Critical Path Security 2026 5 Drivers to Watch: Daytona Speedweeks

Today is the day. The first official points race of the 2026 NASCAR season is upon us. No, the Duels at Daytona do not count as points race even though the Top-10 of each race receive points. Anyway, the Craftsman Truck Series kicks off the “official” festivities with the Fresh from Florida 250 under the lights. On Valentine’s Day, the rebranded O’Reilly Auto Parts Series will also race under the lights. Then, the Great American Race takes racing’s center stage as the 41 Cup drivers will look to add their names to the Harley J Earl trophy. NASCAR racing is back and a long season awaits. However, it is a welcome time after the doomsday offseason that NASCAR ventured through. Along with the return of racing is the return of the weekly Drivers to Watch series. Critical Path Security is gracious enough to continue their sponsorship of Drivers to Watch and Pit Pass Network is grateful. To kick off the 2026 season, it is time for the Critical Path Security 5 Drivers to Watch for Daytona Speedweeks.

For some housekeeping before heading into the meat of the article, this year will be 5 drivers instead of 6. Instead of featuring an even number of drivers from each series, these articles will highlight the most intriguing, notable, or underdeveloped stories/drivers for each weekend across NASCAR’s top 3 series. Some weeks, it will be a balanced split. Others, you might see only one series featured. The 2026 season will dictate who is featured each week. Similar to the prior years, the goal is to highlight some drivers who fly under the radar. This series is not to have the same 4-5 drivers appear weekly.

Tony Stewart

Although sometimes, the obvious choice is the right one to write about. In a stacked field for the Fresh from Florida 250, there is no one more surprising on the entry list than Tony Stewart. Making his first NASCAR start since 2016 (and his first Truck start since 2013), Kaulig Racing’s All-Star entry is kicking off with a bang. While the exact speed of the RAM trucks is not known yet, Stewart is a master of working the highbanks of Daytona. Though he never won the big one, Stewart has racked up 11 Daytona wins between the Cup and O’Reilly Series. The big question for Stewart will be whether he can survive the carnage that usually comes with the Truck Series.

Outside of the on-track intrigue, the more compelling story might be in the garage area. Stewart’s return to NASCAR follows the leaked messages about NASCAR’s efforts to squash his short-lived SRX series. In a presser on Thursday, Stewart did not make any direct remarks about it but the tension is certainly there. If Stewart happens to cross paths with Steve O’Donnell, it could be must-see TV. Stewart is known for being hot under the collar and those messages theoretically be a sore spot still. While NASCAR does not need that drama, especially considering their good PR recently, it is something the fans would want to see.

Justin Haley

Two years after being let go due to financial reasons, Justin Haley returns to Kaulig Racing to drive one of their trucks. You have to feel for Haley a bit. Formerly one of the bright young drivers in the Cup Series, the cursed 7 car sapped all that good will and left him out of the Cup Series. However, he is still young enough to rebound, similar to what John Hunter Nemechek did after his rookie Cup season. Haley will turn 27 this season, which gives me a season or two to recoup his value. Afterall, the man did drive a Rick Ware Racing car to 2 non-superspeedway Top-10s.

However, Justin Haley has proven to be one of the better superspeedway drivers in NASCAR. Across all three series, Haley has been a reliable drafter and has won at Daytona in both the O’Reilly and Truck Series. Assumedly, the Kaulig Racing stable will continue their teamwork efforts that made them dangerous in the O’Reilly Series. Between Stewart and Haley, there is a strong chance the RAM finds victory lane in their reintroduction to NASCAR. As long as the equipment is good enough.

Anthony Alfredo

In a matter of minutes, Anthony Alfredo went from a great high in making the Daytona 500 for the third time to the crushing low of being disqualified from his Duel. Although he will not be racing on Sunday, Alfredo will be making his debut for Viking Motorsports in their second fulltime entry. Pairing with Parker Retzlaff, Viking Motorsports will have a pair of young, promising drivers who should make the most of their equipment. At Daytona, the tandem could make some noise as they have countless of Chevys to draft with.

As for Alfredo, he will certainly have a chip on shoulder after what happened last night. It would be a feel good story to see Alfredo contend for the win Saturday. While the RCR and JGR cars will likely be the favorites, you should not count out the 96 car. Aflredo has proven to be a solid O’Reilly Series racer on the superspeedways. He usually finds himself within the Top-10 for a majority of the race, especially in underfunded equipment. The key for him will be to avoid the big one(s) on Saturday. Even if he does not win, a Top-5 or 10 would go a long way to starting to heal from missing out on the Daytona 500.

Brad Keselowski

If there was going to be a season for Brad Keselowski finally win his first Daytona 500, it would be the one where he has broken leg. After slipping during a winter vacation, Keselowski fractured his right femur. It was not a certainty that he would be able to race in the Great American Race. Corey LaJoie had to fill in for him in The Clash. Meanwhile, David Ragan is on standby to replace Keselowski if he cannot continue to compete on Sunday. However, Keselowski has indicated that nothing about driving the car is currently hurting him. Rather, walking to and from pit road is causing more issues. In his younger years, Keselowski once won a race after breaking his left ankle. Can the crafty veteran do it again this year?

William Byron

No one in the history of the Daytona 500 has ever it 3 straight seasons. William Byron will look to make history this year after winning last year’s 500. What will be the best strategy for the 24 team to pull off this accomplishment? If the last year’s 500s is any indication, be running in 10th exiting Turn 2 on the final lap. With last lap cautions preventing a run to the checkered flag the past two years, Byron has greatly benefitted from the carnage around him. That is not to say that Byron is not a good superspeedway driver, as his record certainly proves he can put himself in the best position. But his two Daytona 500 wins do help sully the prestige of winning the Great American Race. If Byron is going to do it, he will have to from a backup car after getting collected in an accident in last night’s first Duel.

Critical Path Security is a cyber security firm protecting clients in the United States and the world beyond. Founded in 2017, they are as dedicated as ever to providing coverage for their clients in numerous industries. Please give them a follow (X, Facebook, LinkedIn) and thank them for their continued sponsorship of the Critical Path Security Drivers to Watch series.