4. James Stewart
2007 & 2009 AMA 450cc (Premier Class) Supercross Champion
2006 FIM 450cc (Premier Class) World Supercross Champion
Premier-Class Wins: 50
Most Premier-Class Wins in a Season: 13 (2007)
It’s not an exaggeration to say that James Stewart is the most exciting racer in the history of motocross and supercross racing.
Stewart turned 16 years old only weeks before his first-ever 125cc supercross in Anaheim in 2002, where he finished second after a couple of falls. From that point in 2002 until only a few years ago, Stewart had never lost a supercross main event in which he didn’t fall at least once.
Stewart holds the record for the most career wins in the 125/250cc regional SX series with 18, and any time he’s on a motorcycle, he’s a threat to win. The only reason he’s ranked number four on the list is because the crashes and injuries have left him with only two AMA championships (and one FIM championship in 2006, back when points were kept separate between the simultaneous AMA and FIM championships-Stewart won the FIM title that year but lost the AMA title by two points to Ricky Carmichael).
Just like Bradshaw did starting in 1989, Stewart fundamentally changed the sport, revolutionizing riding techniques and styles as well as motorcycle setups at the top level. If he never races again, Stewart should be remembered as one of the most revolutionary racers in history, and if one or two things would’ve gone differently for him, it’s easy to imagine him being the greatest in the history of the sport.