Both men were, and are great drivers. Since Dale died in 2001, it would really be hard to say. If you were talking about Dale Jr., he's a good driver, but not in the league with Gordon, an all time great.
Jeff Gordon is better because he won more races than Dale Sr.
In my opinion, Dale Earnhardt is better.
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Dale Sr. and Darrell Waltrip were friends off the track and rivals on it. Darrell Waltrip expressed his dislike towards Dale Sr. when racing him, being a bully etc. Off the track he explained how Dale was truly a good person. Showing it was all business, nothing personal.
Actually, they were friends. Dale always respected Jeff's abilities, and said once he was the future of Nascar. Jeff, on the other hand, said he learned more from Dale than any other driver.
No, they were not. Jeff Gordon has driven for Hendrick Motorsports his whole career. Dale Earnhardt Sr. drove for Richard Childress Racing during that span.