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James has three children: a daughter and a son with his first wife, Karla James, to whom he was married from 1991 to 2002; and a daughter with his second wife, stripper/adult actress/producer Janine Lindemulder, to whom he was married from 2002 to 2004.In October 2009 James's ex-wife Lindemulder, who had been in federal prison for six months for tax evasion, sought to regain custody of her then five-year-old daughter with James—Sunny—after James had been granted sole guardianship of her.James said the CARB refused his offer to recall and modify the uncompliant choppers.Since 2005 West Coast Choppers has built emissions-compliant choppers.The 1950s style hamburger stand—named after his beloved pit bull who is now deceased—featured Angus beef burgers, low-fat burritos, organic vegetables, and biodegradable wrappings. James also had partial ownership in Austin Speed Shop in Austin, Texas which he left in 2013 to focus on the re-opening of West Coast Choppers in Austin.Other business ventures include the Chopperdogs fan club and the Jesse's Girl clothing line.
He asked the Red Jacket Firearms team to build a customized Browning Automatic Rifle for him, and even assisted in the build himself. (representing Orange County Choppers), with Gas Monkey Garage (featured on the Discovery series Fast N' Loud) entering the competition in 2012.
Following the success of the documentary, the Discovery Channel approached James with an offer to host a new show called Monster Garage where James and a crew of mechanics modified vehicles under a short deadline.
James later established Payupsucker Productions, under which he produced shows like History of the Chopper, Iraq Confidential with Jesse James and Green Scream, in which James plans to break the land speed record with an eco-friendly hydrogen car.
James sought to retain full guardianship, citing fear of the environment in which his daughter would be placed if returned to Lindemulder.
In March 2010 a media scandal arose when several women claimed to have had affairs with James during his marriage to Bullock.
Through James's show "History Of The Chopper" there are also glimpses of his involvement with the Hells Angels.