A Tale of Two GOP Advisers, Split by 2016

In 2005, Pierre-Richard Prosper didn’t know what he wanted to do, except leave Washington.

He had moved there after leading the United Nations’ first prosecution for genocide, and President George W. Bush had appointed him as the U.S. ambassador-at-large for war crimes. After 9/11, he had stayed to help develop U.S. counterterrorism policy.

Now what?

Prosper got a call from his friend Robert O’Brien, whom he had met a decade earlier through the U.N. Both hailed from Los Angeles, had headed off to do international work, and then moved to Washington. Now O’Brien was back in LA, and he had an offer for Prosper: Why not come join his law firm?

Prosper accepted, but neither of the friends could stay away from politics. In 2008 and 2012, the law partners worked as senior advisers to former Massachusetts governor Mitt Romney in his bids for the Republican presidential nomination.

For the 2016 race, they are once again advising presidential candidates — but they’re backing two different ones. Prosper has teamed up with former Florida governor Jeb Bush, while O’Brien is a senior foreign policy adviser to Wisconsin Gov. Scott Walker.

“When we were supporting the same candidate, we’d talk about issues all the time,” Prosper said recently. “Now, we keep it separate. I know where he is; he knows where I am.”

“I’m sure there will come a time when we’ll have to square off, and that’ll be interesting,” he laughed. “For now we’re keeping our cards close to the vest, waiting for that day.”

That day is Thursday, when Bush and Walker face off at the first Republican presidential debate in Cleveland.

“In politics, there’s always some competition,” O’Brien said. “Pierre is very committed to Gov. Bush, and I’m sure thinks he’s going to win. We’re feeling pretty good about the Scott Walker campaign.”

Wanted: National Security Experience

Prosper and O’Brien’s national security experience is in high demand and short supply as the GOP field stretches to 17 candidates, most of whom have little of their own. Many have called up aides from the last several decades’ Republican nominees – George H.W. Bush, George W. Bush, John McCain, Romney — in order to staff up and bolster their credibility on defense. Jeb “I am my own man” Bush’s team is composed mostly of his brother and father’s neocon advisors.

After two terms of a Democratic president who has steadfastly stuck to his doctrine of smart power and cautious force, the Republican contenders are striving to reclaim the standard of “strong on defense.” Proper and O’Brien’s split reflects the deep divisions in their party over the right way to do it.

O’Brien argues that a string of security crises, from Russia’s invasion of Ukraine to the Islamic State’s rise, undermine the front-running Democratic nominee, former Secretary of State Hillary Clinton. “Rather than a strength for her candidacy,” he said, “she’s going to have a lot of trouble explaining to the American people how the world is a better place as a result of her and President Obama’s foreign policy.”

Prosper cautioned that current threats “are not necessarily more prominent; they’re more visible.” Still, he said, “The Republican Party has always been strong on national security and strong on defense, and people have looked to the party for the answers to these questions. For the past eight years [of Obama], we’ve had more questions than answers.”

‘What America Should Be’

The day after Thanksgiving in 2001, Prosper received a phone call from Vice Chairman of the Joint Chiefs Marine Gen. Peter Pace and Undersecretary of State for Political Affairs Marc Grossman. Prosper had been charged by President Bush with determining what would be done with captured members of al Qaeda. U.S. forces had just caught 300 people in Afghanistan. “‘They’re yours,’” Prosper said, recounting the call. “‘What are you going to do with them?’” Ultimately, they chose to detain the prisoners in a military prison at Naval Station Guantanamo Bay, Cuba.

Prosper said this decision flowed from spending part of his childhood in Haiti. He’s the first in his family to be born in the U.S., and didn’t learn English until he was 6 years old. “It all comes down to the protection of people around the world,” he said. “It’s easy to almost dismiss it, ‘Oh jeez, it’s a shame these horrible things happen in foreign places’ … it comes back, and it comes back not only in the sense of the responsibility of the U.S. and promoting some of these democratic principles and ideals, it also comes back as we saw with 9/11, with ISIS.”

His family’s experience also “gave me an ability to hear and see how others, non-Americans, viewed America,” he said. “You hear what people say America should be.”

In this way, he says, he relates to Jeb Bush, who cites a trip to Mexico at age 17, where he met his wife, as his most formative experience.

Prosper alluded to the national security spectrum of the 2016 field, from the non-interventionist leanings of Sen. Rand Paul, R-Ky., to the more mainstream hawkishness of Sen. Lindsey Graham, R-S.C.

“It’s not about intervention or not intervention; it’s about U.S. leadership,” he continued. “It doesn’t necessarily mean the U.S. needs to be the pointy end of the stick … Our next president needs to have a view of the world not only as it is, but as it should be, and then use that as the vehicle to lead.”

‘A New Generation’

Shortly after passing the bar, O’Brien joined the Army Reserve JAG Corps, and simultaneously launched his civilian law career. He left the Reserve as a major in 2005, but his service led him to work with the U.N. Security Council from 1996 to 1998, where he helped review billions of dollars in claims from Iraq’s invasion of Kuwait. Later, he served for four years on a committee for justice reform in Afghanistan, starting under Secretary of State Condoleezza Rice and finishing under Hillary Clinton.

Along the way, he worked on the 2004, 2008, and 2012 presidential campaigns. “I promised my wife after each of the last three that I wouldn’t do another one,” he laughs.

“When you believe in the U.S. and the importance of the candidate that you’re supporting being elected to lead the U.S., you work pretty hard on the campaigns to ensure they get elected,” he said, calling Romney’s last run “a tough loss.”

“He absolutely has been vindicated on just about everything,” O’Brien said, quoting Obama’s one-liners from 2012 – “The 1980s are now calling to ask for their foreign policy back” — as if they still sting.

O’Brien tried to convince Romney to run in 2016, in part by writing an op-ed (“Third Time’s the Charm”), but the twice-failed presidential candidate said no. “One of the things he pointed out was a new generation of leaders, people like Scott Walker, who had a real opportunity to defeat Hillary,” O’Brien said.

When Romney bowed out, nascent campaigns scrambled to scoop up his infrastructure. O’Brien was courted by several (though he downplayed the notion that there had been an “O’Brien primary”). “I think I’m a pretty strong advocate of a robust American military, of American leadership in the world, and I try and at least do it in a way that’s civil,” he said.

This year, he was searching for someone who could beat Hillary, and unlike his law partner Prosper, wasn’t convinced Jeb Bush could do the job. He quipped, “It would be nicer to win than to lose.”

Bush’s Bookshelf

Imagine you are looking at a candidate’s bookshelf, Prosper said. “Does the person read only one kind of book, or does the person look at a range of books?” he said. “Jeb was not afraid to read a range of books."

“To me the choice was as clear as day,” he said. “I didn’t even have to think about anyone else.”

Prosper first met Bush in 1999, when Jeb was still governor of Florida and George W. was gearing up for his first presidential campaign. Prosper was working for the Clinton administration at the time, but he when heard last fall that Jeb was considering a run, he reached out to lend his support.

Bush — well-funded, well-connected, scion of a political dynasty — was expected to leap to the front of the field, but early stumbles fueled doubts. He struggled for days to clarify whether he would’ve invaded Iraq knowing what we know now. But he’s stayed relatively steady since, and has recently worked to position himself as the mature alternative to current frontrunner Donald Trump.

Prosper says Bush’s “front-row view” to the presidency is an asset, not a liability. But he emphasizes Bush’s individual experiences, as an executive of “a very critical state” and as a businessman. He said Bush “looks at a problem from multiple angles to find the solution. Other candidates in the race don’t have that ability.”

“Particularly given the issues that we are facing today, usually the answer requires a multi-faceted approach,” Prosper said. “The answer may be military, it may be intelligence, it may be rule-of-law enforcement, it may be development.”

Ultimately, he said, advisors are only a resource: “My job is not to tell the candidate what to think.”

Nor can Bush lean too heavily on anyone. “I do believe he is his own man,” he said. “Just because your father was president, your brother was president, even if you wanted to, you can’t do what they did — we are in different times.”

“When you bring in everything,” he said, “you have a recipe that I think makes him very attractive as commander in chief.”

Reagan Redux?

O’Brien says he’s “been impressed by Gov. Walker from a distance” since the hero’s welcome Walker received at the 2012 Republican National Convention. After Romney decided not to run again, O’Brien spoke to Walker over the phone on a topic he’s passionate about: rebuilding the Navy. A Wisconsin shipyard builds some of the Navy’s littoral combat ships, but O’Brien hardly expected the governor to be an expert on naval affairs.

“I was incredibly impressed by his depth of knowledge,” O’Brien said. “For someone who has not been as steeped in foreign policy and national security issues, he knew what he was talking about.”

A month later, O’Brien met Walker in Madison, and began talking to him and his staff regularly, particularly Mike Gallagher, a former Senate Foreign Relations Committee staffer and Marine Corps captain. When former senator Jim Talent, another sought-after national security advisor, committed to Walker, that clinched it.

But Walker struggled early to translate his domestic experience to international affairs. At the Conservative Political Action Conference, he said he’d confront the Islamic State the same way he took on pro-union protesters in Wisconsin. Later, at one of England’s most prestigious foreign policy think-tanks, he struck a discordant note, “‘Let the best cheese win.’”

“Look, it’s a long campaign,” O’Brien said of the gaffes. “Every candidate is going to say things inartfully, or are going to get asked a gotcha question.”

Walker now has a group of advisors, from military officers to former national security officials, to draw on, O’Brien said. “The governor started getting educated on foreign policy,” he said, noting Walker is briefed every morning “just like the president.”

“I went with the governor because I thought he was the candidate that was closest to Ronald Reagan,” O’Brien said. “He really is a peace-through-strength Republican who is committed to rebuilding our military capability.”

Walker has two distinct advantages, he said: one, Americans like electing governors, and two, he’s outside the Beltway.

“Where Scott Walker is really gonna shine through on foreign policy and national security is this is a guy who’s been tested,” he said. “He’s demonstrated a steadfastness, a resolve. People are gonna ask themselves, ‘Can I trust him in the next crisis? Can I trust his instinct?’”

To O’Brien, the answer is clear: Walker is the winner he’s been waiting for. Since 1990, his name has appeared on the ballot 14 times. He’s only lost twice.

“Marco Rubio can give a very fluent speech on foreign affairs, and Lindsey Graham has a right to pride in his service,” he continued. “But you have to look at the man … [Walker] may not have been on congressional delegations overseas, but he’s got the right stuff to be commander in chief.”

It’s that “right stuff,” this intangible Americana, that O’Brien believes will attract a wide swath of voters to Walker’s brand. “He’s one of these guys that just exudes Midwestern, traditional American values,” he said.

On Day One

As polls put Bush and Walker neck and neck, tensions have already erupted between their campaigns over the Iran deal, which has quickly become a fundraising and stump speech go-to among Republican candidates.

Walker pledged to kill the deal (before it even existed), and said it was “very possible” military action against Iran may be required, both on the “very first day in office.”

Bush said he wouldn’t necessarily “tear up the agreement on the first day,” pledging instead to consult with allies and his cabinet. In a dig at Walker, he said, “If you’re running for president, you know, I think it’s important to be mature and thoughtful about this.”

O’Brien says Walker’s stance on Iran exemplifies leadership, and he’s “surprised” at the Bush campaign. “The commander in chief has to be ready,” he said. Still, he added, “There’s a lot the president can do on day one to end this deal, short of war.”

In the job O’Brien convinced Prosper to take, he personally negotiated with Tehran over an Iranian-American retired businessman imprisoned for more than two years under accusations of “supporting terrorism against Iran.” Prosper’s experience also echoes Bush’s more patient approach: It took 14 months, hundreds of emails and three trips to Iran to win his client’s release in 2010.

“At one point I actually walked away from the table,” Prosper said. “It was hard, but I had to do it.” After about a month and a half, he said, “They came back.”

One national security expert goes with his gut, and a young but politically instinctive Midwestern governor who he thinks has the "right stuff." Another goes with the heir to a political dynasty founded on force-first foreign policy, believing him to be the deeper thinker. It’s a reflection of the party’s own division over whether winning the White House will take brazen new leadership or hewing to the tried-and-true, and whether its future lies with staying the traditional GOP path on national security or evolving to reflect a brave new world.