Connaughton didn’t notice the bubble and, after selling the Mexican condo in 2007 for three times what he paid for it, he decided to buy pair of properties in Costa Rica, thinking he would flip one and build a villa on the other one. One of his clients at Quinn Gillespie was Genworth Financial, a mortgage insurer, and people who worked there warned him not to buy real estate until at least 2009. There were other warnings too. In 2007, Biden was running for president again, and Connaughton joined the campaign in Des Moines where a city councilman told him foreclosures were a top three issue among voters. He advised Biden staffers to make housing an issue, but Biden ignored him. Connaughton ignored the warnings, too, and closed on the Costa Rican properties for nearly a million dollars at the peak of the bubble.

Connaughton had raised more money for Biden than anyone else in Washington and became treasurer of the Biden campaign’s political action committee. Biden still hated the money game and still believed that debate performances would raise more money than donor phone calls. He was a consistently good debater but lagged in the polls. Connaughton spent all of December in Iowa.