Simon is the middle son of DGI board of Directors member Dominick and his wife Crystal Rutherford. He grew up close friends with the Devonshire family and Lowell is his godfather, he knew from a young age that he was different than most boys he hung around. Always smart and a bit cunning it was something that played into his career as he grew under Lowell. He has always been close to Jackson and they had a bit of a kindred spirit between them, he was always in his older brother Julian’s shadow. He and Zach began a high school relationship and when Jackson caught them at a party it was out that he preferred men to his friends. In high school he came out to his father his wanting men and for that Dominick didn’t speak to him for a few years. He was at the party that killed Catherine Scottson during college and he can safely say that is when his life changed. Most of their group were horrified when Cat and Jackson were both high and Cat died in a horrific car crash. Most of them stopped the drugs, he was one of them others went down that path like Jackson. Cat’s death began to haunt him, seeing how he was the one that got the drugs that night throughout college and he went and got his bachelors in business.

He and Mason finally gave into their desires for each other one night after he completed his masters and they have been lovers ever since. He does still venture to Club XES every now and then to engage in the activities that Philip’s club offers like access to a hit now and then, the beautiful women or men but for the most part he has stopped the partying. Lowell also made him a full time employee at DGI where he runs much of Lowell’s business dealings and he works heavily with Selina and Dani. He sought Dani out after she came home in order to make her replace him as the head of PR at DGI so that he could take over more of the duties that Lowell has asked him to do. While he is happy to remain friends with the Devonshire’s and still have his friendship with both Jackson, Hunter and Mason he also is haunted by the things that Lowell has his him doing in the name of DGI. He has been Mason’s lover for the past few years and while he loves Mason and can see a life with Mason he is tired of hiding in the closet as Mason’s dirty secret. He knows Mason has a lot riding on his sexuality remaining a secret he however is ready for the world to know about them no matter the cost to Mason.

Season 1

Simon started the season thrilled his best friend was back from rehab going as far as to arrange with Talia Jackson to meet Dani and exchanging twenty dollars when the two left together. He also dipped his hands into DGI affairs when needed and Lowell asked him to, work life was amazing. His home life however he was frustrated after being in a secret and hidden relationship with Mason for years, he was growing tired of lying to everyone and keeping the secret. He told Mason as much at Selina’s botched wedding and asked for space from their relationship. When Jackson relapsed he encouraged his friend to be a better person and pointed out he had changed since getting with Dani for the better. When he was called to La Callie he was floored when Tony played a recording of him and Mason from Selina’s wedding. Mason accused him of releasing the tape and Simon dumped him in return. He also had to help navigate Lowell’s business plans with Ronan Madden where he negotiated Ronan turning a blind eye to Jamal and Jackson in return for a lucrative casino deal.

Season 2

Simon would have a intense new relationship with Jamal’s recording artist Ivan “IMoney” Castillo. Ivan refused to come out and would explain the hip-hop lifestyle doesn’t support gays. Simon was reluctant to get back into another secret relationship after everything that happened with Mason but eventually he gave into his desires. He quickly learned that Ivan had his own way of doing things when Ivan attacked Rory on the roof of Club Vertigo and instead Jamal fell and Rory lied to protect Ivan. Simon told Ivan that there was nothing he wouldn’t do for the Devonshire’s and his feud with Rory over everything that happened with Kendrick was over or they were, Ivan reluctantly agreed. He was also furious when Ivan showed up to Jackson and Dani’s wedding with a gun only for them both to be pulled into helping dispose of Dimitri’s body.