My session with Dr. Phil had reached an impasse.

About three hours in, seated inside the Dallas mega-mansion where he is steering his herky-jerk transition from daytime TV behemoth to MAGA-friendly newsman, the once-licensed psychologist was giving no ground on what seemed to me an obvious point.

“I don’t think I’m qualified to talk about politics,” he said, steepling his fingers in contemplation. And so, he insisted, he really hadn’t.

This was difficult to square with recent events.

In the last two years, Dr. Phil (surname: McGraw) had ended his flagship talk show and created his own news and entertainment network, trafficking daily in conservative-coded subjects — “Dr. Phil: The Hidden Gem in Trump’s ‘Big Beautiful Bill,’” “Dr. Phil Investigates: Are Schools Secretly Transitioning Your Child?” — in an unswerving crusade against “the woke left.”

He had spoken glowingly of President Trump as an invited guest at Mr. Trump’s Madison Square Garden campaign rally, at a White House faith event and at a recent Texas flood briefing, where the president interrupted himself after spotting Dr. Phil — “There’s Dr. Phil. Look at Dr. Phil. You’re looking good, Phil. This is a hell of a situation, isn’t it?” — and later asked him to address the bereaved.

Most strikingly, Dr. Phil had secured intimate access to embed with a camera crew on Immigration and Customs Enforcement raids, pledging to agents that his broadcasting aim was to “tell your story and have your back.”

Dr. Phil likes to say that his focus is social and cultural issues and always has been, since his Oprah-ordained rise as a tough-loving public mediator of family dramas. It is the politicians, he says, who have lurched into his lane, not the other way around.

He does not care about the Federal Reserve, he noted, with a merry profanity. He does not understand the mechanics of legislation.

That was more policy than politics, I suggested.

“I don’t know!” he said. “You’re making my point.”

And his macro point was this: “I’ve spent so much of my life focused on why people do what they do,” Dr. Phil said, by way of mission statement, “and don’t do what they don’t do.”

In recent months, friends, detractors and former associates have wondered often why Dr. Phil is doing what he is doing — barreling into partisan media after a lucrative career as a big-tent hitmaker — and why he is not doing what he is not doing: recognizing that he has barreled into partisan media.

What is beyond debate is that Dr. Phil, 74, has exposed his shrink-next-door reputation to the whims of a fractured, fractious media ecosystem quite unlike the one he conquered.

It has already been messy. Last month, his company, Merit Street Media, filed for bankruptcy in a hail of litigation involving its faith-based partner, Trinity Broadcasting Network. (Dr. Phil swiftly announced a new venture with similar ambitions, Envoy Media, and has begun producing content under its banner.)

Yet whatever his professional fortunes, Dr. Phil has emerged once more as an avatar of his times, a drawling testament to the commingling of entertainment and civic life.

The president, his acquaintance of two decades, is a fellow network television stalwart of the early 2000s. The Department of Homeland Security has mulled a reality show for immigrants to compete for citizenship.

Can it really be said that Dr. Phil looks out of place, lumbering on a balky knee beside federal authorities, making “Cops”-style television out of early-morning ICE arrests?

“With so much fake news circulating about the work ICE agents do, we’re grateful for those like Dr. Phil who are willing to share the truth,” Tom Homan, the president’s border czar, said in a statement sent by the White House. The two have regularly shared the screen.

Still an advocate, he says, for legal immigration and gay rights, Dr. Phil believes he has nonetheless lost friends from his bygone life in Beverly Hills, Calif., where he keeps a home.

He has faced death threats, he said — there was little of that in daytime. (He attributed this largely to his stands against antisemitism.) He has failed publicly as never before, after a long talk-show reign at No. 1, for the high privilege of clawing into the living algorithm of ubiquitous news chatter.

“I don’t have to be doing this at all,” he noted. “This is not a got-to job. This is a get-to job.”

But then, people are complicated — “Dr. Phil” proved this every weekday — and during our four-hour visit last month, Dr. Phil took care to project that he is, too.

He is a self-described “old country boy from Texas and Oklahoma” whose Dallas home includes glimmering door handles fashioned into a lower-case “d” and “p,” a boulder-size Lego wall installation depicting scenes and characters from his life, “seven or eight” fireplaces, a Banksy, a coffee-table book about maximalism and a decorative rooster of unknown provenance.

“There’s something special about it,” he said, sighing a bit, during a mostly affectless tour of the space. “I don’t know what it is.”

He is known to keep two essential items in the trunk of his Rolls-Royce: a shotgun and a tennis bag. “You never know,” he reasoned.

He considers himself a journalist (“You think I’m overqualified?”) and does not dwell on why ICE has furnished him with premium access. “We’ve asked for it,” he said bluntly.

He has a face so recognizable from his old career — the sheriff-grade mustache, the furrowed helipad of a forehead — that it can shadow his newer one.

“You’re Dr. Phil,” a Thai immigrant told Dr. Phil, mid-arrest, last January in Chicago. The host had been questioning the man, whom authorities accused of sexual misconduct, beside Mr. Homan.

“How do you know me?” Dr. Phil asked.

“I’ve seen Dr. Phil on TV.”

Dr. Phil looked almost resigned.

“Yeah.”

Becoming ‘Dr. Phil’

In many ways, Dr. Phil’s arc is the story of America’s last three decades of media, celebrity, politics and media-celebrity-politics.

If anything, he was the more prolific TV frontman than Mr. Trump, the truer bootstraps story, the host with his wagging finger on the pulse of the great American middle.

With a few tweaks to the wayback machine of modern politics, is it so impossible to imagine Dr. Phil as the high officeholder — certainly friends and strangers prodded him through the years — and Mr. Trump as the fading media giant whose new venture just went bust?

“He is and always has been inevitable,” Rachael Ray, a talk-show contemporary, said of Dr. Phil. “He understands the concept that you are here to serve your audience.”

Dr. Phil’s public journey began, inadvertently, before an audience of one: the most famous civil defendant in daytime.

Raised across Oklahoma, Colorado and Kansas — his hard-drinking father was an oil-rig equipment supplier before he pursued a psychology career — Dr. Phil worked initially as a psychologist himself. He later co-founded a trial preparation consultancy, attracting high-profile clients, including Exxon, after the 1989 Exxon Valdez oil spill, and eventually, fatefully, Oprah Winfrey.

She hired him after Texas cattlemen sued over a 1996 episode about mad cow disease. After the trial, Ms. Winfrey was so taken with Dr. Phil’s pitiless charm and boundless aphorisms (“It may not be fair but it is,” “Winners do things losers don’t want to do”) that she made him an on-air regular.

By 2002, he had his own show, entrenching himself firmly in the zeitgeist of the new millennium. He hosted quarreling couples, unruly teens, a sitting president and first lady (George W. and Laura Bush) and a go-to financial guru and future senator named Elizabeth Warren.

“I figured out really early on: You better listen to your audience and meet them where they are,” Dr. Phil said, “instead of asking them to meet you where you are.”

He enshrined himself — alongside Dr. Mehmet Oz, now Mr. Trump’s overseer of Medicare and Medicaid — as part of an Oprah-branded constellation whose emphasis on health and wellness seemed to partly presage the Make America Healthy Again movement. (A representative for Ms. Winfrey did not respond to messages.)

While Dr. Phil was sometimes criticized for unseemly voyeurism or reductive counsel, there was evidence that his show did some good. A 2016 study suggested that devoted “Dr. Phil” viewers were likelier to seek mental health treatment.

As with much of daytime television, including Ms. Winfrey’s show, the moment of peak cultural primacy passed. Ratings sagged. A 2022 BuzzFeed News article described a “toxic workplace” at “Dr. Phil.” A 2017 investigation by STAT and The Boston Globe reported that the program sometimes exploited and endangered people with addiction problems. (The show denied this.)

Beyond the Paramount lot where he filmed in Hollywood, Dr. Phil hinted at broader interests. In public appearances, he defended trans people and backed gun reform measures after mass shootings. He dissected white privilege on “The Breakfast Club” radio show.

He started a podcast (“Phil in the Blanks”) in 2019. He appraised Mr. Trump, sometimes critically, on late-night television.

“I can’t diagnose him because I haven’t done proper evaluations,” Dr. Phil told Jimmy Kimmel mischievously during the president’s first term. But “certain personality disorders” came to mind.

When Covid hit, Dr. Phil seemed to find more common cause with the political right, chastising authorities over school lockdowns. “I was labeled a nut,” he told Robert F. Kennedy Jr., now Mr. Trump’s health secretary, during an affectionate televised forum last spring.

“Dr. Phil” ended in 2023 — of his volition, he has said. Friends encouraged his new explorations.

“We know you’re apolitical,” Bill Maher told him, with an exaggerated wink, on a podcast last year.

By then, Dr. Phil had produced a new book, “We’ve Got Issues,” pitched directly at the culture wars. He lamented a country that “can’t stand success” and cowered before “the tyranny of the fringe”: those who believe that “every white person is a racist,” that anyone concerned with youth gender identity “is a hateful transphobe,” that every gun owner “is an advocate of violence.”

He referred to “cancel culture,” or variations of it, nearly four dozen times.

Hoping to sharpen his book’s arguments, Dr. Phil enlisted Jeff Nussbaum, a longtime speechwriter for former President Joseph R. Biden Jr., as a Democratic foil.

“I took pride in being a sparring partner,” Mr. Nussbaum said, “though recent events seem to show that either I lost or he moved to a different ring.”

The Doctor and the President

In June 2024, Merit Street Media secured a major get: the presumptive Republican nominee, hosting Dr. Phil at Mar-a-Lago.

“You’ve always been very special,” Mr. Trump told him.

The interview, one month before Mr. Trump was shot in Butler, Pa., is a remarkable rewatch — and a prime example of what can often impress Mr. Trump most: He prizes people who succeed on television. Staring at the face of TV psychology, he seemed compelled to take advantage.

And so, Mr. Trump, rarely prone to introspection or therapist-speak, observed that he had “a very good disposition for trauma.” He spoke openly about his tendency to suppress stress.

“You’re sort of being my psychiatrist,” Mr. Trump said. “Maybe I could use a psychiatrist.”

Dr. Phil urged Mr. Trump against governing vengefully if elected. (Asked in our interview if the president listened, Dr. Phil said, “I mean, he hasn’t locked anybody up.” The same day, Mr. Trump baselessly accused former President Barack Obama of treason and said it was “time to go after people.”)

But with an online audience of millions, the sit-down fulfilled an early Merit aspiration: demonstrating Dr. Phil’s range.

“Phil has an intuitive ability to read the national culture,” said Ken Solomon, a longtime friend and tennis partner who became Merit TV’s chief executive. The daytime show, Mr. Solomon added, “was narrow compared to his overall expertise.”

TV veterans like Steve Harvey and Nancy Grace joined the roster. The Professional Bull Riders league signed on. Executives outlined plans to reach more than 100 million homes, even as some in Dr. Phil’s orbit clocked the overstuffed media landscape.

“Starting a start-up in this climate in entertainment is just next to impossible,” said Harvey Levin, the TMZ co-founder, who is friendly with Dr. Phil. “When I heard he was doing that — boy.”

Merit recruited a team of more than 100 to the Fort Worth area to work from its five-acre studio, where Dr. Phil often arrived by helicopter. His stated goal was to “own the debate lane.”

But quickly, employees said, the preferred contours of that debate became clear. Guest bookings tilted decidedly right. Dr. Phil warned viewers that “illegal immigrants are fueling crime across America.” He enthused over what he considered agreeable conditions for immigrant detainees. “You said there are even exercise classes for the women,” he nudged Mr. Homan amid raids in Los Angeles.

Activists scorned him as a tool of the state.

“When you are riding along with the government, they are putting you on a publicity tour,” Alida Garcia, an organizer and former immigration official under Mr. Biden, said in an interview. “He is participating as basically a propaganda machine for ICE.”

Producers whom Dr. Phil’s team made available for this article said he cared only about following the facts. “If it’s towards one side more than the other,” one producer, Justin Arluck, said, “that’s where the facts are.”

Asked if he had been aware of other employees’ concerns about political material, Dr. Phil paused for a beat. “They certainly should not be expected to be involved with it if it’s not something they can passionately commit to,” he said.

Dr. Phil’s appearance at Mr. Trump’s rally last fall seemed to signal his political intentions, though he suggests this was largely an accident.

He has said he would have also appeared with then-Vice President Kamala Harris, claiming that her camp failed to follow up after some initial discussions. Several senior Harris campaign aides said they were unaware of any such dialogue.

Mr. Solomon, the close friend and a longtime Democratic fund-raiser, said he and Dr. Phil had “a difference of opinion” on the Trump event. “I said, ‘Well, if you just do the one, people are going to come to the conclusion that they have come to,’” Mr. Solomon recalled.

That conclusion still appears to bother Dr. Phil. He declined to say if he even voted for Mr. Trump despite his cameo at Madison Square Garden.

“When people ask me about that, I ask them if they’ve listened to what I said,” he said. “Did you?”

I said I could understand why those watching him at the Trump rally, where chants of “Dr. Phil!” echoed, concluded that he was probably voting for Mr. Trump.

“They have impeached him, indicted him, raided him, railroaded him, shot him and sued him,” Dr. Phil told the arena. “And where is he? He is still standing.”

Dr. Phil also plugged his network, celebrated the First Amendment and did not explicitly endorse the candidate. If other guests slung maximally red meat — labeling Ms. Harris “the Antichrist,” smearing Puerto Rico — his offering might fairly be classified as medium-rare.

“I was with Trump during his MSG speech and remember it was pretty lukewarm,” Tucker Carlson, another rally speaker, said of Dr. Phil in a text message.

He added that he had never watched Merit.

“Nothing against Dr. Phil,” Mr. Carlson said. “I just hate all television.”

Walking the MAGA Line

This wider reaction to Dr. Phil’s rally appearance — searing liberal disdain, mild conservative gratitude — was instructive.

He was MAGA-affiliated but not quite MAGA. He was in the room but not of it.

Merit’s ratings seemed to reflect its neither-fish-nor-fowl status, placing the network fathoms behind not only established competitors like Fox News but also relative upstarts like Newsmax and NewsNation. (Dr. Phil’s team insists Merit was gathering momentum, citing encouraging viewership figures on Inauguration Day.)

Some employees had hoped that Mr. Trump’s return, and his nominal closeness with Dr. Phil, might boost the business.

In March, Merit occupied the “new media” seat in the White House briefing room. In May, the president praised Dr. Phil and Merit from the Rose Garden. (Dr. Phil attended in his capacity as an appointee to a federal committee on religious liberty.)

But the company was wobbling. Last month, Merit filed for bankruptcy and accused its partner, Trinity Broadcasting Network, of reneging on commitments. (Trinity did not respond to messages seeking comment.)

Professional Bull Riders, moving to recoup roughly $180 million from its media rights deal, has also joined the legal morass. Merit has made counterclaims.

The dispute seems to have dented Dr. Phil’s standing in some corners of his former city.

“He stopped paying us and tried to tear up and walk away from his contractual commitment simply because he had a change of heart,” said Mark Shapiro, a top associate of the Hollywood super-executive Ari Emanuel and the president of TKO, which owns Professional Bull Riders. “I’ve really never seen anything like it.”

None of this has stopped Dr. Phil from announcing a breakaway venture, Envoy Media, for which loyalists are preparing a new studio space in Irving, Tex., that previously housed a Spanish-language TV company.

In our interview, Dr. Phil hailed Envoy’s “disruptive” potential, sprinkling in buzz-phrases like “citizen journalism platform” and “interactive app.”

Retirement does not appear to have occurred to him.

“This is not what I do. It’s who I am,” he said. “And I’m not sure that that’s always healthy.”

Certainly there are other ways to spend his time. Dr. Phil has been married to his wife, Robin McGraw, with whom he has two adult children, for nearly five decades.

His outdoor tennis court includes misters to counteract the Dallas heat. A whirring staff minds the grounds and hands him unsweetened iced teas. He is quick to attribute the home’s trimmings to Mrs. McGraw, describing their prodigious collection of art and light fixtures so dryly that it can be difficult to tell when he is joking:

“Everybody needs winged lightbulbs.”

“Every one of those pieces of glass was put up individually by these people from Czechoslovakia, if you can imagine.”

Such are the spoils of an uncommon American life — and a reminder, those who know him say, of why Dr. Phil might do the things he does.

“He really is a sort of Horatio Alger story and really believed strongly that anyone could take a similar path,” said Mr. Nussbaum, the former Biden aide who helped with his book. “That’s the genesis of his advice-giving.”

While some Democrats have accused Dr. Phil of pandering, many of his present views appear sincerely felt. He is, friends noted, an affluent septuagenarian Texan whose beliefs broadly reflect his peer group’s.

In one recent video, Dr. Phil covered what he saw as an outsize backlash against another Texan, Beyoncé, for wearing a shirt considered insensitive to Native Americans.

When, he wondered, did intentions stop mattering? What happened to critical thinking?

“Hell hath no fury,” he told viewers, “like the woke left finding a new celebrity to cancel.”

As we sat in his home office, with a large rendering of the “Hollywood” sign behind him and a backpack from the Bel-Air Country Club on the desk, I asked if he ever felt as though the line applied to him.

He almost smirked.

“Yeah.”

Audio produced by Sarah Diamond.

Kitty Bennett contributed research.