[2] Born in Hartford and grew up in East Granby, Simmons began his professional career in the Barber Dodge Pro Series in 1998.

The "Career Enhancement Award" of $250,000 that went with the title was not enough to secure him a ride at the next level, Indy Lights, so he returned to Barber Dodge in 1999.

In 2004, Simmons once again lacked the sponsorship needed for a full-time ride, However, AJ Foyt put him in his Infiniti Pro Series car at Indianapolis where the finished 2nd.

That led to Mo Nunn giving him a chance to qualify his second car for the Indianapolis 500, which he did, with just 37 laps ever in an IndyCar, and finished 16th in the race.

His best finish in 2006 was 7th place at Nashville Superspeedway and Infineon Raceway.For the 2007 season, Simmons was joined at Rahal Letterman by IRL veteran Scott Sharp.

He was given a chance to return to the IndyCar Series, albeit temporarily, to drive a second entry for A. J. Foyt Enterprises in the 2008 Indianapolis 500 and qualified 24th.