Big-Time Financier David Sugarman Falls Far, Ends Up in Jail
Illustration by Allen Douglas / allendouglasstudio.com

Big-Time Financier David Sugarman Falls Far, Ends Up in Jail

In a gilded, colonial-style home in Millstone Township, New Jersey, Mary nestled peacefully on her living-room couch. Fast asleep, the 35-year-old pregnant brunette didn't hear her boyfriend drunkenly stumble in.

Mary, a brown-eyed, five-foot-five former model from Bronxville, New York, and her boyfriend of nine months, David Sugarman, had recently moved into the $1 million, 4,800-square-foot house. It was filled with winding, carpeted staircases and decadent crystal chandeliers. The house was 43 miles from Manhattan, where Sugarman — a charming, baby-blue-eyed, Jewish 39-year-old from Marlboro, New Jersey — had started his career as a Wall Street investment banker nearly two decades earlier.

Sugarman staggered into the house through the front door. He reeked of booze and sweat. Seeing Mary on the couch, he moved toward her. Suddenly, he grabbed the base of the couch and flipped it, launching Mary to the ground.

Dazed and disoriented, Mary scrambled to her feet and whimpered, "What are you doing?" but even as she stared into his glassy eyes, Sugarman didn't respond. Instead, he shuffled a few steps across the room and snatched a phone charger. He wrapped his fingers around the long white cable and lunged toward Mary. She shrieked, but there was no time to back away. The wire was wrapped around her neck.

Mary flailed wildly as she tried to resist his assault, but rather than releasing his grip, Sugarman elbowed her in the belly. Wracked with pain and fear for their unborn child, Mary broke away and charged toward the front door. She jumped into her car, locked the doors, and frantically dialed the phone number of Sugarman's father, Allan. With every ring, her heart pounded, knowing her attacker was near.

Finally, there was an answer. "Your son is drunk," Mary said, panting. "Can you come here?"

"Right away," Allan Sugarman responded.

But the relief was short-lived. Seconds later, Mary received a stream of texts from David, urging her to come back inside the house. "You'll be safe here," he claimed. But Mary knew better. She shot back a quick text to let him know his dad was on the way.

Sugarman, not wanting to face his father, quickly left.

Minutes later, Allan pulled into the driveway, but as he walked toward Mary's vehicle, David returned, angrier than ever. What happened next is a blur. Allan tried to calm his son's rage, but his efforts to snap David out of his drunken trance only escalated his aggression. A few punches were thrown; then father and son started wrestling.

Mary tried to leave. But David quickly grabbed her, smacked her face, and kicked her repeatedly in the belly. She was left cowering in pain.

The brawl continued until Mary escaped with Allan's help. But she knew it wasn't over, that she would have to return home. And she did. One evening nine days later, Sugarman walked through the front door, drunk again. He instigated another heated argument, put his hands around Mary's neck, and choked her three times. She almost passed out. When Mary — whose name New Times has changed because she is an apparent victim of domestic violence — later demanded he sleep on the couch that night, he responded, "I don't want to live anymore."

The two incidents, which allegedly occurred in July 2016, were reported in a temporary restraining order Mary filed in Monmouth County, New Jersey, the following year. They were part of a series of purported abuse that left her with a black eye and bruises on her arms, shoulders, groin, and torso. In the same document, Mary reported that Sugarman had broken all the doorknobs in the house on prior occasions and had even bashed in the windshield of her car while she was sitting in it.

Though the court ultimately granted Mary a restraining order, it is unclear whether she pressed charges for domestic violence, and Sugarman was never convicted of a crime in the incident. Attempts to reach Mary were unsuccessful, while Sugarman's parents, Allan and Joyce, declined to comment.

Sugarman himself is in jail, charged with failing to pay more than $300,000 in child support to his estranged wife, Shelly Berkovich. New Times unsuccessfully attempted to speak with him at a court hearing in Manhattan. After New Times sent him a letter detailing the attack and other charges leveled against him, Sugarman called back but declined to comment on the record.

"People are trying to make it look like [Sugarman] is a typical deadbeat dad who doesn't want to pay child support, but this man has a heart of gold," says Lynn Cohen, a 40-year-old self-employed publicist who says she has worked with Sugarman for more than 15 years. "He's the kind of guy who'd give his last dollar or the shirt off his back to someone in need. It's just heartbreaking that his two young children now have to miss out on having a father figure."

A vice president of at least two banks in Miami and a financial adviser for three others in New York, the now-41-year-old Sugarman has lived at two of South Florida's most exclusive addresses, the Icon Brickell and a $1 million house on Miami Beach's Pine Tree Drive. He's flaunted a fleet of at least 13 sports cars and drawn national attention for high-flying stunts, such as trying to buy Manhattan's Plaza hotel and announcing a run — which he didn't follow through with — for Congress in New Jersey. He's even appeared several times on CNN to push for the release of an American imprisoned in North Korea.

But court records and interviews with 11 people who say they have done business with Sugarman draw a very different picture. He has been sued more than 15 times in Miami-Dade County alone; among the lawsuits is a claim by a former employer that he stole clients and shared trade secrets with another firm. He has also been accused of fraud and charged with other financial crimes, including identity theft and larceny. He's been thrown out of at least three stylish residences, either due to evictions or foreclosures, and listed more than a dozen creditors, including former tennis star Jennifer Capriati, in a 2013 bankruptcy petition. He has had three domestic abuse restraining orders filed against him by two girlfriends, including Mary, as well as his wife, from whom he is separated. And in 2017, he pleaded guilty to a Class E felony for criminal possession of an unlicensed gun.

Last year, Miami attorney Jason Giller, whose firm represents Sugarman's separated spouse in a divorce proceeding, won a $10 million judgment against Sugarman for libel and abuse of the legal process, among other charges. "There is no greater example of a bully than Mr. Sugarman," Giller says. "[He] spares no mercy... yet boasts of the works he has done for humanity."

David Sugarman was born in 1976 in New York City's Mount Sinai Hospital and raised in a house adorned with black-and-white photos of celebrities.

The year after David's birth, his parents, Joyce and Allan, started a company that organized soap opera festivals where fans could meet the casts of The Young and the Restless and Days of Our Lives, among others. His mom was a former gossip columnist for Daytime TV, a monthly fan magazine. His dad was a graduate of Columbia University with a master's degree in special education and teaching, according to his LinkedIn profile.

The two soon became known for traveling festivals, which within a few years after startup were attracting crowds of 1,000 to 1,500 and grossing $350,000 a year (about $878,650 when adjusted for inflation). One show reportedly drew as many as 18,000 attendees at a mall in Edmonton, Alberta.

Despite the glamour, Joyce Becker insists everyone in her family has always been humble, charitable, and kind — including her son. "We lived in the biggest house on the block, but [David's] favorite toy was a corrugated box that he pretended was his house," she says.

David even donated his favorite toys and clothes to Ethiopian Jewish refugee children when the family visited Israel, she says proudly. He trained high-school teachers at Rutgers Preparatory School in CPR after Allan suffered a heart attack, and he saved the life of a 17-year-old girl knocked unconscious in a car crash — then waited three days in the hospital until she awoke.

"From the United States to Israel, my son did a lot of stuff that has gone unheralded," Becker says tenderly. "That's just who he is."

After high school, David attended two years of college at Lynn University in Boca Raton, followed by two years at Pace University in Manhattan, his mother says. In 1998, he began working at a stock brokerage, CIBC World Markets, according to federal records.

Over the next 13 years, he filtered through seven investment banks across New York City and Miami, rarely working more than two years at any one.

In mid-March 2005, David Sugarman had moved to his fifth firm, Morgan Stanley, where he worked as a financial adviser at an office on Brickell Avenue. Eighteen months later, he resigned to become vice president of a competing firm, Deutsche Bank Securities, in Miami Beach.

Just a week into the new job, he was sued by Morgan Stanley for allegedly violating nondisclosure clauses of his contract by "conspiring with his new employer, in all likelihood for significant financial incentive, to wrongfully solicit and divert Morgan Stanley customers to his new employer," according to court records. The case was ultimately settled for an undisclosed amount. Neither firm responded to New Times' requests for comment.

Two years later, Deutsche Bank fired him over undisclosed violations of company policy and "failure to adhere to a written warning concerning his performance," according to court records. Nine months after that, Sugarman sued, claiming religious harassment. In his initial complaint, Sugarman alleged his supervisors had made anti-Semitic comments about him, including referring to him as "you people." The court ultimately determined the teasing did not constitute a "religiously hostile work environment" and dismissed the case.

Despite the litigation, Sugarman promoted himself in social media videos and radio appearances as a successful businessman, often touting himself as a former vice president of Morgan Stanley, Deutsche Bank, and Merrill Lynch, where he later worked from 2009 to 2011.

He even apparently inflated his level of experience when speaking to radio hosts of ThisIs50, an entertainment station sponsored by rapper 50 Cent, in 2015. "I'm a Wall Street guy, so I spent 14 years on Wall Street [as] vice president of seven banks," he said. "That's where I come from... I'm a numbers guy."

In October 2010, he founded a sports agency, SugarTime Inc., on Ocean Drive and shortly thereafter left investment banking to pursue sports management full-time. That venture associated him with high-profile figures such as Michael Grieco, the now-disgraced former Miami Beach commissioner, who spoke about the company in a 2013 promotional video that identified him as "legal counsel." Grieco praised Sugarman and his business model for young athletes. "Ever since Jerry Maguire came out, everyone wanted to get involved [in sports management]," said Grieco, "[but] we want people to be wealthy for life as opposed to just rich for a few years."

Nearly five years later, Grieco, who is serving a year of probation for violating campaign laws, denies ever having worked with Sugarman. "I do not recall doing any formal legal work for [Sugarman]," Grieco wrote in an email. "He did refer me a criminal defense client once or twice, [and] I believe Mr. Sugarman listed me as his registered agent."

In December 2012, Sugarman partnered with Ronnie Chalmers, father of former Miami Heat point guard Mario Chalmers. Less than a year later, the two had a falling-out when Sugarman sued the elder Chalmers in Miami-Dade County Circuit Court for stealing confidential property in order to poach clients. The court ultimately dismissed the case for lack of prosecution. Chalmers could not be reached for comment.

Sugarman also worked with retired New Jersey Nets point guard Kenny Anderson, who in 2005 filed for bankruptcy despite having earned an estimated $63 million during his 14-year NBA career. Anderson, who once told Forbes his financial problems were due to two failed marriages and seven biological children, says he and Sugarman became fast friends and business colleagues. "[David is] a loyal, upfront guy," Anderson, now 47 years old, tells New Times. "He's worked with people in the business world, the basketball world, and the entertainment world. I really respect him."

While speaking with ThisIs50 radio hosts in 2015, Sugarman claimed the goal of his sports agency was to support young black athletes by managing their expenses. "You can change their lives for them, their mom, their dad, their grandparents, and their kids," he said.

In the 2013 promotional video, David claimed to represent 66 big-time NBA and NFL athletes with contracts reaching over $450 million "plus or minus a couple bucks."

"You ever see A Beautiful Mind?" he asked the camera. "I have a beautiful mind when it comes to business and sports. I see numbers fucking everywhere. That's why I come to work. I have $10 million days; then [I] can take the rest of the day off."

Cohen, his publicist, says he often took his NBA clients to public basketball courts to interact with inner-city youth and treated children from the Boys & Girls Club to Miami Heat games. "The kids were so excited," she says, "and they could high-five the players. It was unbelievable."

However, Real GM, a licensing business that tracks agents' clients, lists only four lesser-known European point guards under Sugarman's name. One of them, Greg Gantt of C.B. Valladolid in Spain, says, "He was very instrumental in landing me a position in the NBA D-League with the Spurs and helping me get a jump-start to my career." A.J. Walton of BK Iskra Svit in Slovakia isn't quite as laudatory. "I didn't feel like his whole heart was focused on being a basketball agent, so we parted ways."

David Sugarman (left) frequently posted photos on his social media accounts from TV studio sets and with sports celebrities such as Jae Crowder and Mark Cuban.
David Sugarman (left) frequently posted photos on his social media accounts from TV studio sets and with sports celebrities such as Jae Crowder and Mark Cuban.
Photos via Facebook

Dressed in a navy pinstripe suit with a baby-blue pocket square, Sugarman sat with his hands clasped across from CNN news anchor Don Lemon February 8, 2014. While the hashtag #BringBaeBack flashed on the screen behind them, Sugarman explained he needed a way "to get the world and the American people behind us."

Nearly two years earlier, Kenneth Bae, a 45-year-old Korean-American Evangelical Christian missionary, had been arrested in North Korea and convicted of plotting to overthrow the government. After Bae was transferred to a labor camp, Sugarman appeared on CNN to launch a social media campaign urging North Korean leader Kim Jong-un to release Bae.

Just three days before his appearance, Sugarman told Lemon, an online petition on Bae's behalf had collected fewer than 150,000 signatures. "It was of concern to me," Sugarman said. "More people are voting on American Idol versus voting or voicing their support for Kenneth Bae."

"I am so thankful for [David] and his team for reaching out to us and offering their support," Bae's sister, Terri Chung, said minutes later. "As a family, we don't have the resources to launch this kind of social media campaign, and we appreciate his advocacy."

Soon after that appearance, Bae, suffering from diabetes, an enlarged heart, gallstones, back pain, and massive weight loss, was freed.

On social media, Sugarman proclaimed his contributions to Bae's release one of his many achievements as a public figure. Over the next few years, he continued to dabble in ventures outside sports management, including politics and real estate. But then Sugarman filed for bankruptcy, lost his agent's license in Florida, and was even accused of failing to pay minimum wage to a member of his household staff.

None of that seemed to affect his lavish lifestyle. In 2010, while working at Merrill Lynch, Sugarman — then divorcing his wife of five years, Monica Vega — met Shelly Berkovich, a real-estate agent who had just moved from Toronto, for lunch at Joe's Stone Crab in South Beach. Charmed by Sugarman's striking blue eyes, New York charm, and philanthropic spirit, she married him nine months later in Key West and moved into his million-dollar house on Pine Tree Drive in Miami Beach. Soon the two had a daughter.

In the meantime, Sugarman continued splurging on designer clothes, Rolex Yacht-Master watches, and luxury cars, including Audis, Land Rovers, an Aston Martin, a Ferrari, and a Bentley, according to records from the Florida Department of Highway Safety and Motor Vehicles. There was even a gray Porsche, from which he pried the letters "P-O-R-S-C-H-E" off the trunk lid and replaced them with "S-U-G-A-R."

Then, in 2013, Jennifer Capriati, the tennis player who won three Grand Slam tournaments and a gold medal at the 1992 Summer Olympics in Barcelona, gave Sugarman $480,000 to invest. Within weeks of the transaction, Sugarman filed for bankruptcy protection, reporting $47,203 in assets and $1.3 million in liabilities, with Capriati listed as his biggest creditor. Just prior to his bankruptcy filing, on Christmas Day 2013, authorities repossessed his 2010 Range Rover, valued at $46,500. They had already foreclosed on a Collins Avenue condo, according to bankruptcy records.

However, after several creditors, including Capriati and the U.S. Trustee, contested Sugarman's petition for bankruptcy protection, the court found Sugarman was not entitled to relief and dismissed his case, barring him from further filings. Eventually, he agreed to pay the tennis star $510,701 over time.

Shortly thereafter, in 2014, NBA player Kenny Anderson, David's longtime friend, became embroiled in a national political scandal after visiting North Korea with athlete/celebrity Dennis Rodman. When a video of the pair and several others singing "Happy Birthday" to North Korea's Kim Jong-un surfaced, Anderson apologized to Piers Morgan on CNN for his role in the incident. Sugarman was at his side.

Soon, Sugarman began his campaign for the release of the missionary, Bae. In early February that year, he made a personal appeal for Bae's freedom to Kim Jong-un, again on CNN: "Human to human, I'm asking you to release Kenneth Bae... If the North Korea government actually needs somebody in North Korea, take David Sugarman. Allow me to go there. I'm younger. I'm healthier."

Seven months later, he teamed up with Fugees founder Pras Michel and two other businessmen to submit a $2.2 billion bid for Manhattan's Plaza and Dream Downtown, as well as London's Grosvenor House. Though the deal soon fell through, Sugarman again made national news when he was quoted by USA Today: "I'm not driven by money," he said. "I've had millions of dollars and not had millions of dollars... my drive every day is to really make a difference."

More headlines came in January 2015 when his 19-month-old daughter's nanny, who also maintained his condo in Manhattan and his estate in Marlboro, sued him for paying less than minimum wage. "It's inconceivable to me that a public figure like Mr. Sugarman would be involved in such a massive transaction as trying to buy the Plaza but won't pay his own domestic worker a legal wage," the nanny's lawyer, Jonathan Silver, told the New York Post.

Sugarman's response to the Post: "It really feels like a shakedown attempt."

Sugarman pivoted from rubbing shoulders with celebrities like Jamie Foxx (left) to projects such as meeting with ambassadors to discuss the release of an American imprisoned in North Korea.
Sugarman pivoted from rubbing shoulders with celebrities like Jamie Foxx (left) to projects such as meeting with ambassadors to discuss the release of an American imprisoned in North Korea.
Photos via Facebook

Then things grew worse for Sugarman. On October 21, 2015, he and his then-wife Berkovich argued over money being moved out of their joint account, according to state records. As Sugarman became increasingly angry, he began kicking things around, so Berkovich called 911. Once police arrived, they asked if there were any firearms in the house, and Berkovich told them her husband had a pistol in a cabinet and ammunition in a lock box. Noticing the pistol was licensed in Florida but not New York, the officers took Sugarman into custody and helped the wife file a restraining order against him. (Berkovich declined to comment for this story.)

Upon his release, the couple separated. A judge then required Sugarman to pay more than $15,000 per month in child support based on his earnings. He later pleaded guilty to a felony for having the gun and was sentenced to 30 days in jail and three years of probation, which he later transferred to Florida.

The following month, Sugarman met Mary, who would become the mother of his third child. Their romantic relationship lasted for nine months, including a vacation in the Bahamas, before Sugarman allegedly attacked her at their New Jersey estate, which resulted in another restraining order.

There is no indication in legal documents about when or if the two broke up, but the next year, Sugarman was issued a third restraining order for allegedly abusing another girlfriend in a $4,000-per-month apartment at the three-tower luxury condo Icon Brickell in Miami's financial district. According to court records, he hit the 22-year-old "several times." She did not respond to New Times' requests for comment, and it is unclear whether she pressed charges against him.

Two months after that incident, Sugarman announced a run for Congress in New Jersey. "I realized that I have a natural and unlimited concern for the rights of others," he wrote in a news release published online. "It's important for those of us who can speak out to do so and serve as a voice for those who have been silenced." But Sugarman's announcement went uncovered by media and, ultimately, unrecognized in the election. There is no record of a campaign account or candidacy in federal records.

The last line of the news release, though, mentions his business, SugarTime Inc., one of at least 18 corporations listed under his name in Florida. And he continued to solicit investors. Among his clients was Lisa Chmela, a glitzy, chestnut-haired 63-year-old Audi dealership manager from Sunny Isles Beach.

In January 2017, she now contends, she invested $25,000 in one of his companies, Basketball & Beyond. Chmela says that the money was to be used to support young, recently signed players until their "NBA contracts started paying out" and that Sugarman assured her it would be a lucrative deal. But within months of the check being cashed, she says, Sugarman stopped returning her calls and blocked her from his Facebook page. Weeks before she was due for an expensive and painful spinal surgery, Chmela was left thousands of dollars in the hole.

"I trusted David not to hurt me, but he did," Chmela says shakily. "David thinks that because he's 'Sugar,' nothing can touch him."

Later that year, in April, Giller, a University of Florida-educated Miami attorney, filed suit against Sugarman in Miami-Dade for fraud and breach of an oral agreement, among other charges. Four months later, the court found Sugarman guilty of contempt and issued a warrant for his arrest.

In May, Sugarman sued Giller, seeking relief of $2.5 million for libel and slander. In a pro se claim filed June 3, 2017, Sugarman wrote, "Jason Giller continues to portray me as dead beat dad [sic], who abuses drugs. The court will find proper due diligence I have done great work for humanity and Jason Giller just continues to bully and harass me."

Giller immediately issued a counterclaim, accusing Sugarman of libel, tortious interference, abuse of process, and malicious prosecution. On August 29, the judge awarded Giller a $10 million judgment and an injunction prohibiting Sugarman from filing another suit against him. The court noted that Sugarman had waived any defense by "failing to appear at the duly noticed and well-briefed Final Hearing and total lack of participation in [the] proceedings."

On June 2, Sugarman was evicted from the Icon Brickell condo. In August, he was also booted from South Beach's four-star Mondrian South Beach off Biscayne Bay, where he had lived for at least two months, spending upward of $10,000 a month. Receipts show he splurged on pricey table service and expensive Grey Goose cocktails.

This past November 9, he was arrested in New York City for defaulting on 24 months of consecutively missed child support payments to Berkovich — a debt amounting to $302,500. Just a few days earlier, Kasi Santarelli, who says she's Sugarman's best friend, set up a GoFundMe campaign, titled "Sugarman to See His Children." "No one is thinking about David or the children," Santarelli says. "This whole situation is over money, which is really sad, because it's not Jay-Z or Beyoncé getting divorced. It's a normal couple."

Thus far, the account has raised $7,321 from 55 people, including his first wife, Monica Vega, and Bae's sister, Terri Chung.

But "not a penny of that has gone to paying off any of his child support," Giller says.

Wrists cuffed behind his back, Sugarman slumps on a hallway bench in the Manhattan Civil Courthouse. Dressed in a white ski cap, baggy off-white sweatpants, and red New Balance sneakers, he looks up at a group of deputies and offers to buy them beers after his hearing. Apparently certain he'll be released, he explains to them, "I'm a good boy," and smiles.

At 10:25 a.m. December 18, 2017, a bailiff calls him into the courtroom. Sugarman trudges in, takes off his hat, and stands beside David Fish, a burly, bushy-browed lawyer from Garden City. After the two are sworn in, the judge asks if there have been any updates since Sugarman last appeared in court ten days earlier.

Fish says Sugarman has been trying to recover old sports memorabilia to liquidate for child support. Sugarman explains that when he left his home with Berkovich two years ago, he wasn't allowed to take these items and has since been unable to locate them.

An attorney for Berkovich, Charles Gayner, responds, "We don't care if Sugarman has the Golden [Jubilee] Diamond. At the end of the day, he's created a black hole for [Berkovich]. She's living off a government health program and the good graces of her family, while he spent $15,000 a month at the Mondrian."

Filled with rage, Sugarman begins screaming — "She's lying! She's lying!" — as his eyes grow bloodshot and watery.

But the judge just listens impassively and then pounds his gavel to end the hearing. Two New York City sheriff's deputies approach Sugarman and escort him out of the courtroom.

Sugarman has since paid $5,000, Gayner says, but remains in jail. He will be released January 22 to prepare for his upcoming trial for child custody and child support, beginning January 25.

"My son has helped so many people throughout his career," his mother says, her voice cracking. "My David was an incredibly charitable person, and he will be again."

Joseph Fanelli contributed reporting to this story.

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