He carefully invested his money in New York City taxi Medallions for 20 years.
The Medallions give the owner a special right to service specific locations in New York City, like the airports.
He was a millionaire by age 40.
Then, Uber showed up, and won some court cases.
His Medallions lost 90%-95% of their value.
After that, he became Trump's errand boy for rent money.
I feel sorrier for the people who lost their investment and didn’t turn to dishonorable activities for their rent money. Mr. Cohen was a lawyer, so it’s likely that he was making some sort of living aside from his investment.