UPDATE: The following post was originally published earlier this month, one day after Hugh Hewitt interviewed Donald Trump and asked questions about geopolitical conflicts and key figures which stumped the GOP front-runner. It has been updated to include information critical to Wednesday's Republican presidential primary debate on CNN. Hewitt, host of the "Hugh Hewitt Show," a radio program, will serve as one of the CNN debate's co-moderators. 

The list of people Donald Trump has lambasted, ridiculed and publicly derided is notoriously long. And this month, The Donald added another name when he called the much-respected conservative radio host and constitutional law professor Hugh Hewitt a "third-rate announcer," after an interview with Hewitt exposed what would appear to be some significant gaps in Trump's foreign-policy knowledge bank.

[Donald Trump just tripped up, over foreign policy. Again and again.]

On Wednesday night, Hewitt and Trump will face one another again when Hewitt joins two CNN journalists, Jake Tapper and Dana Bash, at the moderator's table for the second GOP debate. He'll pose more questions, and some of them will likely be directed at Trump.

To understand why Hewitt's participation in the CNN debate and his round in Trump's dis ring are worth noting, you have to know a little about Hewitt. By most accounts, Hewitt brings something relatively rare to the talk radio space. In the 15 years that "The Hugh Hewitt Show" has been on the air, he has run an often-but-not-always-calm operation, closely monitored by politicos and reporters alike. It's a show where guests can expect tough but typically fair questions that ultimately reveal not just what they think, but how they think. And what they say to Hewitt, more and more, will likely also be reported elsewhere.

Hewitt, 59, is a married father of three and a grandparent. A Harvard-educated lifelong conservative, Nixon loyalist and one-time lawyer in the Reagan White House, Hewitt is straightforward about his political leanings and aims both on- and off-air. He wants to transform the world into what he believes will be a better place by electing conservative pragmatists (he was a serious and early Romney supporter in 2012) and implementing conservative policies.

He's an unabashed member of the ideologically driven journalist corps. But Hewitt also has a reputation for facilitating rich and respectful on-air conversations with guests whose own political loyalties lie far afield from his own. And yet, somehow, he also remains a go-to outlet in good standing with Republican Party officials, candidates and office-holders. In short, Hewitt haters like Trump can be hard to find (except perhaps on Friday morning among Trump supporters).

Here's why:

Hewitt, a professor at the Orange, Calif.-based Chapman University Fowler School of Law and a practicing lawyer specializing in matters related to endangered species, has a collection of personal friends and professional contacts that spans the political spectrum. The list is -- for many Republicans and Democrats alike -- enough to boggle the mind, the National Journal magazine reported in a profile earlier this year.

Hewitt's best friend is Harvard roommate Mark Gearan, who also happens to have been President Bill Clinton's communications director. His University of Michigan law school classmate, Anne Gust, a Democrat and wife of California Gov. Jerry Brown (D), is another. Not to worry, Hewitt graduated cum laude from Harvard and picked up academic honors in law school, too. So, he can certainly hold his own in conversation with liberal friends.

But his connections on the right are also deep-rooted. Just out of college, Hewitt helped a then-recently disgraced Nixon research a book, and he clerked for the likes of judges Robert Bork and Antonin Scalia. He also put in time with the non-conservative judge Ruth Bader Ginsburg. Scalia and Ginsburg, of course, now sit on the Supreme Court; Bork was unsuccessfully nominated. And during his tenure in the Reagan White House, Hewitt worked alongside the now-U.S. chief justice, John Roberts. Hewitt also served as deputy director and general counsel of the Reagan administration's Office of Personnel Management and general counsel for the National Endowment for the Humanities.

Hewitt describes himself as a national-security obsessive who shares the very Reagan belief that a big and well-equipped military will dissuade attacks but that the country should also stand constantly ready for actual war.

Hewitt's show's guest lineup has already included many of the men and one woman vying for the GOP nomination in 2016. But the famed leftist constitutional scholar, lawyer and law professor, Erwin Chemerinsky -- Hewitt's colleague at the nearby University of California at Irvine law school -- is also a show regular, as was the late Christopher Hitchens before his death in 2011. This week alone, Hewitt has interviewed Republican presidential contender Lindsey O. Graham, the senator from South Carolina, and twice questioned fellow candidate Carly Fiorina.

The man's dinner parties and social-media timelines must surely be epic.

The range of ideas to which Hewitt is regularly exposed and his clear capacity for deep and original  thought also make him an interviewer for whom guests should always prepare. The thing about Hewitt's questions -- the thing that Trump's masterful publicity machine almost certainly was aware -- is that little that's said on Hewitt's show stays there. Hewitt might not run a show for those who like their entertainment with a side of politics. He certainly has a audience considerably smaller than conservative radio giants like Rush Limbaugh. But Hewitt and his staff have perfected the art of making what they do news and being a go-to for serious political watchers.

Hewitt's Southern California-based show not only attracts top-tier guests, but it makes accurate transcripts -- documents that include not just the questions asked and every bit of the answer, but the context in which those questions were posed and an easily accessible headline -- available online not long after the show. They dispatch those same transcripts to political reporters all over the country in short order. And when there's something that's newsworthy, it gets written about.

The list of ready excuses when an interview does not go according to a campaign's plan can grow awfully short and thin when people can read not just all the details of one interview (click here for the Trump interview transcript) but most of Hewitt's interviews for themselves, online. It also probably does not hurt that Hewitt has a son working in the Republican National Committee's press office, has written several books and writes weekly columns for the Washington Examiner and Townhall.com.

In 2006, when the New Yorker wanted to profile Hewitt, Hewitt struck a deal with the reporter assigned the piece, Nicholas Lemann. He would participate in Lemann's profile if Lemann, then dean of the Columbia University Graduate School of Journalism, would let Hewitt follow and write about him for the Weekly Standard. What emerged was a pretty nuanced take on the state of journalism and its institutions, including the revered J-school. Of course, Hewitt, a member of the right-wing with pride media, couldn't resist a little dancing on what he saw as the stately grave of mainstream media. In his 2005 piece in the New Yorker, perhaps the country's most celebrated magazine covering the whole range of politics, public affairs and culture, Lemann called Hewitt "the most famous conservative journalist whom liberals have never heard of."

If Hewitt's show, broadcast on 120 stations across the country every weekday, hasn't been enough to change that, a turn in the Trump ridicule chair and the CNN debate probably will.