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In any case, Cashill argues, Obama is immune to racism by virtue of his upbringing, which took place mostly in multiethnic Hawaii.
"The irony is, Clarence Thomas grew up about as black as you can grow up," Cashill says. "Raised by his grandfather who was a sharecropper, no indoor plumbing, all that stuff in the Jim Crow South. Obama, culturally, he's no blacker than you or I am."
Cashill, 63, grew up in Newark, New Jersey, in what he describes as a typical Irish-Catholic family. Poker games, horse races and the bottle were as much a part of their lives as Sunday Mass. His father, William Cashill, was a police detective who every day walked in suit and tie to the police station, at the end of their block.
Later, Cashill's father was made to work as a patrolman at a station across town. Blame for the demotion fell on ethnic rivalries within the police force. Forced to work nights in uniform, Cashill's father became sullen at home.
"He killed himself when I was 15," Cashill says. "It was the same year Kennedy died. They both died the same way, bullet to the head."
His father's experience hardened Cashill to political realities. "Yeah, I probably saw things a little differently than people who hadn't gotten that close to it," he says. "That was Newark. The guy who gave me my Eagle Scout badge died in prison."
Though he came from a cop family, Cashill decided not to pursue a career in law enforcement. "My mother would've killed me," he says.
Instead, he became a scholar. In 1982, he received a doctorate in American studies at Purdue University, where he met his wife, Joan FitzPatrick Dean. She accepted a job teaching English at the University of Missouri–Kansas City a year after they graduated.
Cashill, unsure about his direction in life, went to work for the Housing Authority of Kansas City, Missouri. He hated it. The bureaucracy was slow and, he decided, corrupt. "We [the staff] actually staged a walkout at one point because we didn't want to just take it," Cashill says. "You know how The Kansas City Star covered it? 'Three-Ring Circus at Housing Authority.' Just no attention paid at all."
It was around this time that he met R. Crosby Kemper III, the scion of the banking family and a lifelong conservative.
"He was still coming out of his liberal phase when I met him," Kemper says. "You know that quote, 'If you're in your 20s and you vote Republican, you don't have a heart. But if you're in you're 40s and you don't vote Republican, you don't have a brain?' It was that sort of thing, but Jack didn't need until his 40s to catch on."
Cashill and Kemper shared an interest in American literature. They talked about the scarcity of novels with businessmen as heroes and guessed that it had something to do with the prevalence of left-wing types in the arts.
Kemper says Cashill liked to argue, and he was good at it.
"One thing about Jack is that he's very calm," Kemper says. "I remember having a dinner at my house, and Jack was there, and there was also another friend of mine who's liberal. They got into a debate about abortion — Jack's pro-life. My friend who was a liberal just kept getting angrier and angrier as the debate went on, but Cashill just sat there totally cool and collected and just destroying the guy's arguments."