Technical alliances are NASCAR’s open secret. Smaller teams lean on the big players to survive, using their cars, tech, and brainpower just to stay in the fight. In 2024, we saw the grid shift when Front Row Motorsports ditched RFK Racing to join Team Penske’s circle alongside the Wood Brothers. These deals can make or break a team. Look at Denny Hamlin- co-owned 23XI Racing’s securing a championship 4 appearance in 2024, thanks to the team Hamlin drives for, Joe Gibbs Racing. However, these alliances can also keep a team in the dark, stuck as a shadow to the powerhouse they’re tied to.

Something feels off with the No. 21 Wood Brothers car, which is confusing. It’s early 2025, and Josh Berry’s driving it like it was made for Team Penske, not the weaker car we’re used to Harrison Burton driving when WBR remained a perennial bottom 20 team. At Phoenix, he finished fourth, right up there with the leaders. At Las Vegas, he collected stage points and after smart pit-stops, he rocketed to the lead. This isn’t the No. 21 we’ve seen for years, lagging behind Penske’s other superstars. Denny Hamlin might have the answers to all the questions after this sudden rise of Berry.

Deny Hamlin feels guilty about taking Josh Berry for granted

Let’s go back. Since 2015, the Wood Brothers and Penske have been partners. WBR owns the charter, but the car comes from Penske’s shop. It’s mostly Penske people working on it—Penske crew, Penske tech, Penske everything. We’ve seen drivers like Ryan Blaney use the No. 21 to good effect, winning at Pocono in 2017 before moving to Penske’s No. 12. After that, it’s been tough.

Paul Menard, Matt DiBenedetto, and Harrison Burton, all drove it, but it rarely stood out. Burton won at Daytona last year, but that was more about timing than speed. In most races, it couldn’t touch Penske’s top cars. We all thought it was just a test car for Penske’s real stars. However, Hamlin shed light on the narratives surrounding #21 that shed light onto diverse narratives surrounding the team.

Denny Hamlin said on his Actions Detrimental podcast, “Wood Brothers own the Charter but I don’t know that the employees like if you ever see them at the racetrack they’re all Penske employees people that we know that are Penske employees. But we’re all guilty at times of when things typically have been bad for the 21 car we just say ‘It’s Penske’s development team they’re only gonna be but so good’… ‘They’re just priming people for their house cars’… ‘It’s a deal that they cut with the Wood brothers to run that car out of their shop and you know help them out’.”

So what’s going on? Josh Berry has been solid as he’s won in the Xfinity Series under Dale Earnhardt Jr.’s mentorship. Another theory that comes to mind is that maybe Penske might’ve changed something. They put Miles Stanley, a former Penske engineer who’s helped win titles, as crew chief. That’s a big deal. Maybe they’re giving the No. 21 more help now, treating it like a real Penske car instead of an experiment.

Denny Hamlin came clean, “When things are good, we’re definitely quick to give Penske the credit, right? … I’m guilty of thinking that as well a kind of wondering and scratching your head yeah but if it’s even if it’s you know, just a straight a– development team of Penske, which I don’t know to be true. How could they be so far off for so many years, like way off of, you know, the worst Penske car, whoever that is, right, on any given weekend? And now it looks like it’s just us, it’s just one of the boys. It’s just one of the cars that come out of that shop that’s just like the 2 and the 12 and the 22, and it’s got the speed that they’ve got.”

Hamlin’s comments are reflected in Berry’s performances in his Ford Mustang, as compared to the Penske faction. Joey Logano, the Penske #22 and three-time Cup Series Champion is yet to notch a top-5 finish this season, while Berry already has two, along with a win! Ryan Blaney, who had been Penske’s most consistent driver so far with two top-10s and one top-5 is also yet to post a win.

The #21 WBR team used to be nowhere near competing with these guys at Penske. From 2018 to 2024, the #21 car had just 1 win and 9 top-5 finishes to its name. So far, they’ve already equaled that win tally and led more laps in 2025 than the last two years combined! Hamlin recalled his realization of this significant improvement. “I noticed it in practice in Phoenix. Wow, the #21 car is good,” he added. Berry notched up his first top-5 of the season in that race.

We’re not sure yet about Josh Berry’s sudden turnaround. No one is. When it’s bad, we say Penske doesn’t care about it when good, we say it’s all Penske. Either way, we have to keep an eye on this because this turnaround feels off and a lot of questions need to be answered. While Hamlin pokes around the nitty-gritty of team alliances, his own team recently made big moves in Vegas, while he enjoyed his time following in Michael Jordan’s footsteps.

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Denny Hamlin leaves Vegas with a lot of money and possibly a new sponsor

Denny Hamlin’s weekend in Vegas was a total whirlwind with extreme highs and some real lows. Friday night, he’s at the slots, just messing around, and boom, he nails a $126,150 jackpot. He’s leaping out of his seat, hollering, totally floored. Then Saturday, he’s back at it, raking in another $85,825, pushing him over $200,000, as he posted on Instagram with a wry smile. Well, credit needs to go to Michael Jordan here. The 23XI Racing co-owner and 6-time NBA Champion once said, “I don’t have a gambling problem. I enjoy gambling.” And it seems like this mentality has rubbed off on Hamlin! However, come Sunday, Hamlin’s emotions took a 180-degree turn.

At Las Vegas Motor Speedway, he was pushing his No. 11 Toyota hard until a pit road speeding penalty knocked him to the back. That one hurt. He battled back but landed in 25th. After all that casino luck, you’d hope for a better finish. Still, he’s sitting 12th in the Cup standings, so he’s not down for the count. The guy’s a fighter. However, off the track, it’s been brutal for most of the season, until JGR recently showed a sliver of hope.

FedEx, his sponsor for 19 years since 2005, pulled out after backing 13 races in 2024. Then Mavis Tires and Brakes, who jumped in for eight races last year, bailed too. That’s two big hits. Hamlin’s been real about it—at the 2025 Cook Out Clash, he said, “Is it concerning from my end? Maybe a little bit, but it’s probably more concerning from JGR’s standpoint.” You can hear the worry in his voice, and it’s tough not to feel for him.

But here’s some hope: Joe Gibbs Racing might have a lifeline. Word from Adam Stern at Sports Business Journal is that Progressive Insurance could step in as a primary sponsor for 2025. It’s not locked yet, but JGR’s in the running. Progressive hasn’t backed a car since Ryan Newman’s two races in 2020, so this could be big. Alongside them, JGR lined up National Debt Relief, King’s Hawaiian, and AMPM to join returning sponsors SportClips and Yahoo. Hamlin is 21 years in NASCAR, and he’s still grinding.  It looks like his journey at JGR isn’t coming to an end just yet.