Will Smith Admits Regret in Handling Jada Pinkett Smith’s Relationship With 2Pac: ‘I Was Deeply Insecure...Wasn’t Man Enough to Handle That’

Illustration for article titled Will Smith Admits Regret in Handling Jada Pinkett Smith’s Relationship With 2Pac: ‘I Was Deeply Insecure...Wasn’t Man Enough to Handle That’
Photo: Frazer Harrison (Getty Images)

Just because Will Smith is one of the most successful human beings in the history of ever doesn’t mean he’s not susceptible to jealousy just like every other husband.


During a visit to the popular morning show The Breakfast Club, the Bad Boys for Life star admitted that the well-documented bond between his wife, Jada Pinkett Smith, and rap icon 2Pac, born Tupac Amaru Shakur, wasn’t exactly something he was ever comfortable with.

Host Charlamagne Tha God opened that bag of worms by asking the 51-year-old if he was ever jealous of the connection between the love of his life and 2Pac, and Will got right to it.

“Oh, fuck yeah,” he admitted. “Oh my god. And you know that was in the early days, too. That was a big regret for me because I could never open up to interact with Pac.”

He continued, “We had a little bit of a thing, right? Because they grew up together and they loved each other but they never had a sexual relationship. But then they had come into that age where now that was a possibility and Jada was with me, so Pac had a little thing on that. But she just loved him, he was the image of perfection. But she was with the Fresh Prince.”

Will went on to detail how that dynamic created some awkward moments between him and the “California Love” rapper despite Jada’s insistence that the two had much in common.

“We were in the room together a couple of times and I couldn’t speak to him. And he wasn’t gonna speak to me if I wasn’t gonna speak to him,” he added. “Jada would say all the time, ‘I’m telling you. Y’all are so similar. You’ll love him.’ And I just never…That was a huge regret of mine. That I couldn’t handle it. I was the soft rapper from Philly and he was Pac. [...] I was deeply, deeply insecure and I wasn’t man enough to handle that relationship.”


It’s unfortunate that Will and 2Pac weren’t able to set their differences aside prior to the Death Row Records signee’s death in 1996, but Jada has remained vigilant in protecting both 2Pac’s legacy and their friendship in the years since.

In 2017, she dismissed the biopic All Eyez on Me as “deeply hurtful” for how it portrayed their inseparable bond.


“Forgive me...my relationship to Pac is too precious to me for the scenes in All Eyez On Me to stand as truth,” she posted on Facebook. “The reimagining of my relationship to Pac has been deeply hurtful.”

Menace to supremacy. Founder of Extraordinary Ideas and co-host and producer of The Extraordinary Negroes podcast. Impatiently waiting for y'all to stop putting sugar in grits.


Tupac wasn’t no gangster and was as big a nerd as Will Smith; which is why she liked both of them.