John Coale, right, and his friend Martin O'Malley, the former Maryland governor, chat in the BWI Marshall general aviation terminal before their flight to Iowa in March on Coale’s private jet. (Jonathan Newton/The Washington Post)

It's late on a Saturday morning, and Martin O'Malley is introducing himself to a few dozen Democrats in the basement of a county courthouse in the nation's first presidential caucus state.

A stocky man in his late 60s paces in the back. He sips coffee. He munches on fruit snacks. He chats up a few people. But he isn’t making introductions, or ensuring that the former Maryland governor sticks to his schedule.

John P. Coale, it turns out, is just along for the ride — a ride that he provided.

A retired, once-flamboyant trial lawyer who made millions off the tobacco wars of the 1990s, Coale is using his private jet to ferry O'Malley around early nominating states as the still largely unknown Democrat weighs a long-shot presidential bid.

In return, Coale, a self-described political junkie, gets a ringside seat.

Coale likes to help his friends. He has an eclectic set of them, both inside politics and out, some of whom he met through his wife, Fox News host Greta Van Susteren.

Since the mid-1990s, according to campaign finance records, Coale has donated more than $750,000 to political candidates and committees, most of them Democratic. But he has also palled around with Republican Sarah Palin. He attended Kim Kardashian’s wedding and represented Lisa Marie Presley in her divorce from Michael Jackson, back when Presley was affiliated with the Church of Scientology, where Coale and Van Susteren have been prominent members for years.

Coale supported his friend John McCain, a Republican, in the 2008 presidential election. But during the primaries, he was a major booster of Democrat Hillary Rodham Clinton, whom he also considers a friend.

Coale was close enough to the Clintons that he spent at least part of the day of the crucial 2008 New Hampshire primary with them in their hotel suite. Siding with O'Malley this time — when Clinton is the overwhelming Democratic favorite — was a calculation based on personal ties.

“I’m committed to Martin,” said Coale, who speaks bluntly and with a trace of the accent of his home town of Baltimore. “He’s the better friend. I’ve known him longer and better.”

Through the years, O’Malley has received more than $77,000 in donations from Coale, including in-kind contributions, as well as a $500,000 loan at the last make-or-break juncture of his political career.

‘I guess I’m the friend’

The two met about 15 years ago, shortly after O’Malley became Baltimore’s mayor. They were introduced by C.A. Dutch Ruppersberger, a congressman from the area and a fraternity brother of Coale’s at the University of Maryland.

At the time, Coale was a legend among trial lawyers, known for his aggressive pursuit of class-action clients and his willingness to take on corporate giants. Besides the tobacco companies, his targets included Union Carbide in the aftermath of the 1984 gas leak in Bhopal, India, that killed thousands; and Imperial Foods, after the deadly 1991 fire at the company’s chicken plant in North Carolina. He sometimes picked cases that supported the Scientology agenda, including a series of lawsuits aimed at the maker and prescribers of Ritalin, the drug widely used to treat attention deficit hyperactivity disorder in children.

In buttoned-down Washington, Coale and Van Susteren rarely discuss their affiliation with Scientology, a controversial religion that opposes psychiatry, preferring spiritual healing as an alternative. Coale said that his religious beliefs don’t drive his politics and that O’Malley “didn’t seem to give a hell” when he told him about them several years ago.

At their initial lunch meeting, Coale and O’Malley hit it off, talking about Johnny Unitas and the Baltimore Colts. Their friendship endured, Coale said, in large part because he doesn’t want anything from O’Malley, who like most politicians is often surrounded by people Coale describes as “on the make.”

“I don’t want a job. I do not want to be ambassador to anything,” Coale said. “There’s nothing — except maybe a state dinner or two.”

And so he tags along on the trail, usually wearing gray slacks and a light-blue oxford shirt with a navy blazer or a navy sweater.

“There is nothing about him that suggests he’s a guy with a yacht or a TV-star wife,” said Ivan A. Schlager, a Washington lawyer who has known Coale for decades. “He’s just a good guy.”

Coale and O’Malley enjoy an easy rapport, talking on their flights about how things are going, rather than focusing on policy issues. Coale, who tends to wander the room when O’Malley speaks, provides intelligence on what he overhears. And they laugh a lot, often about small things, such as the “wild socks” an O’Malley adviser wore on one flight.

“I guess I’m the friend,” Coale said. “You know, most of these guys have a friend. Some people call it the adult on the plane. . . . I validate him. There’s no lack of advice from others.”

In 2006, O'Malley was running for governor against the Republican incumbent, Robert L. Ehrlich Jr., in what remains Maryland's most expensive governor's race. He needed a late infusion of cash, so Coale ponied up $500,000.

O’Malley won, and Coale was soon invited to a small dinner party at the governor’s mansion. When he arrived, he was confronted by Scout, a terrier the first family had adopted from a shelter.

“That dog comes out of nowhere and jumps up and bites me right on the ass,” Coale said. “It actually hurt.”

Scout was eventually banished, after nipping one of O'Malley's sons on the face. The governor's friendship with ­Coale continued.

Coale says his fascination with campaigns is not much different from that of a sports fanatic. “If you’re a big football fan, and one season you get a chance to hang out with the coach of the Packers or something, and the next season it’s the Patriots or whatever, you’re going to do that,” he said.

A more relaxed approach

More than a decade ago, Coale poured his energy into trying to help another Democrat, John F. Kerry, get elected president, reaching out to his vast array of contacts to raise money.

That’s not a role that Coale expects to play for O’Malley. Now 68 and confronting some health problems, he’s taking a more relaxed approach. For the past two years, Coale has successfully battled throat cancer. This week, he’s scheduled for open-heart surgery, an “overhaul” that Coale says should keep him off the trail for a month or so but leave him feeling better than he does now.

He’s happy to lend his plane and introduce O’Malley to some of his influential friends — they had lunch the other day with historian Douglas Brinkley. But Coale’s days of getting on the phone to try to convince other people to give money are largely over.

“I hate it,” he said of raising money. “What I can do to help my friend is fine, but I’m not going to go out and bang on doors or get on the phone that much.”

During O’Malley’s two campaigns for governor, Coale contributed $4,000, the maximum allowed under state law. And as O’Malley has angled toward a White House bid, Coale has given $15,000 to his political action committee, making him one of its larger donors.

But Coale’s biggest contribution has been the use of his six-seater Falcon 100. Between October 2013 and the end of 2014, O’Malley reported 18 plane trips valued at more than $54,000. There have been several more this year.

Federal law does not restrict the amount a donor may give to O’Malley’s PAC, and the free plane rides are considered in-kind contributions. If and when O’Malley formally becomes a presidential candidate — he has said he expects to decide by late May — the rules will change: O’Malley’s campaign will have to reimburse Coale for any flights, at a higher rate.

In late February, Coale flew O'Malley and his aides to a gathering of South Carolina Democrats in Myrtle Beach. The plane was on duty in March for trips to Iowa and New Hampshire. On Wednesday night, it ferried O'Malley back to Iowa.

Last month in Davenport, Iowa, Coale hovered close to O'Malley at a pre-dinner cocktail reception as local Democrats sought to meet their guest speaker. Coale chatted with those who were waiting and was available to keep the conversation going when O'Malley moved on to someone else.

“Hey John, have you met the mayor?” O’Malley called in Coale’s direction at one point, handing off Davenport’s loquacious leader, Bill Gluba.

The next evening, 300 miles away in Council Bluffs, Coale bumped into a familiar face: Iowa's Democratic Party chair, Andy McGuire. "We meet again," she said to Coale. "It seems like we spend every night together."

O'Malley, who's had a side career as a musician, decided to play a song for the crowd in Council Bluffs, using a borrowed guitar. "John Coale, come on close," he yelled out, enlisting his friend's help to move people forward.

Coale says he is better positioned to discuss some issues with O'Malley, 52, than most of O'Malley's staffers, who are much younger. They have discussed O'Malley's return to Baltimore after eight years in Annapolis, for example, and the former governor's decision to locate close to his in-laws.

“John Coale is a smart, savvy, mature sounding board for the governor,” said Colm O’Comartun, a former executive director of the Democratic Governors Association who is close to O’Malley, a former DGA chair. “He provides some comfort and stability and really has no agenda of his own.”

O’Malley said he considers himself “very blessed” by his friendship with Coale, who he said has been “encouraging in every way over these last eight years.”

Departing Annapolis

Coale stopped practicing law after the tobacco windfall, aside from the occasional project — including representing his wife in contract negotiations. The couple shared a law practice before she launched her television career and have lived together since 1980. It is her first marriage and his third. They are big donors to their church and are active in other philanthropies, operating an orphanage in Haiti and adopting two villages in Cambodia.

The couple own a home in Clearwater, Fla., where the church has its central training and retreat center, and they maintain an apartment in New York, a cabin in Vermont and a place in Nantucket, Mass. They spend much of their time in their residences in Washington’s upscale Forest Hills neighborhood and in Annapolis, Maryland’s picturesque waterfront capital, where their 80-foot Trumpy yacht is often moored.

The five-bedroom red-brick home in the Annapolis historic district, which the couple bought in 2010, is on the market for $1.8 million. Coale said there's "a little truth" to the theory that he and Van Susteren saw less reason to stay in the capital once O'Malley left office.

"I don't think I'll be going to the governor's house" now that Republican Larry Hogan has moved in, Coale said. "Don't know Larry. Never met him."

On ABC’s “This Week” in January, Van Susteren described O’Malley as “the big sleeper candidate” of 2016 without disclosing his friendship with her husband — raising eyebrows among some journalists. More recently, on her own show, she made a point of telling viewers about the connection.

While accompanying Van Susteren on a 2008 reporting trip to Georgia, Coale got to know Sarah and Todd Palin, who were in town campaigning for a Republican Senate candidate. Coale learned that the Palins were deeply in debt related to legal investigations in Alaska and helped Sarah Palin set up a political action committee to address it.

He spoke about the PAC with another pal, New York Post gossip columnist Cindy Adams, who promptly mentioned the fund in her column. “Like, within three days,” Coale said, $400,000 was donated.

Coale said O’Malley hasn’t always been thrilled by his choice of allegiances, particularly when Coale supported McCain in 2008 after Clinton lost the Democratic nomination to Barack Obama. During the 2012 presidential race, Coale spent time on the campaign bus of Republican Herman Cain. “It was a hoot,” he said. “The guy’s funny.”

Asked about Coale’s other friends, O’Malley fell back on a line he often uses in other contexts: “I think he’s a broad-minded guy who understands we’re all in this together.”