ST. KITTS—At a beachside picnic table on this Caribbean island, where he lives in voluntary exile, former corporate raider Paul Bilzerian says he hasn't lost his taste for battling his enemies in the U.S. government.

But 25 years after Mr. Bilzerian became a Wall Street felon, the Securities and Exchange Commission is quitting the fight, winding down its quest to collect a $62 million civil judgment against him for securities fraud.

The tally from a court-appointed SEC receiver: about $3.7 million collected, and $8.6 million spent in the effort to collect.

Mr. Bilzerian, 64 years old and his bushy mustache turned white, says he fought to avoid paying because he was wrongly punished. He declines to detail how he worked to protect his money. "That wasn't easy, let me just say that," he says.

To a mention of his bank accounts, he says: "What bank accounts? Do you think I'd be stupid enough to have a bank account?"

His is an extreme example of the challenges, and often failures, financial watchdogs encounter in trying to collect judgments after announcing them with fanfare. Mr. Bilzerian consistently thwarted their efforts, according to a review by The Wall Street Journal of thousands of pages of documents from civil and criminal cases and interviews with people familiar with them.

He appealed legal setbacks, tied up regulators with dozens of lawsuits and motions—often acting as his own lawyer—and used offshore and domestic trusts, partnerships and charities to protect assets for his family. That included assets set aside for son Dan Bilzerian, a social-media star who has attracted millions of online followers by flaunting his exploits with cars, guns, bikini-clad women and high-stakes poker. (See related article.)

The SEC has struggled to collect its penalties more broadly as well. In the three years ended last Sept. 30, the SEC says it collected 42% of the amounts defendants were ordered to pay during those years in fines and disgorgement of ill-gotten gains. That was down from 63% in the prior three-year period.

That record partly reflects limited expertise in the collection process, according to former government lawyers. "Once they get the judgment and the play of the press…they are not really good at enforcement," says Richard Kirby, a former SEC lawyer.

Another former SEC lawyer, John Reed Stark, says, "You can go after more crooks or you can spend your life trying to chase down money from crooks who are devoting their life" to not paying.

SEC officials say they did as much as possible to collect from Mr. Bilzerian, but were prohibited from enforcing the judgment for seven years because of a bankruptcy filing he made. After that, they moved quickly to have him held in contempt of court, officials say.

The SEC says it has a collections unit to seize assets and wages and to contest bankruptcy filings, and has collected on some decades-old judgments. Still, says Enforcement Director Andrew Ceresney, judgments can become uncollectable when defendants die or get jailed or when companies fail.

"We are very aggressive in seeking to collect unpaid debts when assets are available and have a dedicated team of expert litigators exclusively devoted to pursuing debtors," Mr. Ceresney says. "The successes of our collection efforts are unmatched."

The receiver appointed in Mr. Bilzerian's case, Deborah Meshulam, says she is trying to conclude her work by year-end. "We had to fight literally for every penny," she says. And although the cost exceeded the recovery, even counting nearly $400,000 in interest on what was collected, she says the effort was worthwhile because not enforcing judgments undermines the agency's effectiveness.

In Mr. Bilzerian, the SEC faced a foe who stalled it through a range of tactics that one judge labeled "shenanigans" but that to Mr. Bilzerian were legitimate efforts at estate planning and asset protection in the face of government persecution—which he denounces in colorful language.

A high-school dropout, Mr. Bilzerian served in Vietnam and then graduated from Stanford University and Harvard Business School. He burst onto the corporate-takeover scene in the 1980s with hostile bids for companies including Hammermill Paper Co., Cluett Peabody & Co. and Pay 'N Pak Stores Inc., bets that often paid off for him and investment partners when friendlier suitors came in with higher offers. In the case of Singer Co., a Connecticut manufacturer, Mr. Bilzerian took over the company in 1988 and became its chairman.

By then, the SEC had subpoenaed his records in a broad investigation of takeovers and Wall Street trading. In 1988 he faced federal criminal charges of concealing his investments by "parking" stock in someone else's name, not making timely disclosures of his stakes and misstating sources of his funds. Prosecutors said his actions victimized other investors who, left in the dark, sold shares of target companies too cheaply.

Paul Bilzerian, the corporate raider and then-Singer Co. chairman, arrived at New York federal court with his wife Terri Steffen on June 9, 1989, the day he was convicted on nine counts of fraud, conspiracy and making false statements. Associated Press

Mr. Bilzerian was convicted in 1989 of fraud, conspiracy and making false statements to the SEC. He paid a $1.5 million fine and drew a prison sentence initially set at four years, ultimately serving 13 months.

He has long maintained the conviction was wrong, in part because nobody really was injured by his actions.

After his conviction, the SEC sued to force him to give up illicit profits. At a hearing, it expressed concern he was trying to shelter his money. Mr. Bilzerian said he wasn't. The SEC didn't ask for a freeze of his assets but just sought his family's financial records. SEC officials say a judge wouldn't likely have frozen the assets without hard evidence they were being moved around.

So Mr. Bilzerian retained control of his wealth, which he estimated, at the 1989 hearing, at more than $50 million. In a private suit later that year, he put his net worth at $81.4 million. At times, he has said he made hundreds of millions of dollars.

A judge in the SEC civil suit found him liable for securities fraud in 1991. Mr. Bilzerian and his wife then transferred property in Tampa, Fla., where they were building a mansion to just her name.

Three months after that, Mr. Bilzerian filed for bankruptcy. He said he had suffered large losses on Singer.

Years of legal skirmishes followed.

In 1993, the SEC obtained orders for Mr. Bilzerian to pay $62 million. That included disgorgement of up to $12 million of his profits, plus his partners' profits and interest.

Mr. Bilzerian said that after he was in bankruptcy, the SEC judgment should have been dropped, since its purpose was to return ill-gotten assets and he no longer had any significant assets. He also said any debt to the SEC should have been discharged in his bankruptcy. Although these arguments didn't prevail, bankruptcy-related litigation stalled the SEC's effort to collect for years.

"I think he was a little smarter than those who were trying to pursue him," says James Orr, the bankruptcy trustee.

Judith Starr, a former SEC lawyer, says that when she took over the case for the agency in the mid-1990s, she was alarmed at how little progress had been made. "I was pretty concerned that we were getting judgments and just putting them on the wall," she says.

Researching records, Ms. Starr says, she found a network of trusts, partnerships and corporations in the U.S., the Cook Islands, the Cayman Islands and elsewhere formed by Mr. Bilzerian or his wife. Properties once in their names were transferred to such entities.

Mr. Bilzerian says most of those transfers were based on legal advice to his wife on how to protect assets she held after his bankruptcy for their children. He says the advice made the assets vulnerable to seizure because he was listed as a trust beneficiary. His wife, Terri Steffen, says the government had characterized it as "sneaky…and that wasn't it at all."

In a court filing in December 1998, Mr. Bilzerian said he had no assets "other than used clothing, a used Casio watch, and the like."

That year, a Utah software company of which he was president spent $120,000 for Mr. Bilzerian's services, but paid it to a holding company he ran rather than directly to him, a judge later wrote.

The Tampa mansion Paul Bilzerian once called his 'Taj Mahal' became a flashpoint in his fight with the Securities and Exchange Commission. When his wife agreed to sell it in a settlement with regulators, Mr. Bilzerian helped arrange for acquaintances and relatives to purchase it, allowing his family to stay. Tampa Bay Times/Zuma Press

Mr. Bilzerian's family's home was the Tampa mansion—28,000 square feet with an indoor basketball court and guesthouse, abutting two lakes.

The property's owner, by then, was a Nevada partnership, which in turn was owned by a Cook Islands trust. In late 1998, the parents of Mr. Bilzerian's wife became the trustees, and she the sole beneficiary of the trust.

Mr. Bilzerian didn't hide his distaste for paying the SEC. "I have no reason," he said at a 1999 federal-court hearing, "to dedicate the rest of my life to trying to earn money all of which would go to basically pay a judgment that I don't believe…should have been entered in the first place."

He was more emphatic at the beachside interview in St. Kitts this year. "Look…the government hates me. I get it," he said. "I despise the people in the government. We despise each other."

He added: "I would rather starve to death than earn a dollar to feed myself and pay the government a penny of it."

In 2000, a federal judge in Washington found Mr. Bilzerian in contempt of court, saying he had "made no attempt whatsoever to pay the judgment." At the SEC's request, the judge appointed a receiver to pursue Mr. Bilzerian's assets. He later ordered Mr. Bilzerian to jail until he "purged" the contempt by showing he was no longer trying to avoid paying the judgment.

The SEC receiver expressed frustration at tactics that she said included replacing trustees when information was requested from them. "The Bilzerian family shuffles the deck chairs every time an asset appears to be within reach of the SEC," said Deborah Israel, a lawyer for the receiver, at a 2001 hearing.

Mr. Bilzerian kept the SEC and court up to date on the balance in his prison commissary account. It was 80 cents, he reported in June 2001. Three months later, he said it was 23 cents.

Seeking information, the Federal Bureau of Investigation raided the Tampa mansion, and scoured the trash outside the house. The SEC and receiver listened to tapes of Mr. Bilzerian's prison calls.

The ownership of the mansion often shifted, though not the Bilzerians' occupancy. A list of the shifts shows what the SEC was up against.

Watch a video explainer about the Bilzerians and the Tampa mansion.

Mr. Bilzerian's wife, Ms. Steffen, made a deal in 2002, opposed by her husband, to spring him from jail. She agreed to have the partnership sell the mansion and split the proceeds with the receiver, plus turn over some securities and cash.

When the mansion sold in 2004, for $2.55 million, the buyer was another partnership. This one was controlled partly by the mother of a next-door neighbor. Mr. Bilzerian helped put together the deal.

Among the other partners was a corporation controlled by Mr. Bilzerian's wife's parents. Their involvement remained unknown to the SEC for at least two years.

The in-laws were majority partners, holding a 99% interest, at first through the corporation and then through a trust. Mr. Bilzerian's sons were named as trust beneficiaries.

In 2006, amid a dispute between the Bilzerians and the neighbor's mother, a state judge called the couple "at best…trespassers or squatters" and ordered them to leave the property. But they stayed after the partnership went into bankruptcy and the house was sold to a firm that was run by another Bilzerian acquaintance.

That firm made its purchase with financing help from a Bermuda charity, Puma Foundation Ltd., named for a Bilzerian family cat.

Just before the sale closed, a trust controlled by Mr. Bilzerian's mother-in-law acquired a majority interest in the purchasing firm. The firm paid his wife to manage the property.

The acquaintance who previously owned this purchasing firm didn't return a call seeking comment. The mother of the neighbor declined to comment. Mr. Bilzerian's father-in-law is dead. His mother-in-law, Lois Steffen, says she recalls little about the transactions. "I was a very silent partner," she says.

The Internal Revenue Service's criminal division has examined Mr. Bilzerian's involvement in the sales of the house, say people familiar with the probe. The IRS declines to confirm or deny that. No charges have been filed.

Paul Bilzerian's older son, 33-year-old Dan, may have overtaken his father's renown, largely through social-media posts about his exploits with women, gambling and guns that have gained him more than 4.5 million Instagram followers. David Walter Banks for The Wall Street Journal

This spring, a bank purchased the mansion at a foreclosure auction. Amid the foreclosure proceedings last year, Ms. Steffen and other family members were ordered out. Mr. Bilzerian says he had already left for St. Kitts, and his wife followed.

On St. Kitts, they live in a condo they say is owned by their younger son, 31-year-old Adam, who obtained citizenship there in 2007. He renounced his U.S. citizenship and later wrote a book titled "America: Love it or Leave It—So I Left." Adam, who like his brother Dan is a professional gambler, currently spends much of his time in the U.S.; he didn't respond to requests for comment.

Dan Bilzerian might now be the highest-profile member of the family, thanks to social-media accounts of his antics in Las Vegas and Hollywood.

Paul Bilzerian in recent years has been engaged in business dealings with his sons. In one, he and Adam have been involved with a company described by its website as marketing real estate and helping people who want to participate in St. Kitts and Nevis's "citizenship-by-investment" program.

Mr. Bilzerian leads a lifestyle far removed from his days as a corporate raider. He often dresses in tennis attire and a baseball cap, and rides around in a golf cart. As he has since he was young, he eschews alcohol, coffee and anything that might impair his faculties. For months last year when his wife was in the U.S., he says, he didn't leave a small tourist strip, living on lettuce, tomatoes and cucumbers.

In the end, both Mr. Bilzerian and Ms. Steffen say, no matter how much went uncollected, the government won by destroying their lives over a quarter-century. "We lost, and we lost everything," she says.

Mr. Bilzerian says that if he could do it over, he would capitulate to the government, because he sees how the fight devastated his family.

Paul Bilzerian and his wife Terri Steffen earlier this year in Frigate Bay, St. Kitts, where they live in a condominium owned by their son Adam. Michael Rothfeld/The Wall Street Journal

Still, since he can't rewrite the past, he says he is thinking of filing another motion to undo the SEC judgment and "starting it up again."

"I've been thinking about it for a while. Why not take another round at it?" he says.

Write to Michael Rothfeld at michael.rothfeld@wsj.com and Brad Reagan at brad.reagan@wsj.com