It was hard to miss real estate tycoon Steven Posner. With his flashy million-dollar diamond watch, dark designer suits, sunglasses, pompadour hairstyle and metal attache case, he looked almost like one of the agents in the film Men in Black.

Typically, you would find him surrounded by an entourage holding business meetings at the bar of one of his favorite hangouts, like the Grill on the Alley in Aventura Mall. Otherwise, he would be indulging in his passions for fast cars and the 44-foot, high-performance boat that brought him to his untimely death last week in a crash with another boat on Biscayne Bay.

Also killed was Clive Warwick, 60, of Aventura, who was a passenger in Posner’s boat, being piloted by Stuart Posner, according to the Florida Fish and Wildlife Convervation Commission. Stuart Posner, Steven’s Posner’s cousin, suffered criical injuries.

Growing up as the eldest son of corporate raider Victor Posner, Steven Posner had a mind that worked like a calculator. He inherited his father’s business acumen, along with a penchant for shrewd dealmaking.

“Steven liked to be a winner,” said Susan Goldman Posner, his estranged widow.

But that’s where the similarities ended. Steven Posner’s top priority was about enjoying life and his family.

Where the father was a recluse in his later years, the son was an outgoing guy who loved entertaining. His circle of friends included many he had known for more than 50 years. His funeral drew a standing-room-only crowd of over 600, including developer Michael Swerdlow, lobbyist Ron Book and businessman Mel Harris. Police shut down Interstate 95 for the funeral procession.

“Some would say my father was one in a billion,” said Dr. Kelly Posner Gerstenhaber, 43, Steven’s daughter and oldest child. “I would argue there never was and never will be again anyone like him. The man epitomized the phrase larger than life. The love that people felt for him is truly remarkable.”

FAMILY MAN

Posner’s three children describe a man who adored his children and five grandchildren. He urged his kids to strike out on their own in business and loved to brag about their accomplishments.

Posner Gerstenhaber is a Columbia University psychiatry professor whose work has set new Food and Drug Administration standards. Jarrett Posner is a New York hedge fund partner and Sean Posner is a Miami real estate executive with the Swerdlow Group.

All three have fond childhood memories of family vacations, tennis matches and weekends in the Hamptons spent with their father.

It’s a far cry from the love-hate relationship Victor Posner had with his children. The patriarch was known for using his vast fortune as a means of control.

“I think he learned a lot from the stuff that happened with his dad,” said Sean Posner, 36, Steven’s youngest child. “He didn’t want to make the same mistakes with his own family.”

Steven Posner’s death at age 67 marks another tragic chapter in the saga of one of South Florida’s high-profile and most controversial families. Victor Posner died in 2002, sparking a major will contest among family members. Steven’s twin sister died in March of cancer, creating another feud after she left the majority of her estate to her Chihuahua, Conchita, and household help rather than her son, Brett Carr.

Steven was going to be a key witness in Carr’s efforts to have her will overturned because, the son contends, she was manipulated into changing it.

“Steven felt Brett should have received the entire proceeds that Victor left to Gail,” said attorney Bruce Katzen, who represents Carr. “He was outraged at what had happened.”

VICTOR THE FATHER

While Gail and Steven were not the closest of siblings, they shared a bond that came from being raised by a man who could be just as ruthless with his family as he was in business.

Gail claimed Victor sexually abused her, leading to a life of substance abuse. Steven Posner spent his life trying to balance his admiration for his father against a desire to be his own person.

Steven and Victor worked side-by-side, first in real estate and then buying up public companies, as early corporate raiders. When they were riding high during the 1980s, they once controlled at least 16 public companies, including DWG Corp. — parent of Arby’s and Royal Crown; Sharon Steel; NVF Co. and Southeastern Public Service Co.

They were among the country’s highest-paid executives, drawing multimillion-dollar paychecks from companies that were often losing money and forced into bankruptcy.

While Victor got most of the credit, those who knew Steven say his creative financial mind and relationships with investment bankers also played a key role in their success. But it also began the unraveling of the father-son relationship.

“He learned from Victor and he took it to another level; He was the power behind the throne,” said attorney Ira Elegant, a friend since early childhood who served as an officer and director of various Posner companies. “Victor was very proud of him at the outset and then he became insanely jealous.”

Like many fathers, Victor had a hard time acknowledging his son’s strengths. It wasn’t unusual for Victor to yell at his son during board meetings, calling him a “moron” or telling him to “shut up.”

“Steven and Victor were two of a kind,” said Jacob “Hank” Sopher, a parking magnate and Victor’s nephew. “They were both very smart and very egotistical. They were always in competition. Steven always thought he could do better than his father. Victor didn’t think he could do as well.”

FATHER-SON SPLIT

At one point, Victor Posner was grooming Steven to take over. Then he changed his mind.

Brenda Nestor Castellano, Victor Posner’s girlfriend and longtime business representative, said Steven was a disappointment to his father. While Victor was a self-made man who dropped out of high school in Baltimore to build low-cost housing, Steven was born into money.

Castellano, who was the main beneficiary of Victor Posner’s will, was at odds with most of Victor Posner’s family during the years leading up to his death. When Victor died, the family accused Castellano of having coerced him into changing his will.

“His father was a very hard worker. He worked seven days a week. Steven’s interests were tennis and boating,” said Castellano. “He was given everything at birth — shares in the company. But it was not enough.”

Those who knew Steven tell a different story. They say the pair’s relationship started to fall apart when the two were sued as part of the landmark Securities and Exchange Commission fraud suit that included Michael Milken and Drexel Burnham Lambert. When the Posners were both barred in 1993 by the SEC from serving as officers or directors of a public company, that marked the end.

“Victor blamed Steven for most of his problems and essentially sent Steven off into the sunset,” Elegant said. “It was definitely not Steven’s fault.”

The pair spent the rest of the 90s locked in a battle over trust money that included multiple lawsuits stretching from Baltimore to Florida. Steven claimed his father had cheated him out of millions of dollars.

Hank Sopher said he had urged Victor to settle with his son and give him the trust money.

“He knew Steven was spoiled; if he gave him the money today, it would be gone tomorrow,” Sopher said. “Victor was a control freak. He was holding Steven and Gail hostage. He wanted to be needed.”

TROUBLED TIMES

During that time, Steven Posner’s lavish lifestyle began catching up with him as a number of creditors sued him for failing to pay his debts. The bayfront apartments he owned at the Jockey Club in North Miami were placed on the auction block several times as the bank foreclosed on the properties.

The Jockey Club apartments were valued at more than $1 million, but Posner owed $1.3 million. By the early 1990s, he had also fallen behind on real estate taxes, income taxes and association fees. He owed hundreds of thousands of dollars in back taxes and faced multiple bank suits that left liens on his properties.

Things turned around after Victor and Steven settled their dispute in spring 2001, the year before Victor Posner’s death.

In a gesture befitting Posner’s brash business style, they agreed to divvy up the assets to be included in Steven’s settlement by flipping a golden dollar coin before a Miami-Dade circuit judge. The crown jewel of Steven’s settlement was a majority interest in a 9.8-acre tract on Hallandale Beach.

Though terms of the settlement weren’t made public, sources said they netted Steven Posner real-estate holdings worth an estimated $100 million. In exchange, Steven gave up any future claim on his father’s estate.

Since the split with his father, Posner’s business dealings were on a different scale. He ran a small office out of North Miami with about a half-dozen employees, but only showed up there sporadically. He invested in small companies, including several in the energy sector. Posner oversaw a real estate portfolio that included about a dozen mostly multi-family properties in Baltimore and South Florida.

Posner’s biggest achievement was the development of the Hallandale Beach property in a partnership with the Related Group and Jorge Perez. They built the Beach Club, three condo towers of nearly 1,300 units, valued at an average of a half-million dollars per unit. The project was largely sold out at the time of the condo collapse.

Perez described Posner as a “straight shooter,” with whom he partnered with for more than a decade.

“You could not have asked for a better partner and a good friend,” Perez said. “He was more of a passive partner. He had a lot of real estate and we developed it for him.”

By handing operations and development over to partners like Perez and others it allowed Posner time to enjoy life.

EXPENSIVE TOYS

Steven Posner’s need for speed and fondness for fast, expensive toys started as a child.

When Steven was about 8, Victor Posner bought him a racehorse dubbed Swift Steve. It set a track record in its first race at Pimlico Race Course in Baltimore.

By the time Steven was 11, the family had moved to South Florida and the son was putting blocks under his dad’s sports car and driving it around Sunset Island, where they lived.

“My dad just couldn’t bear waiting,” Posner Gerstenhaber told the crowd at the funeral about her dad’s childhood driving escapades.

At the time of his death, Steven Posner had a collection of fast boats to go with his luxury cars, including a Lamborghini, a Ferrari and a Rolls Royce.

“Steven did everything in a big way,” said Don Soffer of Turnberry Associates, who has known the Posner family for decades and whose son Jeff sold Steven some of his first boats. “He was very proud of the fact that he had one of the fastest boats on the water. If he saw another boat coming, he liked to challenge them.”

The luxury toys and flashy dress were all part of an image that friends say Steven cultivated in part to compensate for his insecurities. Although the dark glasses seemed like a fashion statement, they were a medical necessity because of his highly light-sensitive eyes.

Steven always traveled with a bodyguard, a practice that dated back to high school when his friend Harris Buchbinder filled the role.

“If Steven was in a particular place, everyone had to know,” said Buchbinder, who met Steven as a teenager and went on to become one his attorneys. “Steven needed to be recognized. He needed a lot of attention.”

But Steven also believed in sharing his wealth with others. He picked up the check most days for his entourage at lunch or dinner. And regularly passed out cigars from his silver attache case.

He was a major supporter of the Diabetes Research Institute, Women of Tomorrow and the University of Miami’s Sylvester Comprehensive Cancer Center. Posner also did things to help friends in need, like paying off a mortgage so someone could keep a house or medical bills.

“He insisted that nobody know,” said Posner Gerstenhaber, who only learned of some of her father’s generosity after his death. “For him it wasn’t about credit. It was about truly wanting to help people.”

WHO GETS WHAT

Steven Posner’s sudden death leaves unanswered questions surrounding his estate, which is likely to be valued at well over the $100 million he received in his 2001 settlement. His children say he didn’t suffer from the market downturns in recent years and made out well on the Hallandale Beach project.

Family members and attorneys say they do not believe Posner had a will, so under Florida law his estate would typically go to his spouse or children. The Posner family is known for its contentious estate battles and Steven Posner’s situation was anything but simple.

Although he had a wife of 44 years, he lived on Williams Island with his longtime girlfriend, Kathryn Chesler, who did not respond to requests for an interview.

The Posners had been separated for at least a dozen years and started divorce proceedings more than once.

The latest divorce filing references a post-nuptial agreement that “settles their property rights, support and maintenance, and other rights and obligations growing out of the marriage.”

In such cases, legal experts say, the wife typically waives any claim on the estate.

“There is a 99 percent chance this estate is going to pass as if he was unmarried,” said Barry Finkel, a Fort Lauderdale family lawyer not affiliated with the case. “A post-nuptial agreement is a legally binding contract, unless the wife claims she was forced to do this or he breached the agreement.”

Posner’s children are optimistic their father’s estate won’t turn into a legal free-for-all like those of their grandfather and aunt. They were part of the many legal challenges against their grandfather’s will.

Posner’s estranged wife, while not saying what she will or won’t do, said the relationship was not quite as “irretrievably broken” as it seemed.

“We were going to get a divorce and he was going to marry someone else, but he changed his mind,” Susan Goldman Posner said. “I spoke to him almost every day. There isn’t a day, we didn’t say ‘I love you.’ It sounds weird, but it was true.”

Miami Herald staff writer Julie Brown contributed to this report.