In 1987 he attracted what is believed to have been the biggest fee for an amateur Rugby League player to turn professional when he signed for Halifax for £80,000.
But an attempt to smash another record in a gruelling endurance challenge landed the 34-year-old in hospital.
Simon was aiming to break the Guinness World Record physical fitness challenge.
But he was forced to give up the feat with the finish in sight after medics advised him his health was in danger.
Monitored
Simon was rushed to hospital suffering from severe dehydration about 17 hours into the challenge and had to stay overnight while doctors monitored him.
Although thwarted, he has still raised about £7,000 for charity.
And, vowing not to be beaten, he says he will make another attempt to claim the title when he has fully recovered.
Today Simon, of Pontefract, said he was disappointed, but doctors had since told him if he had carried on last Saturday, he would have suffered permanent damage.
"Even though my mind was willing, my body could not get through it," he said.
"My actual kidneys had taken such a beating, I had to stay in hospital and have quite a few blood tests."
But he said he had not ruled out attempting the marathon feat again.
"If I can get some companies to sponsor me, I would be prepared to challenge the current world record holder head-to-head."
The personal trainer started with a 20-mile swim at a private pool, went on to Fitness Base gym in Pontefract and ended at Xscape in Castleford.
During the challenge he cycled, ran, hiked, rowed, lifted weights and did exercises.
After eight hours, cramp set in and he was treated by a physiotherapist.
When he was forced to give up he was on target to beat Texan Rob Powell's world record of 19 hours, 17 minutes and 38 seconds.
Father-of-two Simon was raising cash for Yorkshire Cancer Research and the Sports Trust Fund, a new charity he is setting up to help children become more involved in sport.
He said many were prevented from progressing because of a lack of cash and he wanted to help them reach their full sporting potential.
Prepared
Simon was keen to raise money for cancer research because his mum, Elaine, died from the disease 11 years ago, at the age of 43.
He had prepared for six months for the challenge and thanked everyone who had supported him.
"Without my family and friends I would not have been able to do this," he said.
He has also vowed to continue raising funds - though in a less energetic way - by holding a charity ball in February on behalf of the same two causes.
Simon appealed for support from local businesses and individuals.
E-mail him at simon@bodydesign121.com to help, or for more information.
katie.baldwin@ypn.co.uk