#6 Robby Gordon.
A lot of the drivers on this list will have a relatively short Cup series career, but Robby Gordon will stand as the exception to that rule. Gordon started racing part time in The Cup Series in 1991 and wouldn’t even win his first race until the year 2001 at Loudon New Hampshire. Gordon parlayed that success into a multiyear deal with RCR and Caterpillar, but has seemingly struggled since then.
While Gordon was known as a controversial driver due to his aggression on the track, he was also known for being very hit or miss throughout the season when it came to finishing. In fact, Gordon only managed three wins, nine top-five’s and 19 top-ten’s during his time with RCR at the Cup level, which was pretty good, but not what others expected of him.
Unfortunately for Gordon, he announced that he would be leaving RCR at the end of the 2004 season due to performance issues and would start his own Cup Series team instead. RCR originally didn’t want to let him out of the remainder of his multi car deal, but Gordon was later let go when Jeff Burton became a free agent later in the year.
In the end, while Gordon did have some success with his own team, especially since he managed five top-five’s, and 12 top-ten’s over the course of eight season, he probably would have achieved so much more if he would have stayed with RCR. Maybe Gordon could have even waited for free agency when his contract was up and waited to go to an even better team instead.