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With a record 291 NASCAR Cup Series victories, Hendrick Motorsports is the all-time wins leader among Cup Series organizations. 

Of those victories, eight have come in NASCAR’s biggest race, the Daytona 500 — courtesy of five different drivers. 

So, unless you can recite every Daytona 500 winner — and the team they drove for — over the past decade, you probably assume that Hendrick Motorsports has won The Great American Race in the last handful of years.

That isn’t actually the case, however.

Hendrick Motorsports’ 2014 Daytona 500 win was significant for many reasons

So when did Hendrick Motorsports score its most recent Daytona 500 victory? Well, it was February 23, 2014, and the driver of the race-winning car was Dale Earnhardt Jr., who secured his second triumph in the 500 but first in a car owned by NASCAR Hall of Famer Rick Hendrick.

I’ll personally always remember that day — and night — not just for Dale Jr.’s popular win but for my own personal odyssey and several happenings that made this day different from most days at the track. From the time I was eight years old, covering the Daytona 500 live and in person for a major media outlet had been a dream of mine, and this was the day it finally happened for me — at the age of 30 while working as a NASCAR writer and editor for FOX Sports Digital.

When I arrived at Daytona International Speedway at 7 a.m. on Sunday morning, more than six hours before race time, I had no idea I’d be leaving the track 20 hours later — at 3 a.m. — thanks to multiple weather delays that included not just torrential downpours but heavy winds and a tornado warning for the Daytona Beach area (some folks said a tornado came through the speedway infield, where I was working in the media center along with dozens of other reporters, but I’m not sure that was ever confirmed).

Of course, no one except me cared or was probably even aware that it was my first Daytona 500. All the focus was on the race and, later, the race winner, who led the final 18 laps and 54 of 200 laps in total in his No. 88 Hendrick Motorsports Chevrolet.

When Earnhardt arrived in the media center around midnight for the post-race winner’s press conference, it was the perfect ending to a long but incredible day. I grew up a fan of both Dale Jr. and his legendary father, and although I had abandoned all rooting interests many years before I ever covered my first Daytona 500, it was heartwarming to see the third-generation driver so euphoric over what had just taken place.

Little did I or anyone else know at the time, however, that Hendrick Motorsports would be shut out of Victory Lane at the Daytona 500 for at least the next eight years.

Hendrick Motorsports hopes to end lengthy drought in the Daytona 500

If you think Hendrick Motorsports’ Daytona 500 drought is lost on anyone within the powerhouse organization, well, think again.

Team owner Rick Hendrick, Hendrick Motorsports vice chairman and three-time Daytona 500 winner Jeff Gordon, and, in all likelihood, all four Hendrick drivers — Chase Elliott, Kyle Larson, William Byron, and Alex Bowman — are especially cognizant of how long it’s been since a Hendrick driver last hoisted the coveted Harley J. Earl trophy awarded to Daytona 500 winners.

“I don’t know why that just struck me this offseason when I started thinking about going to Daytona and the preparations for it,” Gordon said last week on Sirius XM NASCAR Radio. “It’s been a while. It’s been a while since we’ve won a Daytona 500 but almost even really competed for a Daytona 500. We go down there and sit on the pole and are super-fast, but once we get in the 500, we’ve just not been able to get ourselves aligned and get position, and that’s what it takes. It takes a lot of effort with your teammates, it takes a lot of effort with finding some other folks to work with, it’s strategy, it’s staying out of trouble, it’s so many things.”

As a driver, Gordon won the Daytona 500 in 1997, 1999, and 2005 but came up short in his final 10 attempts to prevail in the season opener on Daytona’s fabled high banks. All four of Hendrick Motorsports’ current drivers are still searching for their first Daytona 500 win.

“I look back at my career and think about this: I won three Daytona 500s, but they were all within about the first 10 years of my career of 23 years,” Gordon said on Sirius. “2005 was the last one. So you go through these cycles of when things are coming together, the cars are right and you’re staying out of trouble and doing all these things, but the same things apply — they were super-hard to win back then. 

“But it just seems like right now we’re in this cycle where we’ve not really been putting ourselves in position. So there’s a lot of effort, a lot of energy and a lot of excitement to go down there for all of us, and I know Rick would love to have that, too, because it does seem like it’s been a little while since we’ve pulled that off.”

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