A gregarious man, Brady was a mainstay of Broadway nightlife. He often dined with popular society. After further investments in the stock market, Brady accumulated wealth estimated at $12 million, though not always by ethical means. According to biographer Harry Paul Jeffers, "On election night (1896), Brady won about $180,000 (equivalent to approximately $ in dollars) by making crooked bets on the William McKinley–William Jennings Bryan presidential election." He also enriched himself to the tune of $1.25 million (equivalent to approximately $ in dollars) through a shady stock deal involving the Reading Railroad.