans saw Stewart as a throwback to when driver’s weren’t worried about offending sponsors and freely expressed themselves. And even as he became a multi-millionaire many times over, owned a spectrum of race teams in variety of disciplines and barnstormed throughout the country on a private plane, Stewart was able to maintain this image.

But whereas Gordon, with the exception of a 2002 public divorce, mostly skirted controversy, Stewart seemed to invite public scrutiny. Mercurial and sometimes volatile, he shoved a photographer following the 2002 Brickyard 400, an act that earned him a 25-point penalty and $50,000 fine. He once kicked a reporter’s tape recorder underneath a car at Daytona and argued with officials about needing to wear a head-and-neck restraint device at Talladega.

And last year, Stewart struck and killed another racer, Kevin Ward Jr., during a sprint car race in Upstate New York. A grand jury would clear Stewart of any criminal wrongdoing, but the Ward family claims he acted recklessly and filed a wrongful death lawsuit against Stewart in August.

In a myriad of ways, Stewart was the modern-day equivalent of his idol A.J. Foyt, whose No. 14 Stewart chose to use when he formed Stewart-Haas Racing in 2008. If it had wheels and an engine, Foyt and Stewart would find a way to go fast and often win, but also left those around them flummoxed by sometimes boorish behavior.

Nonetheless, Stewart’s popularity remained strong and the tribulations of the last few years have in a way turned him into a sympathetic figure. He’s spoken candidly on how Ward’s death has affected him deeply and will continue to do so going forward.

But Stewart’s time as a NASCAR driver is coming to an end, just as Gordon is set to walk away. Though they both will continue to have a presence -- Stewart as a team owner, Gordon as a television analyst -- stock car racing will miss the aura each brought every weekend. You simply don’t replace a Gordon or Stewart, two of the sport’s absolute best.

The once prodigious young sprint car drivers from Indiana that were once groundbreakers are now elder statesmen, who have begun their white flag lap.

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