Jay-Z seems to have landed himself in hot water, with many questioning his relationship with rapper Sean “Diddy” Combs. On October 28, fellow musician Freddy P discussed Combs’ scandal with YouTube channel The Art of Dialogue and wondered why Jay-Z had not publicly supported Puff Daddy despite the duo boasting about their friendship in the past.

For those uninitiated, Jay-Z and Diddy’s relationship dates back decades, with the two collaborating on multiple business ventures, including the music labels Bad Boy Records and Roc-A-Fella Records. As the duo built their own empires, they were spotted together at multiple award shows and parties.

In 2010, the duo also headlined a concert series together to praise each other’s successes and celebrate their friendship. Speaking about their relationship and raising speculation over Jay-Z’s silence in the midst of Diddy’s legal troubles, Freddy P said in his interview:

“Jay-Z, your son going through some financial issues right now. If Jay-Z supposed to be his uncle, he’s supposed to come through, right? Cut a check. Hold you off to the old boy, get right. These n***as ain’t going to come for you, Puff. They’ve been waiting because you didn’t deserve what you got.”

Freddy P went on to say that celebrities who were supposed to be Diddy’s friends “weren’t speaking up” because they were scared of what they were going to lose, and were going to look like they were affiliated with the rapper’s alleged activities.

Exploring Jay-Z and Diddy’s relationship as Freddy P questions the former not supporting the rapper amid legal tribulations

Diddy and Jay-Z became friends as the former founded Bad Boy Records and the latter found success with his first studio album, Reasonable Doubt under his own label. As Jay-Z created his next album In My Lifetime Vol. 1 alongside Diddy, the duo mourned the loss of The Notorious B.I.G.

The album marked their first collaboration and was followed by Diddy’s No Way Out album, which included Jay-Z’s Young G’s feature. The two were considered to be friendly rivals and endlessly praised each other.

During the celebration of what would have been Biggie’s 50th 𝐛𝐢𝐫𝐭𝐡day, in May 2022 Twitter Spaces, Diddy praised Jay-Z for filling in for Biggie and 2Pac after their deaths left a “void” in the rap world.

“Bro, you filled them shoes though. You came in and we definitely give thanks. You definitely came, and I just know how much Big really looked up to Jay. They looked up to each other. That is crazy you had to step into the shoes of two people. That’s all it was was those two people. They had things on lock,” Combs said.

Meanwhile, Suge Knight also slammed Jay-Z for staying silent amid Combs’ legal battle. In a September interview with Chris Cuomo on NewsNation, Knight said:

“I look at it real plain and simple: [I] ain’t no whistleblower. The facts [are] there but, right now, I don’t care if it’s T.I., I don’t care if it’s Rick Ross, I don’t care if it’s Jay[-Z], I don’t care if it’s Snoop [Dogg], I don’t care if it’s [The] Game, I don’t care if it’s Drake, nobody is stepping up.”

50 Cent also poked fun at Jay-Z for not speaking up for Combs, who was charged with pr*stitution and racketeering conspiracy as well. After Combs’ house was raised by the FBI back in March, 50 Cent shared a photoshopped picture of Jay-Z on a milk carton and wrote online, “Anybody seen Jay LOL”

Although Jay-Z has not publicly addressed Combs’ scandal in any manner, the rap legend, alongside his wife, Beyoncé, issued a “legal ultimatum” against Piers Morgan after Jaguar Wright shared disparaging remarks about the duo on Morgan’s Uncensored YouTube show.

Wright referred to Combs and Jay-Z as “monsters.” Wright went on to allege that Jay and Bey were “nasty” and kept people against their will. Jordan Siev, one of Jay-Z’s lawyers, said in a statement to NBC News:

“Piers Morgan’s irresponsible broadcast filled with lies is so far over the line that a legal ultimatum was warranted. Nobody acting under the guise of journalism can elicit outrageous statements from exploitative situations in an effort to drive clicks, and not have to answer for that.”

As Piers Morgan seemingly received a legal notice, he went on to apologize to Jay-Z and Beyoncé. Meanwhile, Diddy remains behind bars as he awaits his May 5, 2025 trial date.