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The road to a Suffolk Downs casino has been longer and a good deal more difficult than developer Richard Fields had expected, but at least nobody has been shot this time.

Not like the last time, in Florida, when the attempted assassination of a tribal lawyer working with him marked a low point of Fields’s nine-year odyssey, ultimately successful, to develop Hard Rock casinos with the Seminoles.

But the path to a Boston gambling resort has been its own exhausting grind. While Suffolk Downs was locked in protracted negotiations with the city, swaggering Vegas mogul Steve Wynn parachuted into Everett at the 11th hour and now threatens to snatch away the casino license for which Fields and his partners have labored for years.

The fate of the last thoroughbred track in New England rides largely on the 67-year-old Fields, the track’s charismatic public face and largest shareholder, who brings an “almost irrational confidence” in the future, according to one partner, as well as one of the oddest résumés in the gambling business. Or any business.

He was plucked, as if from nowhere, by Donald Trump as the original “apprentice,” and later battled his mentor as a rival, earning enormous wealth in a career that evolved from talent manager and nightclub owner to land developer and gambling magnate. Now the working-class kid from the Bronx splits his time betweenNew York City, Miami, and Boston, and pals around with superstars. His $175 million Wyoming ranch was featured in Forbes.

The city boy who inexplicably wanted to be a cowboy has befriended singer Willie Nelson, joined the board of Nelson’s charity, Farm Aid, and once gave Willie a lovable mule named Wilhelmina. Or so says Willie Nelson. “I don’t know where in the hell the mule come from but I’m glad he had her because she’s a great friend and a good pet,” Nelson said in a phone interview. “And I ride her and talk to her a lot.”

As a storyteller, Fields is jocular and animated, until the topic turns to the money-losing, Depression-era racetrack he owns with partners in East Boston. He speaks with reverence for “this special place.” On the opening day of racing season in June, “I felt like the father of the bride,” Fields said in a recent interview at the track. “I feel a tremendous emotional connection to this place.”

Uninterrupted, Fields will go on and on about the land and his plans to plant gardens at Suffolk, until he sounds like a flower child talking about, like, the earth, man. “I believe part of what we need to do in this country is reconnect people with the earth,” said Fields. “People don’t know where the food is coming from. That’s another conversation that can go for a long time.”

In the realm of business, Fields seems unsentimental and litigious, having sued and been sued over disputes as important as a multimillion-dollar casino business and as trivial as a fur coat. Spooked by the unsolved shooting of Seminole lawyer Jim Shore in 2002, and claiming to have received death threats, Fields ordered three customized armored cars for himself and his family, according to court papers. He insisted on cars that could “withstand an assassination attempt by skilled marksmen firing multiple rounds from automatic weapons at close range.” And when the cars seemed unfit to repel such an attack, he sued.

But Fields pushes back against the notion that he is a quick draw with a lawyer in his holster. “All I want to do is ask the people to do the right thing,” he said. “All you want them to say is, ‘Jeez, I’m sorry.’

“I don’t think I’m quick to sue; I really don’t,” he said. Then in perfect deadpan: “I’m going to give you a chance on this story to write the right thing and if you don’t, then we’ll have to talk about it.”

As rich as he is, Fields has lots of stories from childhood to prove he hasn’t forgotten where he came from. His mom was a housewife, his father a self-taught artist.

“You had an intact family and nobody realized that you didn’t have any money,” said Fields. “Nobody had any money!” Not long ago, Fields brought his mother, now 89, to visit the old neighborhood in the Bronx. “And she says to me, ‘You know, when we lived here your father made $35 a week.’ Thirty-five dollars a week!”

More than 50 years later, Fields is a philanthropist who has given away millions to children’s causes, medical research, agriculture, and law enforcement. “It’s hard for me to say no,” he said, “as anybody who knows me will tell you.”

Jim Marley, somebody from the old neighborhood who knew Fields “when he was just a nobody,” has often tapped his friend for money for local causes. Now 70, Marley is assistant executive director for Bronx community-based programs for Good Shepherd Services.

Their relationship dates to about 1981, when a friend put Marley in touch with Fields for help raising cash for neighborhood programs. Fields didn’t have crazy money back then, but he had crazy ideas: He connected Marley with a writer who wrote Marley’s life into a screenplay, which Fields thought they could sell to raise money.

“It never went anywhere,” Marley said. “I saw it once. They made me Italian. And a chef.”

Not long after, when a Bronx homeless shelter was about to miss its payroll, a desperate Marley tried Fields again. “I need $1,200 in the next four hours,” he remembers telling him. Fields wrote a check. The agency was saved. Over the next three decades, Fields quietly helped other people or programs in crisis, Marley said.

Marley recalls Fields visiting at Christmas when neighborhood children in the programs received gifts. “And so in the first room, he’d be like weepy almost. By the sixth room he’d be back on his cellphone. He has the attention of a gnat. But he was absolutely dependable. He has never forgotten being a kid in the Bronx — ever.”

Fields started out in the entertainment industry. Then, around 1980, he became a partner in a series of nightclubs, called Catch a Rising Star. He managed entertainers, such as actress Marla Maples, who married and split from Donald Trump in one of the juiciest tabloid dramas of the 1990s.

His partner at the time, Rick Newman, describes Fields as a “deal junkie,” enthralled with negotiations and expanding the business. “Like a marriage, we had our clashes, but they were minimal compared to our successes,” said Newman. “He can be as charming as anyone.”

In the early 1990s, while Fields was accompanying client Joy Behar, now of “The View,’’ on a shoot for a pilot, he received a cold call from Trump, who had heard about the pilot and wanted to talk about it. At first, Fields suspected a prank. A cold call from Donald Trump? “I thought my friends were kidding me,” Fields admitted. “When I came back to New York, we talked and became fast friends.” Trump hired Fields as a consultant.

Fields happily calls himself “the original apprentice,” and gives Trump credit for changing his career. It was at Trump’s recommendation that Fields left the entertainment business for development. “His instincts were right,” Fields said of his mentor. “He can pick talent.”

Their bromance eventually soured, and by 2004 they were locked in litigation over Fields’s deal to develop casinos with the Seminoles. Trump accused Fields of cutting him out of the deal and misleading the tribe. Fields claimed he only pursued the project after Trump passed on it.

In hindsight, Fields says, the fight never should have happened. “There were a lot of mutual friends who tried to intervene,” he said. “But Donald felt wronged and it took a while to work it out.” They have since made up. “I’m very fond of him. We have a good relationship.”

Trump confirmed in a recent Globe interview that he, too, is over the fight, indicating that he was on the better end of the settlement. “It’s amazing how that can make you nice,” Trump said. “But that was OK. No, we had a dispute that was settled very amicably. I do speak with him. We had lunch recently. Very good guy. Very professional.”

Fields’s current fight cannot be settled with a handshake. To survive as a horse track, Suffolk Downs must win the Greater Boston resort casino license, over Wynn and a Foxwoods project in Milford. By the time the license is awarded in 2014, Fields will have spent almost as much time at Suffolk Downs as he did developing the Hard Rock casinos in Florida.

“These things take a long time to do,” said Fields, who is married and has grown children. “You can’t just show up one day and go, ‘OK, I’m going to build this.’ ”

Of course, showing up one day is exactly what Wynn did in Everett, but Fields won’t yield the point.

“You just can’t,” he repeated. “I wish that you could, because this has been so painful.”