DMX wasn’t just a rapper—he was a movement. His raw energy, unmistakable bark, and street-hardened lyrics made him one of the most iconic voices in hip-hop. But behind the multi-platinum records, sold-out tours, and Ruff Ryders anthems, DMX was sitting on a chance to become a billionaire. And he fumbled the bag.
One of the biggest financial missteps in DMX’s career was turning down an opportunity to invest in Brooklyn’s Barclays Center alongside Jay-Z. Imagine X, the same man who took over New York’s streets with “Get at Me Dog” and “Ruff Ryders’ Anthem,” having a stake in one of the most valuable arenas in the world. Instead, he passed, reportedly uninterested in business ventures at the time. Meanwhile, Jay-Z leveraged his share into millions, proving that hip-hop moguls weren’t just running rap—they were running the boardroom, too.
If DMX had said yes, his financial future could have looked very different. But that was just one of many missed chances.
DMX was a rap titan—selling over 70 million records worldwide, dropping five consecutive No. 1 albums, and headlining massive tours. He was on top of the world. But despite his monumental success, his money management was a disaster. From the early 2000s, financial problems started creeping up—mismanaged funds, unpaid taxes, and failed business ventures piled up until his empire crumbled.
By the time he filed for bankruptcy multiple times, X was drowning in millions of dollars in debt, battling lawsuits, and facing jail time over unpaid child support and tax evasion. The same industry that once hailed him as hip-hop’s hardest working artist now watched as he struggled to stay afloat.
Turning down the Barclays deal was just the tip of the iceberg. DMX’s financial mismanagement stretched far beyond one missed investment. He had multiple bankruptcies, lost major endorsement deals due to legal troubles, and faced IRS problems that kept him from stacking real wealth. Unlike Jay-Z, Diddy, or Dr. Dre—who turned their rap fame into billion-dollar businesses—DMX never secured the long-term financial stability that his success should have guaranteed.
Even when opportunities knocked, his personal demons—drug addiction, reckless spending, and legal troubles—kept him from capitalizing on them.
Through all the ups and downs, one person stood by his side—Tashera Simmons. The two had a bond dating back to childhood, eventually getting married in 1999. She loved DMX beyond the fame, the money, and the chaos. But their relationship was anything but smooth. Addiction, infidelity, and legal issues tore them apart.
Tashera gave everything to their marriage, raising their four children while DMX battled his demons. But by 2012, she had enough. After appearing together on VH1’s Couples Therapy, she made the painful decision to walk away.
“I sacrificed so much of myself,”
she said. And still, she remained one of his biggest supporters.
DMX wasn’t just a husband—he was a father to 15 children. While he loved them deeply, the financial responsibility of supporting such a large family only added to his struggles. His children, especially the four he had with Tashera—Xavier, Tacoma, Sean, and Praise Mary Ella—were left to carry his name, his legacy, and the lessons he left behind.
Despite his financial troubles, DMX’s impact on hip-hop is untouchable. His music continues to inspire, his spirit lives on through his kids, and his story serves as both a warning and a testament to the unforgiving nature of fame and fortune.
What if DMX had made different choices? What if he had taken the Barclays Center deal? What if he had structured his career like Jay-Z, 50 Cent, or Dr. Dre? Could he have been hip-hop’s next billionaire? We’ll never know.
But if there’s one thing today’s artists can learn from DMX’s story, it’s this: talent alone isn’t enough. The game will eat you alive if you don’t play it right. Money needs management. Success needs strategy. And legacies need more than just legendary music.
DMX may not have left behind billions, but he left behind something just as valuable—a raw, unfiltered blueprint of what it means to be real, even in the face of downfall. And for that, he remains one of hip-hop’s greatest of all time.
Rest in power, Dark Man X.
