Outside Florida, Jeb Bush may be viewed as being more liberal — more reasonable and smarter — than his infamously witless, reflexively conservative brother, George W. But Floridians know better. As governor, Jeb was a right-wing hardliner — a doctrinaire supply-sider who slashed at least $14 billion in revenue to the state government by cutting taxes, mostly on the wealthy, and killing programs for the middle class and services for the poor. It was Jeb who signed Florida’s infamous “Stand Your Ground Law” and Jeb who tortured a stroke victim, Terri Schiavo, by ordering her to be kept alive artificially years after she’d suffered irreversible loss of brain function.

One area where Jeb’s positions are famously out of synch with the extreme right, however, is immigration. Last year he outraged tea party types when he expressed compassion for those who cross the border illegally. The undocumented, Jeb said, come to the United States seeking employment as an “act of love … an act of commitment to your family.”

Now a report in the Washington Post may explain why Jeb’s position on immigration is an outlier from conservative orthodoxy. It’s personal. His wife Columba’s late father, Jose Maria Garnica Rodriguez, was a undocumented worker from Mexico:

After World War II, it was common to cross the border without proper papers, said Columba’s uncle, Antonio Garnica Rodriguez, who made the trek, too. “We just went across the border, worked, stayed there for a while and came back.”

He said his brother later joined the “bracero” program, which allowed manual laborers temporary legal entry to the United States. Jose Maria got his “resident alien” card on Feb. 4, 1960. It indicates that his point of entry was El Paso, Texas. He moved back to Mexico in the 1980s.

By hard-line Republican standards today, the bracero program was essentially a form of amnesty, and — despite the fact that their sainted Ronald Reagan issued amnesty to 3 million “illegals” in 1986 — the GOP base despises the policy today. They also likely won’t like the fact that when Columba Bush’s father retired in Mexico he received Social Security checks from the United States for the rest of his life. He had every right to the money, of course, because he earned it legally.

Columba’s father’s undocumented status explains at least in part her reticence about Jeb’s presidential ambitions. Another part of it may be a dispute in Columba’s family over her claim that she permanently estranged herself from her father in the early 1970s after he beat her. Her father’s relatives have denied this — a denial that prompted the sort of imperious response for which the Bush family is known:

“We don’t intend to relitigate the numerous offensive actions of a deceased man who abandoned his family in poverty while Mrs. Bush was a young child,” Bush spokeswoman Kristy Campbell said in an e-mail. “Mrs. Bush, her sister Lucila, and her mother have remained close and severed ties with him more than four decades ago.”

Jeb’s outlier position on immigration may be out of synch with the base, but it lines up neatly with a sociopathic element of conservatism — a key personality trait that separates liberals from conservatives. Liberals do not have to walk a mile in other people’s shoes in order to imagine their plights, while conservatives can only grasp the consequences of injustice when they experience it personally.

It’s a dead cinch, for example, that Dick and Liz Cheney would be as virulently anti-gay as any of their co-ideologues if their daughter weren’t a lesbian. Similarly, after Ohio Republican Sen. Rob Portman’s son came out, he flipped overnight from opposing civil rights for gays to supporting them. Right-wing talk show host Joe Scarborough opposed gun control until the Sandy Hook massacre brought the horror of gun violence to his doorstep — he lives in Connecticut and had children the same age as those who were massacred at the elementary school.

In the 2012 cycle, Mitt Romney executed a record number of flip-flops — less politely known as “telling lies” — in order to distance himself from his liberal record. The GOP base is especially suspicious of its wealthy betters in the party, who benefit from the cheap labor undocumented immigrants provide. For example, Romney didn’t help himself when he explained why he fired a landscaping company at one of his estates. “We went to the company and we said, look, you can’t have any illegals working on our property,” Romney said. “I’m running for office, for Pete’s sake, I can’t have illegals.”

Given Jeb’s close family association here, flipping on this issue will represent a betrayal to the memory of his wife’s father and his children’s grandfather. On the other hand, if he decides to hold to his liberal position on immigration, he’ll face a firestorm on his right in early battleground states like Iowa, South Carolina and perhaps even Florida.