Recently, it was revealed that Jesse Love, the defending O’Reilly Series champion, would be moving up to the Cup Series in 2027 with NASCAR’s most historic team! The man who’s won a championship in every NASCAR division he’s ever competed in has been linked to many Cup Series teams right at the start of the Cup season. So obviously, he’s a young talent many bigwigs in NASCAR are excited about, and for great reason.

But there’s such a thing as the right person, wrong place. And with the Wood Brothers’ recent struggles since Matt DiBenedetto left. It’s very possible that Jesse Love could be let down by the team, looking for a spark to bring the historic team back to life. Or it’s even possible vice versa, as the 2026 season presents evidence that Jesse Love either will thrive or struggle in the Cup Series.

Jesse Love’s case for Cup!

Jesse Love is an extremely talented driver who’s won in every series he’s ever been in. Jesse Love currently holds or held two very impressive NASCAR records: He’s the youngest winner in the history of the ARCA West Series, and the youngest winner ever in any NASCAR-sanctioned event, both at 15 years, 5 months, and 13 days. Beating Gray Gaulding and Todd Gilliland, although Jesse Love’s record has since been beaten. A record that hasn’t been beaten is that he is still also the youngest driver to win a NASCAR-sanctioned championship, having won the ARCA Menards Series West championship in 2020 at age 15, which is an honor he repeated the next season in the same series. And earned the 2020 Racing-Reference.info Rising Star of the Year!

He then spent two seasons in the main ARCA Menards Series, where it only took him two years to take the ARCA title, winning ten of the twenty races that season. This was enough to impress the team owner with six NASCAR Cup Series titles to his name, Richard Childress, to promote him to RCR at only 19 years old.

A move Jesse Love would quickly justify by winning pole in the first two races of 2024 and winning an impressive five poles throughout the season. And eventually getting his first career win at Talladega in only his ninth ever start. Easily winning the 2024 Xfinity Series rookie of the year. Finishing eighth in points with 18 total top tens.

Jesse Love had a very interesting start to the 2025 season that showed both his speed and his feistiness. As he opened the year, winning at Daytona, accomplishing a dream that millions have never gotten close to, at only twenty years old. Then, following it up with a pole at Atlanta, which he converted into a ninth-place finish. Then, at COTA, he would feud with the very driver he replaced at RCR, Sheldon Creed. Moving his Haas out of the way for a position that angered him greatly. And he expressed that by shoving Jesse Love into the gravel. Their war on track moved to a war of words. As Creed tweeted, “play stupid games win stupid prizes,” and Jesse Love responded, “Scoreboard buddy.”

For the rest of the season, Jesse Love has been very fast and very consistent. Winning three more poles for a total of four that season and making the final four despite not earning a single win since his opening day triumph. Not that anyone could blame him, as in the meantime, his friend Connor Zilisch was on an all-time run. Winning a record ten races throughout the 2025 Xfinity Series, including a record-tying four in a row in the summer. But when the lights came on for the finale in Phoenix, the title came down to four drivers: Jesse Love, Connor Zilisch, Justin Allgaier, and Carson Kvapil. It was Jesse Love who performed when the lights were brightest and won both the race and the championship. Though many say he stole the championship from the historically dominant Zilisch.

And they’re right, but it’s also true that in most metrics, Jesse Love was the second-best driver in the 2025 Xfinity Series season. Having the second-best average finish of all full-time drivers with 11.1. He also had the second most top tens of all the drivers, only behind Zilisch’s 23, which Jesse Love was only one behind. And Jesse Love’s 4 poles were the second most to Zilisch’s 8 poles. Which, for a 20-year-old in his second year of Xfinity, is extremely impressive and shows a lot of raw talent. Beating veterans like teammate Austin Hill and former champion Justin Allgaier.

Jesse Love hasn’t yet found victory in 2026, but is still having a great season. After the inaugural Coronado Street Course O’Reilly race. He finds himself second in points and has even earned three runner-up finishes halfway through the 2026 season. Losing to two Buschwhackers from Trackhouse Racing, those being Connor Zilisch and Ross Chastain. Cup drivers going down to the lower series are more of a problem for full-time O’Reilly and Truck Series drivers. New rules allow Cup drivers to race in the lower series more often. Making Jesse Love’s performances that much more impressive.

The Pros and Cons of bringing up a driver from O’Reilly!

So Jesse Love has the talent, but there’s a lot of risk when bringing up a driver from O’Reilly. As best seen by how Jesse Love’s friend Zilisch has been doing this season in Cup. After a historic 10-win season in NASCAR’s second tier, people did try to keep expectations realistic, considering how other champions like Ty Gibbs, Cindric, and Custer have done. But even then, Zilisch’s season has been disappointing.

After the seventeenth race of the season, Zilisch finds himself 34th in points, the second-to-last full-time driver in the standings. Only beating Cody Ware, who is on a team that’s never won a race in any of NASCAR’s national series, and is a driver who has only ever scored one top five in five years of full-time Cup racing, plus has never won a national series NASCAR race. And even more years part-time. Neither driver has scored a single top ten yet this season. Well below what people were expecting.

Now, Trackhouse co-owner Justin Marks did say Trackhouse was “rebuilding” early this season, which explains some of the lackluster results, as Spire has passed Trackhouse as the second-best Chevy team. But even then, compared to his teammates, Zilisch’s results are inexcusable. With SVG, who did win at Watkins Glen earlier this season, being in Chase contention, having gotten top 5s at the likes of COTA and Nashville. And Ross Chastain is still 12 spots ahead of Zilisch in points, being 22nd in points with multiple top fives and top tens.

Something made even worse by Corey Heim’s recent win at the inaugural San Diego race. Corey Heim had very little Xfinity/O’Reilly experience and mostly raced with TRICON Garage in Trucks. In 2025, he smashed many Truck Series records, such as most wins in a single season by one driver with 12 total wins in 2025. He claimed the Truck Series title he’d been chasing for years with a seven-wide move to take the lead in the final laps of the season finale.

But even after making history, Heim couldn’t find a full-time ride anywhere in 2026 due to a lack of sponsorship and for staying loyal to Toyota despite its fewer teams than Ford and Chevy. But did get 12 total Cup races with 23XI Racing, one of the Next Gen’s most successful teams, to show if he’s ready for the Cup. A question he answered with an emphatic yes when, a few weeks after it was announced he’d be full-time for the team in 2027. He, in only his 13th ever Cup start, would in the inaugural Coronado Street Course race beat many Cup and road racing veterans alike, dueling with his own points-leading teammate Tyler Reddick to claim his first Cup Series win.

Heim is far from the only driver who came up to Cup from trucks and found early success in the Next Gen era. Hocevar is the best example, being another driver who’s compared to Dale Sr a lot, but for his time in Cup. This started when he replaced fellow rookie Noah Gragson in the Legacy No.42 and immediately outperformed him. Despite Gragson having a lot more wins in Xfinity than Hocevar did in Trucks.

Hocevar nearly made the playoffs and came close to getting his first career win a few times in his first full Cup season with Spire. He has won his first career Cup Series race this season at Talladega and is currently ninth in the Cup Series standings after San Diego, well inside qualifying for the 16-driver Chase. Todd Gilliland and Zane Smith, two of the Front Row drivers, also came straight from Trucks into Cup. Their performances have earned much praise from the Cup Series garage. And Zane Smith was a car length away from earning his first career win in the Cup Series in his rookie year, losing to three-time Cup Series champion Logano at Nashville.

This is a surprise to many and has even created a narrative that younger drivers need time to get used to the Next Gen, a narrative Heim might’ve shattered in NASCAR’s first-ever race in San Diego. But it isn’t a surprise to anyone who knows the cars. As there are reasons why drivers from NASCAR’s third-tier trucks are transitioning to Cup better than drivers from NASCAR’s second tier, O’Reilly.

Now, the Cup cars’ additional 5 inches in their wheelbase might not seem like a massive difference, but to the drivers, it is. By extending it from the Xfinity Series’ length of 105 inches to 110 inches, the ripple effect results in a car that feels totally different. From the aerodynamic packages to the safety modifications, piling on challenges for young drivers trying to adapt.

The difference doesn’t stop there in the Xfinity Series; cars are approximately 11 inches longer, one inch taller, and four inches narrower than Cup Series competition vehicles. With its larger overall size, the Cup Series Next-Gen car weighs in, with a driver, at 3,500 pounds, compared to the vehicle used in the Xfinity Series, which is 100 pounds less!

Then there are the similarities the trucks have to the Next Gen cars, which someone like Jesse Love, who’s only ever done four truck series starts, won’t have a chance to learn. Both Cup cars and Truck series trucks are purpose-built tubular steel race chassis. While they mimic production consumer vehicles (like the Ford F-150 or Chevrolet Silverado in the Truck Series, and the Toyota Camry or Ford Mustang in the Cup Series), underneath the sheet metal, the chassis and aerodynamic shapes are fundamentally constrained by NASCAR’s regulations. Both vehicles use identical Xtrac 5-speed sequential transaxles. The removal of the traditional four-speed manual from behind the engine has unified the shifting mechanics and gearbox operation across both series. And the same digital dash and steering wheel electronics layout. Not to mention similar aero packages to the Cup Series, or at least much more similar than the O’Reilly Series aero package.

So, as for his rookie season, things are definitely looking bleak, considering he’ll be 22 years old coming to Cup from O’Reilly, especially since Wood Brothers Racing is still less competitive than Trackhouse this season. The Wood Brothers’ only driver, Josh Berry, another driver who came from the then Xfinity Series into Cup, is currently 30th in points. So short-term, it’s looking ugly for Jesse Love, but long-term, there’s hope that with a patient team, his raw talent could still help him blossom into a superstar.

Ty Gibbs’s career path is very similar to Jesse Love’s and even more so to Connor Zilisch’s. Ty Gibbs was an ARCA champion at only 18 years old and, at the same age, went part-time in the then-Xfinity Series. Winning in his debut at the Daytona road course. He won four races in his part-time campaign, then went full-time the very next season, in which he won eight races and the 2022 Xfinity Series title.

His rapid rise through the ranks, with his constant winning at a ridiculously young age, and his ability to anger other drivers with his aggressive driving, had many comparing him to the likes of Dale Earnhardt Sr. But his few seasons in the Cup were far from the intimidators in terms of results. While Dale Sr won a Cup Series title in his second full-time season in 1980. The only accomplishments Ty Gibbs had completed were winning the 2023 Cup Series ROTY and making the Playoffs for the first time. He was eliminated in the first round and finished 15th in the standings. Ending the year having gone two and a half seasons without a victory in the Cup Series.

Something that continued into 2025, a season where he won the first-ever NASCAR in-season tournament, but also broke a JGR record once held by JJ Yeley for most starts without a win at one of NASCAR’s most successful teams. And after 2025, many fans were beginning to consider him a bust and only had the seat because he’s the grandson of the team owner.

2026 proved that raw talent hadn’t disappeared, however. At the start of the year, Ty finally got the monkey off his back and won his first career race at Bristol in the spring. And while it’s his only win so far this season, it’s far from his only great performance. As he sits 5th in the points after the 17th race of the season, he has spent most of the year in the top 5 in points. Beating out many of his veteran and race-winning teammates like Christopher Bell and Chase Briscoe.

Another former Xfinity champion, Austin Cindric, has had slower improvement, but it’s evident he’s learning this Next Gen and is getting better. With four top tens and one top five this season, it’s been the steady consistency that finds him in the Chase, being 15th in the standings after the Anduril 250. He has been inside the Chase for the majority of the season, in a major change of fortunes for the driver of the Penske No.2.

Who has won three Cup races, including the 2022 Daytona 500. But has always consistently lagged behind his more experienced Penske teammates like Blaney and Logano. But this year, Cindric is currently averaging his best finish since his historic rookie year, where he won the Daytona 500, and is three spots ahead of his championship-winning and fellow Daytona 500-winning teammate, Joey Logano, who finds himself 18th in points after San Diego.

So if Wood Brothers is patient enough, Jesse Love could blossom into the superstar 2023 Cup Series champion, like Ryan Blaney was for WBR when he was driving the No.21 in the late 2010s. Who led them to their first-ever postseason entry in 2017? But will the Wood Brothers be so patient with Jesse Love? Comparing him to both Ty Gibbs and Austin Cindric, something to keep in mind is that those two have family ties with their teams. Ty Gibbs is the grandson of the team founder and owner, Joe Gibbs, and Tim Cindric, Austin Cindric’s dad, is a higher-up in Penske’s IndyCar branch. While Jesse Love has no blood ties to the Wood Brothers.

How long a leash will the Wood Brothers give Jesse Love?

In the middle of the 2010s, the Wood Brothers had a turning point. For years, NASCAR’s most historic team struggled to win only one race during the 2000s and had been relegated to a part-time team on the verge of shutting down. Trevor Bayne winning the 2011 Daytona 500 in his second Cup Series start changed everything for the No.21. Helping them find the money to be full-time again.

Then, a partnership with the Team Penske dynasty not only gave them better equipment but also landed them a rising young star by the name of Ryan Blaney. Who helped the team rebuild from DNQing from races in 2014 to winning the race at Pocono, clinching a spot in the 2017 playoffs!

The team hit a slight lull after Blaney moved the mothership to drive the Team Penske No.12, where he’s done all his Cup Series driving ever since. And Paul Menard took over in the No.21, bringing his Menards sponsorship with him. But after Menard retired from the Cup Series, the Wood Brothers were able to snatch, at the time, the rising Cup Series star Matt DiBenedetto and immediately returned to the playoffs in their first season as partners. And they were a Daytona wreck away from repeating the honor in 2021.

But sponsorship money is always important to keep a team running, and DiBenedetto lacks such funds. They turned to Harrison Burton, whom they signed to drive the No.21 in 2022. He brought with him sponsorship from Dex Imaging on the strength of his family name and the eight career Xfinity wins he earned with Joe Gibbs, where he was a contender to win most weeks.

But like many of the Xfinity drivers we discussed, Burton struggled to adapt to the brand-new Next Gen, failing to adapt his driving style to all of the technical changes and challenges the Next Gen brought. Bringing the Wood Brothers their 100th ever win was a great highlight, but the sole highlight in an era that saw the No.21 return to the back of the field time after time. The Wood Brothers’ average finish sharply declined from 16.9 during DiBenedetto’s last season to never coming with an average finish of 20.9 during Burton’s team in the No.21 Ford. Matt has had three top fives during both of his seasons with WBR to Burton, only having two total in his three seasons with the team.

After 2024, Burton and Wood Brothers split, returning to the second tier of NASCAR, while the No.21 team searched for another star driver. And seemingly found in former SHR and JRM driver Josh Berry. Like Burton, Josh Berry had found a lot of success in the Xfinity Series with Dale Jr’s team. Winning five races and, unlike Burton, having made the final four in 2023. He was also much more experienced, being 34 years old when he signed with the team, having done years of late model racing before impressing many in 2021 with a part-time stint for JRM. He looked like a promising Cup driver in 2023 when he did 10 races, mostly subbing for other drivers, and earned three top tens, including a runner-up finish in Richmond.

In Berry’s rookie year, he finished 27th in the standings, but it’s something that could be easily forgiven. As his first full year in Cup was Stewart-Haas Racing’s last year as an organization, the lack of leadership in the team’s final years had become widely known. So with a year of experience under his belt with a more stable team, not on the verge of death. It was assumed he would do much better.

And he did, he won his first-ever Cup race in his third start with the team at Las Vegas. And he earned three top fives and eight top tens during the 2025 season, numbers WBR hadn’t seen in the DiBenedetto era, and earned a playoff berth. The duo was seemingly building something stable together, and the future once again seemed bright.

Then, not even halfway through the 2026 season, it was announced that Josh Berry would not be continuing to drive for the Wood Brothers in 2027, and quickly afterward. The news that Jesse Love would be Josh Berry’s replacement on social media. It has not been a good season for Berry and the No.21 crew. Currently, finding themselves 30th in the standings, with only two top-10 finishes so far in 2026. The Wood Brothers’ struggles fall perfectly in line with Ford’s in 2026. The blue oval has only had a single win during the first 17 races of 2026.

Ford’s current approach to NASCAR is another factor as to why the Wood Brothers have been struggling since the Next Gen era began. In the lawsuit that FRM and 23XI filed against NASCAR, it was revealed that “A-tier” Ford teams receive only $1 million in manufacturer support from Ford. And Wood Brothers is not an A-tier team, so who knows how little they get. Though they do get support from an A-tier team in Penske, this is sure to limit the support they can get from the multi-time NASCAR champions.

But Penske is also going through its own struggles at the moment. Ryan Blaney, being third in points and grabbing Ford’s only win so far this season, only does so much to cover the cracks being exposed by their other two cars. With Cindric barely in the Chase with only four top tens. And three-time Cup champion Logano has been out of the Chase for a lot of the first half of the season. Walking away from San Diego, 18th in points.

And looking at Roger Penske’s other racing operations, you’ll see a similar pattern. Last year in IndyCar, the place where Penske made its name and, for most of its history, was either the fastest or second-fastest team in the series, with only Ganassi challenging its crown, especially after Andretti went through its own struggles to start the 2020s. But in 2025, Penske’s IndyCar team wasn’t fast at all. With their three drivers finishing 9th, 10th, and 12th in the standings, respectively, and not getting a single win all year. A year that saw their most tenured driver, Will Power, leave for Andretti, who had a driver finish second in that year’s points. 2026 has been better for them, with them having two wins ten races into the season. And new driver Malukas is second in points after Road America. But the fact that no other driver in the top five in points shows how teams like McLaren, Andretti, and even Meyer Shank have been able to catch up to the once-juggernaut of the series.

But at least Penske’s NASCAR and IndyCar teams are still around; that’s more than can be said for Penske’s world endurance championship effort with Porsche. When they made a shock exit from a series currently in a golden era, and after Penske and Porsche won two races in 2025 and finished third in the team’s championship.

Though they did stay in the American-based IMSA series, they currently find themselves second and fourth in the Manufacturers Championship after winning their first two races of the season. Though they haven’t found a single podium in the four races since, which is a downturn in form from their championship-winning season in 2025. Something you wouldn’t expect after they left a more expensive series, and could put some of those resources towards their North American efforts.

In 2020, Penske took over both IndyCar and the iconic Indianapolis Motor Speedway, almost a decade after Penske agreed to an alliance with Jesse Love’s new team, the Wood Brothers. And ever since then, Chip Ganassi has dominated, winning every single title with Palou and Dixon, with the lone exception of Will Power with Penske in 2022. And Penske’s three NASCAR Cup Series teams finished with average finishes of 13.7, 12.9, and 10.8 by the end of 2019. To have his three Cup cars average 14.6, 15.3, and 20.9 by the end of 2025.

Most team owners stick to one series or one motorsport; it’s rare for a Roger Penske type who operates multiple teams in multiple disciplines and does so as successfully as the billionaire from Ohio has. But now, running the most historic track in all of motorsports and one of the biggest racing series in the world, in IndyCar, has proven detrimental to his racing operations. And the Wood Brothers, who relied on Penske’s equipment being seen as an extension of their NASCAR operation. It is now a bystander to both Penske’s lack of focus on its motorsport operations and Ford’s lessened interest in NASCAR.

This’ll put even more pressure on Jesse Love to get results as soon as he straps into the No.21. Proven by Josh Berry being kicked from the team after a terrible playoff round and a bad half a season, ignoring the initial promise 2025 had. Part of that could be Berry’s age, being a man in his mid-30s, so Jesse Love will likely be given a leash more similar to the three seasons Harrison Burton had in the No.21. But if they’re kicking Berry because of his age, part of that is that they see a higher ceiling with Jesse Love. This would put more pressure on the young driver.

But if he is given a longer leash with his raw talent, he could see improvements like Ty Gibbs and Austin Cindric have and have a good start to life in the Cup Series. Love has the talent to become what Wood Brothers needs, but the window for patience may be shorter than what his development curve requires, and that timing mismatch is the real risk. Thanks a bunch for reading!

Image Credit: Patrick Vallely