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Be a leader, Kemp had been telling himself, and in 1988 he gave it a try. He ran for the presidency on a counter-intuitive platform of supply-side economics and inner-city enterprise zones. But his managers complained that he was unmanageable. The Quarterback Mentality, political consultant Ed Rollins calls it in Bare Knuckles and Back Rooms. "Quarterbacks think they can always make the big play and resent being controlled by anyone." To help him keep his speeches shorter, Kemp's campaign staff gave him a timer (which he ignored). Kemp resolutely refused to do the things that candidates need to do, such as call contributors and practice for debates. His campaign sometimes seemed more like a graduate seminar in macroeconomics. Rollins chastised Kemp for being abstruse, and Kemp would briefly reform himself, "but then it was back to mumbo jumbo like the gold standard, Malthusian theory, baskets of commodities, T-bill rates, Hannah Arendt and Maimonides." Kemp dropped out after being shut out on Super Tuesday.
In 1989 George Bush tapped his former rival to be Secretary of Housing and Urban Development and his government's house bleeding heart. From the start Kemp had to reckon with the fallout from his predecessor Samuel Pierce's scandals and a President unconcerned about urban problems. Hoping to use hud to launch his own war on poverty, Kemp persuaded Bush to support a $4 billion housing program that encouraged public-housing tenants to buy their own apartments. But the Democratic Congress allocated only $361 million for the program. In the Bush White House, Kemp was regarded as the opposite of a good soldier for criticizing the Administration's indifference on poverty issues. Only after the Los Angeles riots of 1992 did Bush take a page from the Kemp playbook, talking about enterprise zones, tenant ownership and welfare reform. But it was too late for L.A. and for Jack Kemp.
Starting in August 1994, a few of Kemp's closest aides put together a plan for him to make a presidential run in 1996. It called for 241 fund-raising dinners to bring in $35 million in cash. At the time Kemp still owed money from his 1988 campaign. The quarterback who had never made big bucks in the pros was now raking in some real cash, earning as much as $2 million a year from his speaking engagements. Steve Forbes tried to persuade him to run, but Kemp just could not get himself up for the game. He enjoyed retreating to suburban Maryland, where he and his wife Joanne, his college sweetheart and a devout Christian, created a home that could have been a model for a 1950s sitcom.
Instead of taking Forbes' early advice to run himself, Kemp joined the primary battle just as it was ending. On the very day that Dole seemed to be a shoo-in for the nomination, Kemp endorsed Forbes by complaining that he could not let the pro-growth agenda be ignored. Pundits wrote Kemp's obituaries, but curiously, it may have been Kemp's quixotic backing of Forbes that led the way to his nomination. The endorsement clearly showed that he represented a wing of the party that Dole had not been able to reach. After the endorsement, Kemp seemed to feel he had gone too far and bombarded Dole's campaign office with telephone calls offering help and seeking redemption.