The guilty plea cost E. F. Hutton business and began hollowing out the firm, but Connaughton survived. He worked in the public-finance department, specializing in underwriting tax-exempt bonds issued by state and local governments. One day, he came up with a marketable idea: in Florida, many towns and counties had huge pension liabilities, so why not arbitrage them? Create a fifty-million-dollar pension bond, borrow at four per cent, then invest the tax-free money for a few years, at six or seven per cent. “It was a kind of scam on the U.S. taxpayer,” he said later. But his boss was pleased.
At twenty-seven, Connaughton was an assistant vice-president, making more than a hundred thousand dollars a year, but this was not what he wanted to do with his life. By the end of 1986, it seemed clear that Biden would run for President in 1988. Connaughton knew an E. F. Hutton lobbyist who had connections to the campaign, and he got a job as a junior staffer, at twenty-four thousand dollars a year. No longer able to afford the lease payments on his new Peugeot, he traded it for his parents’ 1976 Chevy Malibu. As Connaughton recalled, “I had done Wall Street, and I was going to do the White House next.”
Connaughton’s first assignment was to find twenty people in Georgia to write the campaign a two-hundred-and-fifty-dollar check. After amassing that level of support in twenty states, a candidate qualified for federal matching funds. It was one of the hardest things that Connaughton had ever done, but the fear of failing spurred him, and he begged everyone he knew in Georgia to write a check. He succeeded in getting twenty people, and he learned something about fund-raising: you didn’t have to convince anyone that Biden was going to win, or even that he was right on the issues—only that you needed this, as a favor.
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