Elon Musk recently took a shot at Jennifer Lopez after she told women not to vote for Trump, sarcastically asking, “How many people did she warn against Diddy?”
While Trump’s win seems to have killed off the celebrity political endorsement for good, it’s still a question worth returning to. From the looks of it, the answer is none.
A witness later claimed to have seen a female hand toss a weapon from the car, an observation that led some to suggest Lopez might have been more involved than initially believed.
Lopez’s relationship with Sean “Diddy” Combs, from 1999 to 2001, spanned one of the most turbulent chapters of his life. While the slippery showman was then at the height of his power, he also weathered explosive controversies — most notably a notorious 1999 nightclub shooting.
This sudden burst of violence cast a long shadow over everyone involved — Lopez included. More on that in a moment.
Coincidental connection?
The timing of Lopez and Diddy’s relationship coincided with her ambitious pivot from acting to pop stardom. A wise pivot, I might add — anyone who saw her stumping for Kamala Harris knows she’s better suited to lip-syncing than line reading.
Her debut album, “On the 6,” was in its early stages when she began dating Diddy, the head of Bad Boy Entertainment, a powerhouse label under Sony — the same company backing Lopez.
As her rise in the music world mirrored her time with Diddy, speculation mounted that their connection was more calculated than romantic, more strategic than sincere. Known for mentoring stars like Mary J. Blige and Usher, Diddy was key in shaping Lopez’s image as a credible singer. Lopez herself often called him a mentor, one who guided her through the creation of her first album.
Then came the night of December 27, 1999. Lopez and Diddy were at Manhattan hot spot Club New York when an altercation between Diddy’s crew and another group erupted into gunfire, injuring bystanders. Amid the chaos, Lopez stood beside Diddy, bearing witness to an incident that would dominate headlines for months.
In the aftermath, the police arrested Lopez, Diddy, and other members of their group after a gun was found in their vehicle during a high-speed attempt to flee the scene.
A witness later claimed to have seen a female hand toss a weapon from the car, an observation that led some to suggest Lopez might have been more involved than initially believed.
However, the exact nature of her role remained unclear. Despite her arrest, Lopez was eventually released without facing charges, while Diddy prepared for a lengthy legal battle.
Fall guy
During the trial, reports emerged that he had offered his chauffeur, Wardell Fenderson, money and even a diamond ring — a gift from Lopez — to take the blame for the gun found in the car. Although Fenderson initially complied, he later recanted.
Throughout the ordeal, Lopez kept a low profile, avoiding public comment on the shooting or her relationship with Diddy. Her silence, however, only fueled the flames.
Was she complicit in a cover-up, or was she strategically distancing herself to protect her rising career? Public appearances and interviews sidestepped the trial, focusing instead on her music and god-awful movies.
Meanwhile, Diddy’s defense, led by high-profile attorneys Johnnie Cochran and Benjamin Brafman, successfully painted him as uninvolved in the shooting, while Moses “Shyne” Barrow, a young rapper on Diddy’s Bad Boy label, bore the legal consequences.
Barrow’s defense admitted he fired a gun in self-defense, contrasting sharply with Diddy’s complete denial.
In the end, Diddy walked free, while Barrow took the fall, serving nine years in prison. Lopez’s choice to stand by Diddy until the trial’s end only intensified the intrigue. Yet their relationship, like her career today, quickly faded into obscurity.
But the ghosts of the past have a strange way of resurfacing.
Barrow — now a member of the House of Representatives in Belize — is making the rounds as the subject of a new documentary, which can’t help but put renewed scrutiny on that fateful night.
Jenny from the (cell) block?
As Diddy faces new federal charges of racketeering and other alleged crimes, the possibility of the nightclub shooting re-emerging in court looms. Lopez’s presence that night places her in the spotlight — as a potential witness or, conceivably, a participant.
Her testimony, or lack thereof, could be pivotal if investigators decide to revisit the incident as part of a broader investigation into Diddy’s criminal associations. But Lopez’s entanglement with Diddy runs far deeper than that single night.
The recent lawsuits lay out allegations stretching from the 1990s through 2022, a time when Lopez and Combs were America’s ultimate celebrity power couple.
A 37-year-old woman claims that Combs assaulted her when she was just 13 — with the help of an unnamed male and female celebrity — at an afterparty Combs hosted following the 2000 MTV Video Music Awards. The lawsuit doesn’t reveal the identities of Combs’ alleged accomplices, but Lopez was his date that night, taking home the award for Best Dance Video.
Jenny may be from the block, but she could soon find herself looking at a very different kind of block — concrete walls and cold steel.