Kriti Mehrotra
With Paramount+’s ‘The Real Wolf of Wall Street’ delving into the offenses perpetuated by now-barred stockbroker Jordan Belfort, we get a true insight into the underworld of white-collar crimes. In fact, it incorporates archival records, exclusive interviews, and old footage to truly underscore the even darker reality of the tale narrated in Martin Scorsese’s ‘The Wolf of Wall Street.’ Amongst those to thus feature in this 3-part documentary series is Howard “Howie” Gelfand, a Partner at the pump-and-dump brokerage firm once operated by the aforementioned fraudster.
Howie Gelfand Understood the Value of Money Early in Life
Born in Flushing in Queens, New York, into an affectionate, kind, loving, and supportive Jewish family, Howard “Howie” Gelfand truly believes his childhood was nothing too cozy or “special.” The only thing of note he mentioned on the show is that’s where he gained a lot of weight at a young age and became “you know, a fat f***,” resulting in him being bullied in school by his peers. One example of such an incident was when he was cornered in the boys’ room and stabbed in the arm with a lead pencil by a girl for his lunch money, which he had wholly refused to give up.
According to Howie’s accounts, his protective mother freaked out the moment she heard what had transpired and decided to move the family into the suburbs, leading them to Long Island. “Little by little, I started to see how the other half lives,” he said on the show. “I was by far and away the poorest kid in a very wealthy neighborhood. So, I said to myself, I need to make money.” Therefore, when a friend called the University at Albany Business graduate in 1989 and offered him a job that could earn him hundreds of thousands of dollars per month, he quickly said yes.
Howie was admittedly just 22 years old when he joined Jordan Belfort’s boiler room brokerage called Stratton Oakmont, and he still remembers he was the baby among his 20 to 25 colleagues. As per his own accounts, they were all his inspiration owing to their luxury lifestyles, fancy cars, and opulent homes, gradually making him set a target of earning at least a million dollars per month. The perfect candidates to actually work the pump-and-dump stock sales were “young, dumb, broke, and hungry” youngsters, he claimed on the show, indicating it was a bill he fit at the time.
Howie Gelfand Engaged in Defraudation and Debauchery for Years
While Howie was well aware that the company’s cold-calling practices toward potential investors were aggressive, he initially had no idea the path he was on was not only wrong but also illegal. The first time he ever suspected something was amiss was on Christmas Eve 1990, the evening the admitted workaholic opened the largest account in Stratton Oakmont’s history until that point. According to his accounts, he closed a pretty big deal before walking into a Partner’s office and claiming, “I have a funny feeling that if that stock goes higher like I just told him, he’ll buy more.”
By the time Howie returned to his desk, that exact stock had gone up three-quarters of a point, making him wonder if he was that smart or if the Partner he’d just spoken to had done something. However, because the young man had his own goals in mind, he decided not to ask questions and immediately called back his investor, who purchased double the amount he’d already bought. Although he had recognized there was “some funky dunky going around,” his personal success led him to stand by the company, gradually climb the internal hierarchy, and ultimately end up as a Partner himself. In fact, he remained at Stratton Oakmont until it closed its operations in December 1996.
During these years, Howie admittedly also engaged in extensive use of recreational drugs alongside his colleagues, partners, and bosses, with the most common being methaqualone (Quaalude) and cocaine. He said on the show that he even attended countless lavish parties across the globe with the company, where there was no shortage of debauchery, sex workers, and substances. In fact, he claimed they all let loose at these parties in a manner worse than what is depicted in Martin Scorsese’s 2013 film, ‘The Wolf of Wall Street.’ So, he concedes he was completely addicted by the mid-1990s, only for the stress after the company closed to make him spiral deeper into his substance/Quaalude use.
Howie Gelfand Has Managed to Turn Over a New Leaf
When the National Association of Securities Dealers (NASD) expelled Stratto n Oakmont and put it out of business in 1996, Howie claimed he managed to walk away with a million dollars in cash. He thought he could stretch it for the rest of his life, but he soon realized his expenses were more than $30,000 per month due to his drug habit, fancy cars, luxury apartment, and familial responsibilities. The money thus quickly vanished, leaving him broke and homeless by the time he was sure the Federal Bureau of Investigation was looking into him for his alleged financial crimes. So, in the late 1990s, he decided to go to them himself, reveal everything he’d done while at Stratton Oakmont, and agree to wear a wire so as to help them really dismantle the white-collar underworld.
As a result of his actions, Howie claims he “avoided ever getting arrested, indicted, charged,” or convicted of any state and federal offense, but his entire world had already turned upside down. That’s because his lifestyle had gone from that of a prince to that of a homeless person, and he still admittedly has no idea how his dog managed to survive by his side all those years. Ultimately, it was his brother who helped him secure a spot in a sober house, where he managed to stick to the program, recognize the errors of his past, and turn over a new leaf for good. Therefore, today, he has been sober for over 2 decades despite still admittedly grappling with all the “damage he caused” for the investors while at Stratton. Howie stepped back into the workforce in the fall of 2009, joining SBLC Consultants as a Sales Director in October and serving there for a year before moving on to Friedman Law Associates.
He worked there as the Vice President of Client Relations from 2010 to 2012, and then he climbed the ladder to join FlexBorrow as a Partner from May 2013 to February 2015. He was subsequently a Partner at Fordham Capital LLC from January 2016 to July 2024 and the Principal CEO at The Resurgence Group from June 2016 to July 2024. During this period, he also became the Founder-CEO at Bespoke Air Group, a private jet-focused travel company that began operations in January 2017. Coming to Howie’s personal standing, he is currently based in Syosset, New York, where he is proud to be a father of 2. He is divorced, but he shares his pride and joy, now-adult Josh Genfeld and Bari Genfeld, with his ex-wife.
Read More: Nadine Macaluso: Where is Jordan Belfort’s Ex-Wife Now?
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