Alter — whose second history of the Barack Obama era, “The Center Holds,” comes out next week — is puzzled about why a former Constitutional law professor allowed such a sinister turn. “What is it about Obama that he so disdains us?” he muses. “Presidents always hate leaks. Ronald Reagan said ‘I’ve had it up to my keister with these leaks.’ But they usually don’t act on it. Even if Obama didn’t personally sign off, people always sense by osmosis what leaders are thinking and go in that direction. His people know that leaks offend his sense of discipline and that he likes to protect his right flank by being tough on national security. “Kennedy had been a reporter, but Obama is not friendly with the press. And he has contempt for people who don’t do their jobs, and, when you talk to the press out of school, you’re not doing your job.” Alter, a fellow Chicagoan who thinks Obama has generally been a good president, has closely studied the central paradox about the man. “He won a majority twice in elections for the first time in half-a-century without liking the business he’s chosen,” the writer says. “He’s missing the schmooze gene.” As Bill Clinton noted, it was strange that Obama was good at the big stuff, like foreign policy, and bad at the easy stuff, like connecting to people. By 2011, Obama’s insularity was hurting him with Democratic donors, elected officials and activists, Alter writes, adding: “Democratic senators who voted with Obama found that their support was taken for granted. Many would go two or even three years between conversations with the president, which embarrassed them (constituents were always asking about their interactions) and eventually weakened Obama’s support on the Hill.” It was not only powerful committee chairs and many Cabinet members who rarely spoke personally to the president, Alter notes. It was only in his second term that the Obamas invited the Clintons over for dinner in the White House residence. Obama is not a needy person, but he needs to think of himself as purer than this town. He wanted to be, Alter writes, “nontransactional, above the petty deals, ‘donor maintenance,’ and phony friendships of Washington. Here his self-awareness again failed him. In truth, he was all transactional in his work life.” As Alter observes, “His failure to use the trappings of the presidency more often left him with one less tool in his toolbox.” Obama did not understand why his stinginess with expressions of gratitude and phone calls could sting, or fathom the thrill of letters from the president. “He fundamentally doesn’t relate to their impact because he wouldn’t particularly care if he got one,” the Obama adviser Pete Rouse explained to Alter. At East Room events, Alter writes, Obama’s vibe was clearly: “I’ll flash a smile, then, please, someone get me the hell out of here. It wasn’t that he had to be back in the Oval Office for something urgent. He just didn’t want to hang out for an instant longer than he had to, even with long-lost Chicago friends.” The president sometimes “exuded an unspoken exasperation: I saved Detroit, the Dow is up, we avoided a depression — I have to explain this to all of you again?” That attitude caused him to tank in his first debate with Mitt Romney. David Plouffe told Alter that Obama was “better suited to politics in Scandinavia than here,” meaning, Alter writes, “that he was a logical and unemotional person in an illogical and emotional capital.” Ironic, given that it was Obama’s emotional speeches that precociously vaulted him into the Oval Office. When Obama was elected, he assumed he would be a good bridge-builder. “But he just had no experience dealing with Republicans in any significant way,” Alter told me. “He wasn’t in the leadership in Springfield or the Senate. He thought that just because he mussed up Tom Coburn’s hair that he knew how to deal with Republicans.” On “Fox News Sunday,” Bob Dole told Chris Wallace that Obama “lacks communication skills with his own party, let alone the Republican Party. And he’s on the road too much.” The president will have to learn the hard way: You can go over the head of Washington but it doesn’t get you anything in Washington. The man who prides himself on his self-awareness is now trying to use more tools in the toolbox. So the main question, Alter says, is “whether learned behavior and his determination to have a successful second term and do things differently can win out against his natural inclinations.” The historian believes that Obama does have the capacity to change. “He gets it now,” Alter says. “Is it too late? I doubt it. He wants to be remembered for more than being the first African-American president.”