Kyle Busch's most heartbreaking Daytona 500 losses

Despite winning 63 NASCAR Cup Series races and two championships, NASCAR's greatest prize has always eluded Kyle Busch. 

The future Hall of Famer has yet to win the "Great American Race" in 20 tries and will gear up for his 21st start in the event on Feb. 15. 

Here are his four most heartbreaking losses in the Daytona 500. 

2023: Leading at the 500-mile mark 

If there was ever a Hollywood story that was going to play out in the 2023 Daytona 500, this was it. Busch, in his first race with Richard Childress Racing — the same team Dale Earnhardt finally exorcised his Daytona 500 demons with in 1998 — was leading in the closing laps until a spin from Daniel Suarez re-racked the field for an overtime restart. 

Busch led under caution at the 500-mile mark, just as Earnhardt had done 25 years earlier. But unlike Earnhardt, Busch had to race for two more laps, and Ricky Stenhouse Jr. went on to win as Busch fell to 19th after being involved in a last-lap crash.

2019: Runner-up to a JGR teammate 

2019 ended up being the second championship season for Busch in a five-year run that saw him win two titles, 27 races and advance to the Championship 4 five times. 

But even at his peak, Busch still couldn't snag a Harley J. Earl trophy. His Joe Gibbs Racing teammate, Denny Hamlin, won the race, while Busch finished second, earning his best Daytona 500 finish.

2009: Late crash takes out a fast car 

Even after a late-season collapse in 2008 dropped him to 10th in the final standings, expectations were still high for Busch going into 2009. His first season with Joe Gibbs Racing had yielded eight victories, and he nearly started 2009 with another one. 

Busch led 88 laps — the most he's led in a Daytona 500 to date — but was involved in a huge crash on Lap 124 and finished 41st in a rain-shortened event that Matt Kenseth went on to win. 

2008: So close, yet so far

Busch had already made a name for himself at Daytona by the time the 2008 Daytona 500 rolled around. He ran up front all day in the 2007 running of the race before losing a heartbreaker at Daytona to Jamie McMurray in July 2007. But in his first race with Joe Gibbs Racing, he was once again fast, leading 86 laps. 

2008 is most remembered for arguably being Tony Stewart's best chance at a Daytona 500 win — a victory he never got. But Busch, who finished fourth, also left Daytona heartbroken after the Penske teammates of Ryan Newman and Kyle's brother, Kurt, drafted past Stewart and Kyle Busch to give Roger Penske a 1-2 finish in the 50th running of the "Great American Race."