Time recently called Sen. Rand Paul “The Most Interesting Man in Politics” in a cover story, but the publication might have more accurately called him “The Most Conflicted Man in Politics.”

In his quest for the 2016 GOP presidential nomination, the freshman Tea Party conservative from Kentucky has been reaching out to minorities and young people to try to remake his image. Some political analysts and policy makers warn, however, that Paul may encounter stiff headwinds on the campaign trail for straddling or flip-flopping on sensitive issues – issues that include the war against ISIS, immigration reform and privacy issues.

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“Trying to have it both ways is fairly common in politics, but there’s a cost,” said Larry J. Sabato, a prominent University of Virginia political scientist. “His likely presidential opponents in the GOP are already taking note. The opposition research reports on Rand Paul will be substantial. The TV ads write themselves: ‘Which Rand Paul are you voting for?’”

WHY THIS MATTERS

Rand Paul, a new Republican maverick with an eye on the future, doesn’t hesitate to break the rules of his club. He wants the GOP to be the party for Latinos and blacks, and to champion the middle class. That accounts for some of his split personality in terms of immigration reform. But he also brings a strong following among young people—a group coveted by politicos—and necessary for a win in 2016.

Sabato added, “Flip-flopping is a standard topic for negative political spots.”

Paul and his admirers insist he’s not flip-flopping so much as taking nuanced or highly principled stands.

Once labeled an isolationist on military and foreign policy matters, Paul reluctantly bought into the Obama administration’s airstrikes against ISIS jihadists in Iraq and Syria and even argued more recently that Congress should formally declare war.

He also warned that President Obama and many of his own Republican colleagues, including Sen. John McCain of Arizona, are on “a fool’s mission” if they believe they can arm and train “moderate” Free Syrian Army rebels to help combat ISIS, as part of the overall strategy.

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The former ophthalmologist, who radiates unbridled presidential ambitions and self-confidence, has urged GOP leaders to reach out more to Hispanics and blacks to broaden the party’s predominantly white political base.

In an April speech, he strongly argued against the deportation of undocumented immigrants. But after Obama’s executive order last week temporarily granting nearly five million illegal immigrants protection from deportation, Paul declared he “will not sit idly by” and let Obama bypass Congress and the Constitution.

Then there was his startling vote last week that helped torpedoed a Senate Democratic drive to rein in the National Security Agency’s surveillance of bulk telephone data – a practice Paul once denounced as “an all-out assault on the Constitution.”

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That legislation, the USA Freedom Act, sponsored by Senate Judiciary Committee Chairman Patrick Leahy (D-VT), offered what many viewed as the best chance for Congress to respond to public outrage over the gross government intrusion on their lives first divulged by renegade U.S. intelligence consultant Edward Snowden.

Paul said that after the vote he believed he had struck a blow for liberty because the bill would have extended several provisions of the Patriot Act, the post-9/11 measure that enhances the government’s spying authority. Paul argued that by killing Leahy’s bill, he could likely get a better deal next year when the deadline for renewing the majority of the Patriot Act provisions would loom.

The legislation’s supporters said Paul did a major disservice to the cause. Once Republicans control the Senate in January, many will be unwilling to approve anything that reduces the NSA’s powers.

“I don’t know anyone who thinks -- given the changes in leadership in the next session -- that anything better from a civil liberties perspective than USA Freedom has any chance of making it to the floor,” said Julian Sanchez, an intelligence policy expert at the libertarian Cato Institute. “Literally no one I can think of believes that more substantial reforms than USA Freedom is now somehow more likely.”

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This is not the first time Paul has left observers unclear about where he stands.

He sparked a furor during his 2010 Senate campaign by questioning the section of the 1964 Civil Rights Act that prohibits private businesses from discriminating based on race. He’s since evolved into a born-again advocate for minorities’ rights.

He joined with Sen. Cory Booker (D-NJ) in railing against the injustice of federal drug sentencing laws, favors restoring voting rights for some non-violent convicts, highlights inequality in education, and champions inner-city economic revival.

As for views on the Middle East, Paul has gone from condemning foreign aid to Israel as “welfare to a wealthy nation” – a no-no as far as most conservatives are concerned – to support for that country. Now he’s calling for cutting off all aid to the Palestinian National Authority.

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Once the campaign heats up, experts say Paul may have to spend time at candidates’ forums explaining and reconciling these and other conflicting positions.

“Sen. Paul will have to be ready to answer charges from his opponents that he is playing it too cute on the issues,” said Ron Bonjean, a political strategist and former congressional GOP spokesperson. “There are a number of issues Rand Paul will have to answer for, on stage in front of Republican primary voters.”

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