The forthcoming issue of the New Yorker features an engrossing 12,000-word deep dive into Sen. Rand Paul’s bid to take his libertarian conservative message mainstream ahead of a potential 2016 run for the White House.

The profile, by the magazine’s Ryan Lizza, rehashes familiar territory – Ron Paul’s racist newsletters, the notorious “Aqua Buddha” incident, and Paul’s train wreck of an interview with Rachel Maddow on the Civil Rights Act of 1964. But Lizza also unearths fascinating tidbits about Paul’s past and what may lie in store for the senator.

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From political tensions between Paul and his father to his long track record of support for legalized discrimination, here are five key takeaways from the piece.

Paul vs. Paul?

While nobody ever thought Ron Paul stood a serious chance of winning the GOP nod in either 2008 or 2012, Rand Paul would be a real contender if he entered the field. That’s largely because while Ron Paul fancies himself an anti-politician – with a penchant for rhetoric that infuriated large segments of his own party – his son is less keen to alienate GOP factions he would need to win in a general election, including more hawkish members of the party.

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As Paul readies himself for a 2016 campaign, his advisers are eyeing the former Texas congressman warily. After Ron Paul defended Russian President Vladimir Putin during the Ukraine crisis, one aide to Rand Paul expressed frustration with Ron Paul’s insistence on making impolitic statements.

“It’s good to see that the old man is still out there speaking his mind,” the aide told Lizza.

Speaking with Lizza, Rand Paul himself held his father at arm’s length. Condemning media outlets for scrutinizing the Pauls’ ties to extreme right-wing and white supremacist figures, Rand Paul said that he “was never associated with any of these people. Ever. Only through being related to my dad, who had association with them.”

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Clashes with religious conservatives in college

Rand Paul might be an anti-choice, anti-marriage equality, pro-creationist pol who makes appearances at venues like the Family Research Council’s Values Voters Summit, but he was more antagonist than ally to religious conservatives while a student at Baylor University, Lizza reports.

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With close friend George Paul (no relation), Paul would engage in fierce debates with biblical literalists, creationists and hard-line opponents of abortion rights. George Paul told Lizza that he and Paul would occasionally show up at area churches on Sunday mornings “to observe how people practice their spirituality” and seek out sparring partners. Paul’s communications director denied that the senator ever ventured into churches looking for “people to argue with on religious matters.”

Discrimination is an “inalienable” right

Ever since Rachel Maddow challenged Paul on his criticism of the Civil Rights Act of 1964, he has attempted to win over skeptical African-Americans and has angrily denounced reporters who seek clarification on whether he thinks government has a role in stopping discrimination.

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While Maddow’s 2010 interrogation of Paul was based on an interview he’d given just days before, Lizza documents Paul’s extensive track record of opposition to anti-discrimination statutes. In a 1982 letter responding to a pro-affirmative action Op-Ed, Paul wrote that the Op-Ed reflected a “mentality” that “ignores one of the basic, inalienable rights of man—the right to discriminate.”

Twenty years later, Paul would condemn the Federal Housing Administration’s anti-discrimination policies as a hindrance on “private property and associations.” According to Paul, “[u]nofficial, private discrimination” should always be legal, “even when that means allowing hate-filled groups to exclude people based on the color of their skin.”

“Avoiding taxes”

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In 1996, Paul and his ophthalmology practice partner John Downing split after three years working together. Downing told Lizza that their differences largely centered on Paul’s interest in “avoiding taxes.”

“He was a little bit more interested in avoiding taxes than I was. And I was afraid he was pushing things a little bit,” Downing told Lizza.

Paul, Downing feared, ““was taking more deductions than was reasonable.”

Eighteen years later, Downing told Lizza he now thinks he “was paying Uncle Sam too much” after all.

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A thaw with McCain?

If he runs in 2016, Paul will encounter fierce resistance from neoconservatives hostile to his non-interventionist inclinations. John McCain confidant Mark Salter has even said that if Paul captures the 2016 nomination, “Republican voters seriously concerned with national security would have no responsible recourse other than to vote for Hillary Clinton.” McCain himself has indicated he may do as much, telling the New Republic last year that a Clinton-Paul matchup would present him with a “tough choice.”

But McCain appears to have changed his tune, now vowing to support Paul if he’s the GOP nominee.

“I’ve seen him grow and I’ve seen him mature and I’ve seen him become more centrist,” McCain told Lizza. “I know that if he were President or a nominee I could influence him, particularly some of his views and positions on national security.”

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And therein lies Paul’s conundrum. Ingratiating himself to once-skeptical or even hostile elements of his party inevitably means disappointing many of his core supporters. Meanwhile, as Lizza’s profile illustrates, Paul’s assiduous effort to court voters outside the small circle of die-hard libertarian conservatives may be smart politics, but his effort to go mainstream will almost certainly be undercut by the reams and volumes of material Paul has provided opposition researchers for the past 30 years.