With three generations of exceptional racing legacy, the name Earnhardt is as popular as NASCAR itself.

While the Earnhardts are primarily known for dominating the track from behind the wheel, the family has also seen its fair share of success in team ownership. Dale Earnhardt Sr.’s DEI saw a fair bit of success and may have likely become one of the biggest names in NASCAR before it ceased operations for multiple reasons.

Dale Earnhardt Jr., too, has seen incredible success as a team owner alongside her sister, Kelley Earnhardt. However, most of the team’s success has come in NASCAR’s tier-two series, and over the years, there have been several questions about JR Motorsport’s entry in the Cup Series. Recently, a NASCAR insider pointed out a roadblock that might be standing in the way of Earnhardt’s aspirations.

Does NASCAR Have Room for More Charters?

When NASCAR journalist Bob Pockrass sat down with Kevin Harvick, the duo dissected several elements of the current season. These included the playoff situation and NASCAR’s ongoing lawsuit with 23XI Racing and Front Row Motorsports.

In connection with this, Harvick mentioned the current charter situation in NASCAR and the arrival of RAM as an OEM in the upcoming season. The former driver also wondered if the landscape opened the door for more cars on the track in the sport.

Pockrass responded by highlighting that NASCAR had the ability to issue 40 charters. As the two rambled about what NASCAR could potentially do with the new charters, given the gaps in the current clauses, they believed the decision lay solely in NASCAR’s hands.

One Entry Condition Stands in the Way of Dale Earnhardt Jr.’s Road to the Cup Series

The possibility of extra charters also led Harvick to wonder if Earnhardt’s JR Motorsports could end up with one. The 2014 championship winner also claimed, “There’s nothing better for Cup racing than the Earnhardt family owning a Cup car.”

As Pockrass admitted that the possibility of JR Motorsports landing a Cup charter was open, Harvick revealed what he would do if he were the boss of NASCAR. The 49-year-old said, “If I were NASCAR and Jim France, I would give Dale Jr. whatever he wanted.”

While Pockrass revealed the willingness of JR Motorsports to want a Cup charter, he also highlighted that the organization had considered making a move for it on several occasions but ultimately decided to proceed on a specific condition. Pockrass noted:

“They want to run that program year-to-year without losing money. They don’t want to look at the charter as something like, ‘Okay, this is something on which we can lose $20 million over 10 years, but then make it back when we sell the charter.’ They’re not looking at it that way.”

He also pointed out that the team would require sponsorship and funding to run a car in the Cup Series.

Earnhardt may not have trouble landing sponsorships and funding if he enters the Cup Series. However, with the team’s entry conditions, it remains to be seen if an Earnhardt family car will make it to NASCAR’s top tier anytime soon.