Being the only son of two bright corporate employees, he was required to study hard, and so sharpened his mind, but when a corporate war broke out and one of the battlefields was his parents' company, he lost his family, without even so much as a body to bury or mourn. After a short stint trying to make it as a minor league baseball player, he was taken in by a local punk gang, and quickly rose through the ranks. He learned to rely upon his brains and his charm, and let others do the fighting. This was reinforced by the feeling he got every time he had to kill someone, and soon he was sickened by the fact that he was calling in hits on people that could be just like him, only in the wrong place at the wrong time. One day, a target of his surveillance was one of his childhood friends, and so instead of following through with his duty, he ran. When the gang cought up to him, they took both his eyes in a brutal warning to those who step out of line. He is now on the gang's kill-on-sight list.
Hugh then (quickly) moved to Chiba City where he was able to find someone to replace his lost eyes. Fortunately he had gotten really lucky (he calls it "good") at a casino back in CA, and therefore had some spare cash. All of it was used on the operation. The first thing he tried his hand at in Japan was pimping. He had some natural talent at figuring out which girls would do well in the oldest profession, but somehow he would rather have been the one on the purchasing end of the deal. Plus he found it strangely disturbing that he got more money from the people who "just wanted to watch". He got tired of this really quickly, and barely made enough to get by even when things went well. Hugh then decided that drug dealing was the way to go. After awhile he decided to try some drugs, but didn't really like what the lows did to him. Plus, he found that he was using up his profits by snorting his stock. Fortunately, he was bright enough (high enough willpower?) to put an end to his own drug use, but it was better for him to be a long ways away from the stuff, so he gave it up. When he told one of his long time customers he was out of the business, they got into a scuffle. She ended up biting his ear off right before he tranq'd her. He spent most of the money that the drug trafficking brought in by getting an implanted ear from his old doc.
Next he hit it big. With his newfound ear he found a new ability, being a critic (the second oldest profession). He found a really talented girl that others had ignored (also American). Not only were they perfect on a personal level, but also from a professional standpoint. He was her agent, and found nightclubs at which she could perform, and she delivered time and time again. Of course eventually they started living together and he got her pregnant. This ended up drying up their source of income. Shortly after this happened, his old gang started making inroads to his new 'hood. He left all his money with the girl and fled across the ocean to New Tokyo.
Early on in New Tokyo he used his talents to make a friend. While wandering around just having gotten off the boat he saw an attempted assassination. One gang group ambushed another (which appeared to have a fairly high level member in it) and left the ambushed group for dead before the cops could get there. Hugh taped the entire thing, found out which gang was ambushed and made contact. He freely passed on the information he had to the victim's gang leader, and so now the leader "owes him one". This brings us to the present, and the Dodgers still aren't calling...