Jonathan was born and raised in Detroit, Michigan. He was born into an Irish-American family to mother Caitlin and father Brian.

Jonathan moved to Los Santos in the early eighties where he built a relationship with a known criminal mob that ran specific areas around the city. As years went on, he grew more and more respect for himself around the city and was rewarded for his efforts with a crew. A crew meant he had to work less, yet earn more money from having guys under him known as run-arounds which would do the dirty work he once had to do to earn money. By the mid nineties, Jonathan was running a fully operational crew that was raking in a large amount of money, but money brings attention and that attention being the authorities. Jonathan was arrested in 1995 for allegedly distributing large amounts of narcotic substances said by an unknown source, but, was later released due to lack of evidence.

Jonathan's superiors summoned him and sat him down for a meeting and informed him that he would be running a trucking industry, giving Jonathan more responsibilities. As time passed Jonathan had more and more truckers on his pay-roll which were being taxed to pass and operate in Montgomery. Gradually innocent truckers and members of the mob were also forced and told to smuggle certain substances and goods through the city, enhancing the amount of narcotic and firearm distribution within the city.

Jonathan also knew a cop called Daniel, and he too was on Jonathan's pay-roll and would let him know if anyone in his crew was arrested and spoke about things they shouldn’t. He received a phone call from Daniel telling him they needed to meet and how it was urgent. Jonathan got in his SUV and took a long drive to a boarded up abandoned building where he was greeted by Daniel and a plastic folder that he was holding. They sat down and Daniel began to tell Jonathan that four of his crew members were pulled in by the police for driving whilst under the influence of drugs and having a trunk full of weapons and ammunition. The police struck a deal with the mobsters stating that they would walk free if they were to give information on Jonathan's operation or were guaranteed to spend a large prison sentence, and they agreed. Jonathan stood up calmly and strolled out of the building and sat in his SUV quietly, trying to get over what he had just been told. After sleeping on numerous thoughts, he made the decision to take them all out and them being drug addicts, they wasn’t hard to track down.  Once things had blew over, he called up his old friend Francis to bring him up to date.