In the third chapter of Vinson Cunningham’s debut novel, Great Expectations, David Hammond finds himself on Martha’s Vineyard, fundraising among friendly wallets vacationing on-island. He is an aide to an unnamed Barack Obama stand-in (“the Senator”) who is campaigning for the 2008 Democratic nomination for president. As Karen Cox, the bundler David is boarding with, counts out sixty thousand dollars in checks — “twice my salary,” he notes — she...