One day it’s a banquet hall on the South Coast of Massachusetts. The next day it’s a temple in Concord, New Hampshire, home to a Freemason sect whose worshipers like to wear red fezzes and drive miniature cars. A couple of weeks later, it’s a tavern in Maine. After that, a nightclub in Malden. These are some of the places Howie Carr has been spending his weekends lately, renting them out for stage shows in which he relives his favorite moments from the 2016 election. “The Deplorables Show,” he calls it. You can learn a lot about Howie by going to one.
The show I attend takes place in September, at the banquet hall in Achushnet, a blue-collar hamlet of 10,000. When I get there at 11 a.m., Howie is sitting behind a table in slacks, brown loafers, and a button-up shirt, signing books. He looks good for 66. He’s also had hair transplants, liposuction, and gastric sleeve surgery, which listeners of his WRKO talk show may know, since he promotes weight-loss and hair-restoration procedures on the air. Today’s production technically runs from noon to 2, but dozens of “VIP” ticket-holders have arrived an hour early for a meet-and-greet. Except for a couple of Hells Angels types in their leathers, the crowd is populated by exactly the white, middle-class empty-nesters you’d imagine listen to Boston’s longtime king of conservative talk. Howie’s wife, Kathy, who runs the business end of his small empire, monitors the action from behind a merch table, wearing a purple blazer and pearls.
The VIP experience turns out to be a minor scam. The meet-and-greet consists of you shaking Howie’s hand, getting one of his books—plus a pair of plastic “lock her up” handcuffs—then being shuffled off the receiving line. In fact, most of these VIPs are not VIPs by choice. When Howie announces a Deplorables Show, his website offers only VIP tickets, one of which I bought for $75. Later, he releases “Cheap Bastard” tickets—for this performance, $35—which entitle fans to the exact same show, minus the receiving line.
Speaking personally, I am not made to feel like a VIP. On the radio and in his Boston Herald column, Howie is sarcastic, crude, and proudly chauvinistic. A gunslinger in a target-rich environment, picking off liberal moonbats and PC weenies. In person, he is surprisingly withdrawn, and proves unskilled at making small talk with his fans. Likewise, before I started reporting this story, I assumed Howie was a cocktail-circuit fixture. Turns out no. He tends to stick to his house in Wellesley, venturing out mainly for events like these. When the VIP line thins out, I introduce myself. Howie avoids eye contact and utters a few monosyllabic noises. “How you doing? Hi. What? Oh, okay. Oh, okay. Great. Okay. Good. Okay. Great.” I move on and find a chair.
Today’s Deplorables Show also features Ann Coulter, the veteran pundit with the Legolas-blond hair. In the spirit of not getting what you paid for, Coulter is caught in traffic and arrives an hour late for the event. When she does show up, the audience settles in and somebody from a local radio station warms up the room. “Are you ready to smoke Pocahontas?” he asks. Also here today is Geoff Diehl, the sacrificial-lamb Republican vying for Elizabeth Warren’s Senate seat. Howie has been hosting fundraisers for Diehl all year. In theory, being a thrice-weekly newspaper columnist precludes you from openly flacking for a politician, but the Herald apparently does not mind. Diehl leans in for a selfie with Howie and Coulter, who are waiting in the wings, near the bar by the side of the stage. Good time to mention that the bar is empty, and no food or drinks will be served.
The main event begins. “Thank you so much for coming out,” says Howie, looking more comfortable now. “Is everyone here a Deplorable?” The show works like this: We sit and watch videos from Donald Trump’s presidential campaign, while Howie and Coulter supply running commentary. Imagine a MAGA version of Mystery Science Theater 3000. After some WiFi issues are resolved, Howie’s radio producer and second banana, Steve Robinson, begins cuing up the video clips.
First up: Trump’s down-the-escalator campaign announcement. “The Mexican rapist speech. Oh. My. God,” Coulter coos. “I mean, I loved the Mexican rapist speech.” The hits keep coming. Howie enjoys footage of Trump berating a Hispanic television reporter. Coulter mocks a “fat illegal” who had asked to hug her during a town hall event. When Robinson for some reason cues up the Access Hollywood tape, Howie reminds the crowd, “Now remember, he’s just goofing around with Billy Bush.”
For the grand finale, we are forced to watch a gratuitously long clip of Hillary Clinton having a coughing fit. Here the audience locates its decency and goes a little quiet. Howie doesn’t seem to notice. “Lock her up! Lock her up! In a sanitarium—for tuberculosis,” he brays. Next, a clip of Clinton falling down in lower Manhattan. His analysis: “Timber!”
I’m not surprised by the tastelessness of the material. Low-rent juvenilia and ad hominem viciousness have always been part of Howie’s act, even if he is usually more clever about it. I am, however, struck by how lamely partisan it is. At one point during the show, Coulter tells Howie she’d welcome a Republican primary challenge to Trump from someone who might actually “build the wall.” Howie responds by clamming up and changing the subject. Coulter, for all her curdled nativism, has a handful of convictions that supersede her loyalty to the president. Howie, evidently, does not.
Welcome to the Howie Carr experience, circa 2018. His latest book, What Really Happened: How Donald J. Trump Saved America from Hillary Clinton, is a work of shameless hagiography. His radio show, which broadcasts nationally on the website and TV channel Newsmax, itself run by one of Trump’s closest friends, does stout work defending the president against his enemies. As Howie’s fealty to the White House has increased, the originality of his written work has stagnated. In a recent Herald column, he managed to refer to Elizabeth Warren six different times as “the fake Indian.” Online, you can find him retweeting random Breitbart crap about immigrants or Cardi B.
For all of his efforts, Howie has been rewarded with entrée to the president’s orbit. In 2016, he hosted rallies with Trump and lunched with him on his private jet. In 2017, Kathy and Howie joined Mar-a-Lago. To help defray the membership fees, he churns out hastily written, self-published books, sells right-wing tchotchkes on his website, and stages events like this one. As if to resolve any lingering questions about his journalistic independence, Howie will take his Deplorables Show tomorrow to New Hampshire, where he’ll be joined by special guest Corey Lewandowski, Trump’s former campaign manager.
You may think Howie Carr has been a bigot forever and are therefore not surprised by his lateral move into Trump bum-kissery. But it wasn’t always this way. Unlike other Trump sycophants, including Rush Limbaugh and Sean Hannity, Howie had tremendous journalistic talent. He made his reputation not as a drive-time shock jock but as a populist muckraker, gleefully exposing the corruption, nepotism, and depravity that pervaded Beacon Hill.
And that’s what really gets people about Howie’s new incarnation. It isn’t his hard-right line or his penny-ante side hustles. It’s that he seems to have sold out his old self in the service of all that. “Donald Trump is everything that Howie says everybody else in politics is,” says a former longtime Herald colleague. “A liar, a grifter, a womanizer. You know, take your pick.” For those old enough to remember his heyday, Howie’s love affair with the president is demoralizing to them. After all, says Peter Gelzinis, a former Herald columnist who for years sat across from Howie in the newsroom, “There’s a kind of exquisite irony that the guy who was seen as the great white hack-hunter has suddenly become just an unabashed shill for Trump.”
So what really happened? There are clues in his upbringing. Howie Carr was born in Portland, Maine, to a mother and father who spent their lives serving rich people. His childhood was split partly between Palm Beach, Florida, where his father worked at the Breakers resort, and Greensboro, North Carolina, where his mother was secretary to a local CEO. When she later took a job as the assistant to the headmaster of Deerfield Academy, her husband followed her there and became manager of the school store. Howie attended on scholarship. His senior year, he was accepted to Brown University, but says he couldn’t afford the tuition.
Surrounded by elites, but not admitted to their ranks: good preparation for the rest of his life. After graduating Phi Beta Kappa from the University of North Carolina, then a stint at a small newspaper, Howie took a job in 1979 at the Herald, where he fit right in playing lunch-pail foil to the Boston Globe. When most were too chicken, he hurled Molotovs at Whitey and Billy Bulger, the mobster and politician brothers whose good fortunes rose in parallel. He so mercilessly tormented “Fat Boy” Ted Kennedy, whose sexual misconduct and general debauchery tended to go uncovered elsewhere, that the senator unsuccessfully tried to use his legislative power to force the Herald’s conservative owner, Rupert Murdoch, to sell the paper.
Howie’s favorite targets were people who were full of shit: hypocrite save-the-whales types who were shabby to the help; chair-spinning “public servants” who leeched off patronage jobs. (One classic Boston magazine piece he wrote in 1985 began with this joke: Q: Why don’t state workers look out the window in the morning? A: Because they want to have something to do in the afternoon.) Mostly, he said what you weren’t supposed to say out loud. Infamously, he insisted on IDing a weight-challenged House speaker as “George Keverian (D-Papa Gino’s).” Billy Bulger, he called “the corrupt midget.” Etc. Publicly, you clutched your pearls. Privately, he was your guilty pleasure.
You know what he wasn’t? A conservative ideologue. If Howie tended to ream Democrats, that’s because Massachusetts was full of them. “What he perceives,” the veteran Democratic consultant Michael Goldman told the Boston Phoenix in 1987, “is the pomposity of power.” He was, in his impish way, looking to spill people’s milk. Howie ended up inspiring a generation of tough-guy journos—such as WEEI’s Gerry Callahan—who aped his cynical style. “As a young reporter starting out, I looked at his work with a fair amount of awe,” WBZ political analyst Jon Keller tells me. “If you took the overall body of work he has done over the years, documenting and exposing patronage, and the I’ll-scratch-your-back-you-scratch-mine behavior on the taxpayer dime, if you put it in a Globe ‘Spotlight’ layout, it’d be a sure Pulitzer Prize winner.”
But that might have hurt his proto-Deplorable brand. “The Globe is part of the establishment,” he told the Washington Post in 1989. “They’re saying the unwashed masses, as exemplified by me, have gone too far. That’s been a rich reward, to see the Globe become so irritated with me.” In the 1990s, he landed his own radio show, elevating him to a new tier of wealth and fame. Yet he clung to his blue-collar persona—and cheapskate tendencies. Gelzinis says that Howie, among other staffers, used to pad his expense reports, and drove around in demo cars that dealerships loaned him. At WRKO, an ex-colleague remembers him absconding with toilet paper and paper towels: “His arms were full, like he was making a trip to BJ’s.” According to Steve Robinson, his producer, Howie still hoards empty bottles and cans to collect on the 5-cent deposit. I saved the best for last: After he and his first wife split up in the early ’90s, Howie lived in—of all places—a rent-controlled apartment in Cambridge.
(Howie didn’t respond to my queries about the goosed expense accounts and paper-towel heists. Kathy told me, “I’m not going to respond to the Peter Gelzinis stuff. You can write whatever you want.”)
Meanwhile, Howie’s new devotion to the drive-time radio format was turning him into a caricature. In 1995, before Timothy McVeigh’s arrest, he repeatedly pinned the Oklahoma City bombing on “towelheads.” Howie’s populism took on a predictable shape: He skewered not only liberal elites, but also the minorities they supposedly coddled in their craven thirst for votes. Illegal aliens. Welfare queens. Gay people in general. In 2004, after Massachusetts legalized same-sex marriage, Howie lost his shit in embarrassing fashion. “If it happens in Abu Ghraib prison, it’s a war crime. If it happens at a rest stop on I-495, it’s true love,” he wrote in a column, going on to blame “black-robed tyrants” for their “sanctification of sodomy.” Polygamy, incest, and bestiality were invoked.
On the one hand…what the hell, Howie? On the other hand, these sorts of weird spasms launched him into Archie Bunker territory, where he could be laughed off by polite society. And yet, he had his moments. In 2006, his book The Brothers Bulger cemented him as a go-to Whitey whisperer and landed on the New York Times bestseller list. As time wore on, he became a kind of survivor. Globe columnists Mike Barnicle and, later, Kevin Cullen were tarnished by fabulism scandals. Herald guys like Gelzinis retired or got axed amid the paper’s many bloodlettings. Yet Howie remained, name-checking the buried bodies, raging against the dying of the light, and so on. So what if it was shtick? You knew you’d miss it one day.
Then came Trump.
Howie first wrote about Trump’s presidential campaign in the summer of 2015, not long after he announced his candidacy. “Pesky Facts Confirm Donald Trump Right on Illegals” ran the headline. The column could have been written by an algorithm. “Even the moonbat media can’t ignore the tsunami of violent crime being committed by welfare-collecting illegal aliens,” Howie wrote, jamming all of his favorite topics into one sentence. “Illegals are running amok, and the media are angry—at Donald Trump! Odd, though, isn’t it, how the Beautiful People still won’t acknowledge what open borders hath wrought?”
Howie’s next column was about Trump, too. “The other candidates are fighting the last war. They want to get a kiss from George Will, a pat on the head from Mitt Romney,” he wrote. “Trump couldn’t be bothered.”
Well, that was easy. Howie had found his man. “The issues Trump spoke to were the issues Howie and his audience cared about: fighting the entrenched political establishment, and illegal immigration,” Steve Robinson says. Besides, Trump made for fun radio. And if he was boosting ratings, Robinson says, “It’s not our job to go searching for reasons to criticize [him].”
There were other benefits, too. Later in the summer, car mogul Ernie Boch Jr. decided he wanted to throw a fundraiser for Trump at his mansion in Norwood. Ernie knew Howie a little and Howie knew Corey Lewandowski a little, and next thing you knew, everyone was best friends and Howie was riding on Trump’s plane, throwing the candidate softball questions at campaign events. Soon, his daughter Charlotte—he has five daughters from his two marriages—landed an internship at the Trump Organization, and after that, another internship, at the White House. According to her LinkedIn page, she’s now working full time for the Trump administration’s Overseas Private Investment Corporation, a federal agency. Factor in the Mar-a-Lago membership, and ta-da, Howie was a full-blown toady.
By the time Trump became president, Howie was touting his connection to the White House as the foremost achievement in his career. Last year, he staged an “Ask Me Anything” on the Reddit thread r/The_Donald. “I had President Trump on my show more than a dozen times throughout the campaign season, including election night,” he wrote, by way of introduction. “Here’s me with President Trump on his jet. And at Mar a Lago for NYE. Here’s me at an inaugural ball with Paul [sic] Jones and Juanita Broaddrick. Follow me on Twitter to get great pics like that!”
Howie’s radio mentor was a man named Jerry Williams, Boston’s original dean of AM populism. Williams used to drop a line on the air that went something like this: “I never had a dinner. When’s someone gonna throw me a dinner?” A pioneer in his field, Williams nonetheless felt disrespected by the Globe, the yuppies, the public radio crowd. And he may have been on to something. After he died in 2003, I heard from one mourner, hardly anyone showed up at his wake.
Howie has some of that Rodney Dangerfield in him, too. “People in talk radio get the fact that they’re widely reviled. They claim to relish in it, but I think it also rankles,” says a veteran local journalist who’s known Howie for decades. When Trump emerged, the candidate’s injured vanity and outsider insecurities proved contagious. The journalist continues: “‘Obama looked down his nose at us’; ‘They called us Deplorables’; ‘The beautiful people’; ‘The lamestream media.’ In a way, Howie’s abdication to the cult of Trump is really just the solidification of his grievance.”
But now, Howie’s finally getting his dinner. And he wants to eat well.
A couple of months ago, I called Howie to ask him if he’d talk to me for this profile. He said no and abruptly hung up. This was disappointing. I was hoping to get to know him. I’ve always regarded him as a slightly tragic figure, akin to a comic book antihero who uses his powers for all the wrong reasons. Why, I’d love to ask him, does he deploy his wit and intelligence so abjectly? Robinson told me Howie wasn’t going to talk to me because, despite being one, he “doesn’t respect reporters.” I think it’s possible he’s just shy. The last time this magazine sent someone to talk to Howie, for a 2007 piece about Republicans in Massachusetts, he spent the entire interview with his back to the writer.
The good news is, even if Howie Carr declines your interview request, you can just buy access to him. Every Tuesday, the Howie Carr Show offers lucky listeners a “VIP” experience in which they can pay to watch the show from the control room, behind a glass window. VIPs are also entitled to the familiar garage sale of books, Trump-y swag—“Make Christmas Great Again” sweatshirt, anyone?—and Chinese food, provided gratis by longtime friend-of-the-show Kowloon. Lucky for me, a “Cheap Bastard” deal is on the week I decide to attend, entitling me to a $100 ticket, marked down from the original $125. “There are two goals of the Howie Carr Radio Network,” Kathy Carr tells me, joking but not joking. “Number one, to make money. Number two, to make money.”
In that vein, the election of Donald Trump isn’t just a partisan win for Howie Carr, but a branding opportunity for Howie Inc. A few years ago, he broke away from WRKO and set up his own shop, syndicating his show to stations around New England. Absent a traditional patron, he’d hitch his wagon to Trump’s extended media apparatus. Business-wise, the basic idea was that he could make a lot more dough owning his own product than being a salaried employee of a radio station. Same goes for the paperbacks he sells at Deplorables Shows and remote tapings. What he sacrifices in quality, he makes up for in low overhead.
As it happens, Howie’s conflict-ridden support for Senate candidate Geoff Diehl also turns out to be a business opportunity. Why, one might wonder, has Howie invested so much time in a doomed candidacy? Maybe because Diehl has invested in Howie, too. According to the Federal Elections Commission, the Diehl campaign has bought more than $125,000 worth of advertising on the Howie Carr Radio Network since May 2017.
Kathy, a former salesperson at WRKO, is the architect and driving force behind the radio network. A petite, tightly wound woman, her aggressive sales tactics have hastened her husband’s transition from celebrated local journalist to human moneymaker. She is lauded in the industry for creating a syndicated radio network from scratch, though closer to home she is appraised less kindly. “She’s gonna work that guy till he dies, making sure that he’s making money,” says a local media figure who knows Howie well.
Several years ago, Casey Sherman, who cowrote the book Boston Strong, about the marathon bombings, put on a number of true-crime stage shows. He put Howie on the bill, and asked him to tell stories about Whitey Bulger. After a handful of performances, Howie called him and said he had to pull out. “He says, ‘My wife doesn’t want me to do it anymore,’” Sherman recalls. “He said, ‘Will you talk to her?’ And for the next 20 minutes, she goes off to me in a way that would make Mel Gibson blush. It was the most bizarre, outrageous phone call I’ve ever had in my life, accusing [Howie] of gathering groupies at the show, which was crazy, because the only people showing up were 64-year-old women and Howie’s crazy fans.” Not long after, an announcement landed in Sherman’s inbox for “An Evening of Crime with Howie Carr, Coming Soon to a Town Near You.” Howie Inc. had apparently ripped off his show. “Everybody that she meets or talks to, she tries to steamroll,” Sherman tells me. “She’s the power behind the throne.”
In response, Kathy tells me the partnership actually fell apart because Sherman wasn’t paying Howie what he had promised. Her own version of the show, she says, was more lucrative. “I don’t even want to tell you how much money we made,” she tells me, “but way more.” Reacting to the general perception that she’s turned her husband into a slave to Lord Mammon, Kathy shrugs, comparing herself to Yoko Ono. “When you’re in business and you’re the woman, and you tend to be a little successful, you tend to be seen as the bad person.”
Howie’s studio is located in Needham, on the third floor of a building in a blah office park off I-95. Given all I’d heard, Kathy proves a welcoming host when I arrive on a rain-drenched Tuesday for my VIP viewing. Like a wedding guest from hell, I am both completely unwanted and impossible to dislodge. Making my visit less awkward, I am joined by some fellow VIPs: a family of four from Georgia, visiting Boston via RV. Today, Howie is dressed in a pullover sweatshirt touting Mathews Brothers—his show’s main sponsor, a window company—that will be visible to viewers via the show’s Newsmax TV and Facebook Live simulcasts. Beyond that, I cannot convey many colorful details about him. Over the next four hours, he will shuffle in and out of his studio without once communicating with us.
Absent Howie’s cooperation, Kathy takes it upon herself to make sure I get my facts straight. “If it’s a good article,” she says, she’ll treat me to dinner at Mar-a-Lago. “If it’s not, I’ll buy you a coffee at Starbucks!” She later clarifies that she was joking and not trying to bribe me. After the show begins, she pokes her head into the control room to tell me something. She had heard that I had heard that Howie faked an address at a Chapel Hill YMCA to afford in-state tuition at UNC 45 years ago. This, she says, is not true. His parents kept a house in Greensboro the whole time. “His brother still lives in that very house,” she says. I ask what he does, and she tells me he works as an actuary. “Nobody had any learning disabilities,” she says with a chuckle. “Howie, you know, had an 800 on his History Achievement Test at Deerfield. He had the history award.”
At that moment, Howie passes by, and Kathy calls out to him: “Where is the acceptance letter to Brown?” “I got it,” he says. He beelines for his office and immediately starts rifling through his desk, like a squirrel searching for a long-lost nut. “This is why Howie doesn’t like affirmative action,” Kathy explains. “Somebody else got his scholarship.” He can’t find the letter. “Anyhow,” she continues, “he did get accepted to Brown.” (As if this moment weren’t uncomfortable enough, I actually did go to Brown.) “I think it’s at home in the yellow desk.”
Later, Kathy locates the letter and texts me a picture of it. She also calls to let me know that while some people think Howie is a nasty person, they are both actually quite the charitable givers. After that, Kathy keeps the exchange going via text message.
Most liberals are really conservatives.
That’s why so many Dems switched over for the presidential race.
And so-called libs often never give to the truly needy.
I knew Howie wore a chip on his shoulder. I didn’t realize Kathy carried it for him in absentia. Despite their considerable professional success and expanding personal wealth—to say nothing of their connections to the most powerful person in the world—the Carrs don’t seem willing to admit that they’re more in charge than ever. Maybe if they did, they’d see something they didn’t like.
The show I watch with the Georgians begins a little after 3 p.m. Howie sits alone in his booth. On the other side of the glass is Steve Robinson at the controls, and behind him the five of us VIPs in swivel chairs. Today’s episode kicks off with a replay broadcast of a surreal conversation between Howie and a scuba diver who claimed expertise about Ted Kennedy’s culpability in Mary Jo Kopechne’s death. It’s good radio. But it aired 24 years ago. The current version doesn’t quite hold up.
The news of the day is Brett Kavanaugh’s then-pending Supreme Court nomination, still in doubt over allegations of sexual misconduct. Howie seizes on a New York Times report that Kavanaugh had once thrown ice at someone in a bar, in order to mock the desperation of the left. It’s entertaining enough for a while but loses steam during the fourth hour of his show, when he’s still flogging it. Eventually, the Georgians start ambling around the studio, checking their phones. One good joke is made today—“The Dems are really going to want to abolish ICE now”—but it’s Robinson who delivers it, and the gag seems to fly over Howie’s head.
Later during the show, a Times investigation breaks detailing the way the Trump family used suspect tax maneuvers to fund young Donald’s inheritance. During a break, Robinson tries to get Howie to pay attention to the story. Howie demurs, finding innovative ways to avoid criticizing the president. “How does the New York Times pass its newspaper down from generation to generation?” he grumbles. Eventually, Robinson manages to address the story on air: “They say that Trump, by the time he was three years old, was making $200,000 a year. That’s pretty good for a three-year-old!”
“Well, you know,” Howie retorts. “There are guys. Guys in the longshoremen’s union, in Boston, who as soon as their son is born, they sign him up for the longshoremen’s union. Even if the kid as an infant isn’t getting paid, he’s at least on the seniority roll. I mean, isn’t that something that’s traditionally done? You try to help out your offspring?”
This is a remarkable evasion from someone who has spent his career slamming the way elites hoard power. Just five pages into his latest book is a conspiracy-corkboard chapter called “Very Fake News” about the incestuous relationship between the political press and the Democratic establishment. In his Reddit AMA last year, he derided the president’s critics in the media as a bunch of “dumb ass-kissers who couldn’t get into law school.”
Now deep into his career, Howie still harbors a sense that while he toils away, the beautiful people are trading favors on easy street. Nancy Shack, Howie’s longtime producer at WRKO, says that his mindset is straightforward: “He hasn’t been given anything; he had to work for everything. This is the driving force for Howie.” So he grinds on, hawking three-for-one book deals and mocking Hillary Clinton in front of live crowds.
But that attitude of cultivated grievance also comes in handy once you have made it on the inside. How else do you keep up the fiction that Trump’s Washington isn’t awash in exactly the cronyism and corruption it promised to eradicate? How else do you change the subject when the president who gave a job to his own daughter gave one to yours, too?
Every day at 3 p.m., Howie’s program begins with a gravelly, steroidal voice-over: “Better strap yourself in. It’s time for the Howie Carr Show.” The voice rumbles on. “Who’s Your Captain?…Who Do You Love?…Unchained and Unstoppable…”
The kicker goes like this: “Rumpswabs, hacks, and moonbats beware. It’s Howie Carrrrr.”
As Howie has said before, it takes one to know one.
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