When Dale Jr. left DEI he wanted to keep the number 8. His stepmother and DEI owner Teresa Earnhardt would not allow him to take the number to Hendrick Motorsports. Therefore, Junior was left to choose from other available numbers. He then chose number 88.
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Dale Earnhardt Jr. didn't really chose the number 88 for his car, NASCAR gave it to him as his number.
Dale Jr. wanted to keep the number 8, but his stepmother Teresa Earnhardt would not release the number to him. Dale did have about 2 or 3 other numbers he could have chosen, examples: 81 and 83, which he drove in the Nationwide series, but decided on the 88.
Dale Sr. had several car numbers during his Cup Series career, including the #2 and #15. But he is most remembered for driving the black #3 GM Goodwrench car.
Dale also drove the #3 car with Wrangler Jeans sponsorship earlier in his career.
Because it's his favorite number!! Well it's his dads......favorite number
He chose 88 because it is the double 8.
He chose that number so that all the fans out there who got tattoos of the number 8 wouldn't have a hard time changing it to another number. This way all they have to do is add another 8.