President Trump’s new national security adviser had a big booster before he entered government: his longtime friend conservative talk radio host Hugh Hewitt.

Robert O’Brien – now the outgoing Special Presidential Envoy for Hostage Affairs and a longtime corporate lawyer – worked with Hewitt at the Arent Fox law firm and, later, at O’Brien’s own O’Brien Larson firm.

The pair’s friendship extends back years. O’Brien also appears to have benefitted from Hewitt’s praise for their shared, hawkish foreign policy views, while appearing on the conservative talking head’s show dozens of times over the years.

Hewitt did not return an emailed request for comment.

Helping a friend

It’s not clear how long the two have known each other, though one source who knew both told TPM that the relationship dated to at least the mid-2000s.

Hewitt has boosted O’Brien for foreign policy gigs in GOP campaigns. A 2015 National Review article about O’Brien’s appointment as foreign policy adviser to then-Wisconsin Governor Scott Walker (R)’s failed presidential bid described Hewitt as a “friend of O’Brien.”

“I cannot have favorites in the race, but the O’Brien primary was fascinating to watch because many, many candidates wanted him to join their team for the simple reason that he knows everybody in the national-security world,” Hewitt told National Review.

O’Brien has been a regular on Hewitt’s radio show, even after his appointment as Special Presidential Envoy for Hostage Affairs.

The platform allowed O’Brien to expound on foreign policy issues while working as a corporate lawyer in private practice – not normally a prerequisite for the position of national security adviser.

After his appointment as Trump envoy in May 2018, the praise continued. O’Brien flew to Sweden in July 2019, for example, to resolve the case of A$AP Rocky – a fixation of the President’s.

And, more recently, Hewitt boosted O’Brien – along with ambassador to Germany Richard Grenell – while he was in the running to become national security adviser.

Next NSA up? Ambassador @RichardGrenell or Ambassador @robertcobrien? Both have broad national security experience, work well with and for @realDonaldTrump and @SecPompeo, both can start tomorrow with their clearances. — Hugh Hewitt (@hughhewitt) September 10, 2019

Legal work

Hewitt and O’Brien worked together at law firm Arent Fox, where O’Brien was managing partner of the Los Angeles office.

A lawyer familiar with the situation told TPM that Hewitt had an office at Arent Fox under O’Brien’s tenure, but that he would never see the conservative talk radio host in the office apart from when he was getting coffee with O’Brien.

O’Brien left Arent Fox to found his own law firm – Larson O’Brien – in January 2016. The press release announcing the move only named O’Brien, founding partner Stephen Larson, and Hewitt.

By next year, Hewitt had embroiled himself in a minor scandal involving the Environmental Protection Agency. The conservative commentator came under criticism after emails released in a lawsuit showed him brokering a meeting between EPA chief Scott Pruitt and O’Brien Larson attorneys representing a California Superfund location in a bid to have the EPA expedite the site’s cleanup. Hewitt dismissed the revelation as a “nonstory” at the time.

The firm has since scrubbed Hewitt’s name from its website. The only remnant of his presence at O’Brien Larson is the press release announcing the firm’s creation.

The Hugh Hewitt Speaker’s Bureau

TPM found that O’Brien was briefly slated as a speaker at Hugh Hewitt’s short-lived venture in running a paid public speakers’ bureau.

An archived version of the website for Hewitt Speakers shows that users were offered the chance to “Book Hugh Hewitt,” and also describes O’Brien as “an attorney and commentator on foreign affairs and international law issues.”

It’s not clear what became of Hewitt Speakers, though it seems that the venture’s last social media posts date to 2013.

Hewitt did not reply to a question asking him to elaborate on O’Brien’s fee, and what percentage of that would have gone to his bureau.

Hawking together

Much of the pair’s relationship appears to have focused on enabling – and spreading – their shared, hawkish views, all while burnishing O’Brien as a foreign policy hand.

Take the foreword that Hewitt wrote for O’Brien’s September 2016 collection of essays, titled “While America Slept: Restoring American Leadership to a World in Crisis.”

He writes, “don’t be surprised if O’Brien emerges as the key voice and guiding hand of a new and serious National Security Council in the West Wing, or at the Departments of Defense or State in 2017.”

Hewitt’s prediction may only have been off by two years, although he also writes of how O’Brien’s hawkish views were in demand by both the Walker and Mitt Romney 2016 exploratory teams.

The two wrote an article together in Politico in 2014 titled “Third Time’s the Charm,” demonstrating their political acumen by arguing that Romney stood a good chance at being elected president in 2016, if only he would run.

More recently – and more to the point of O’Brien’s nomination – the two discussed the appointment of O’Brien’s predecessor John Bolton as national security adviser on a March 2018 episode of Hewitt’s show.

O’Brien, a former Bolton aide, called the then-newly appointed national security adviser “the best lawyer foreign policy hand in America in either party on the other side.”

“He would know his brief, would know what his client, in this case, the president of the United States, wants,” O’Brien said, recalling the work Bolton performed as U.N. ambassador. “And it’s a very impressive skill set that he brings to the national security advisor position, and is going to serve the President well.”