Despite being non-Evolved, prone to finding himself in dangerous neighbourhoods, owing money to dozens of bad people, being a recovering addict AND being really terrible with money, Gilbert Tucker has survived. It's sort of strange that people didn't start calling him 'The Roach' with all the close calls he managed to avoid. He ran a black market in E-Ville for awhile, shuttling goods to people in need under dangerous circumstances. It was a natural extension of his pawnie days. If anyone asked, he said he was just trying to make a living. He helped out enough people over the years that despite his illegal endeavors and claims of being a lowlife, he actually built up some goodwill and helped a good chunk of people. He made a few new enemies in the process as well, particularly with the authorities who suspected what he was doing.
Things got too hot for him at one point, and he was forced to flee New York. He's cagey about the exact reasons, but there's any number of possibilities ranging from calling in an old debt, to crossing the wrong person or getting too much attention from the authorities. It could be one of things things, it could be all of those things. It all adds up to the same thing, though: it was just too dangerous to stay in New York.
He ended up in Vegas, working for an old associate at an off-strip casino. He appraised goods that people wanted to chuck in the pot at poker games or change for chips. It wasn't exactly exciting or lucrative work, but it was relatively safe and allowed him to avoid politics.
Then, one day, Vegas saved his life.
On a whim, Tuck decided to play the slots at the Bellagio. Normally, he was more of a poker player rather than a slot zombie, but an associate was late for a meeting and he had a little time on his hands. It was one of those big, oversized slot machines with a huge top prize that had very little chance of ever paying out. Except, well, this time it did. With the pull of a one-armed bandit, Gilbert Tucker found himself five million dollars richer.
The elation was short-lived because the criminal network sniffed out his money and a lot of people called in old debts. By the time he'd paid off those he couldn't avoid. the fortune was whittled down to just over three milllion. A chunk of that money was quietly donated to old friends fighting back in New York City. Another chunk was held in trust for his son, should he ever surface to claim it. Despite his dwindling fortune, he found himself out of debt and not under anyone's thumb for the first time in his adult life.
After living the high life for a short while, Tuck once again felt the heat of inevitable conflict. He returned home to Toronto to see his sister after twenty years away. She had cancer and it was looking unlikely that she'd survive.
Although the circumstances of his return to his home city were tragic, it seemed once again that fate was on Tuck's side. Not only was he outside the country as it descended into civil war, he was far from the catastrophic explosions on the west coast. He suffered a personal tragedy in the death of his sister, but things would have been a lot worse if he'd stayed in Las Vegas.
It was morbid curiosity combined with a kind of bent nostalgia that brought Tuck back to New York in 2015. In a time when many Americans were pouring across the border to Canada, he made the reverse trip.
It might seem like it was a crazy idea to go back to New York, but in many ways, the broken city was his home. To his surprise, some people still remembered him there, and more for his work as a black marketeer during the E-Ville days than as the crooked pawnie on Staten Island. Being in New York and not under anyone's debt was a strange experience, and he found an odd sort of freedom. He ended up helping to set up a market in the Safe Zone, and then somehow ending up the coordinator of said market. And then somehow, somehow ending up as a councilmember.
In this new world, Tuck is only somewhat legitimate. His past as a criminal and a fence serves him well. He's more than willing to bend the rules when needed, even when he helped write some of those rules in the first place. He's nearly a dozen years sober (despite ample opportunities to regress to drinking or using) and he's even switched from cigarettes to an e-cig. Weed is still his drug of choice, but that's a little hard to come by in this economy.