Lil Baby Questions Jack Doherty’s Security Choices After $300K Theft

When you become a highly successful influencer, musician, or TV star, it’s only a matter of time before you cross paths with others in the same circles. YouTuber Jack Doherty and rapper Lil Baby were two such names spotted together in early May 2025, just days after Jack was robbed of $300,000 worth of jewelry on Rodeo Drive. The two also have some history — Lil Baby performed at Jack’s 21st birthday celebration.

The encounter was casual — Jack stood in the street while Lil Baby walked on the sidewalk. After recognizing the rapper, Jack made his way over to say hello, though their interaction lasted only a few seconds. During the brief exchange, a comment about Jack's security was made. Here’s a rundown of Jack and Lil Baby’s encounter, plus the details of the robbery that left Jack out $300,000 in jewelry.

When Jack Doherty and Lil Baby crossed paths in early May 2025, the encounter was brief but notable. In a short video clip, Lil Baby can be heard asking, "Y’all still got the same security?" before casually walking away. Jack’s friend later added that Lil Baby also mentioned he had some chains for him, though it’s unclear if he actually meant it or was just being sarcastic.

So why is this moment getting attention? Because just days earlier, on April 26, Jack had been robbed of $300,000 worth of diamond chains in broad daylight on Rodeo Drive. In a now-viral Instagram clip, a disheveled Jack approached the camera with his T-shirt collar torn, shouting that he had just been robbed, on Rodeo, of all places.

Lil Baby’s comment about security came after noticing Jack was still with the same guard who was present during the robbery. In a video recorded shortly after the incident, Jack is seen yelling at the guard for answers.

The guard explained the robbers had a gun, but Jack quickly shot back, "Where’s yours?" — a fair question, considering security is meant to prevent things like that from happening. So, it seems Lil Baby’s remark was less about teasing and more about questioning why Jack stuck with someone who couldn’t do the job.

While it's fair for people to question Jack's security, it's also worth asking why he was walking around with over $300,000 in jewelry and relying on just one guard to protect him from multiple armed men. In a TikTok shared on May 6, Jack explained that a car "skirts up and four guys hop out." Within seconds, they were running at him with their hands around his chain.

Jack said his guard, Dave, tried to grab and throw the guys off, but since they were all armed, it was an unfair fight, and the robbers obviously won. In a follow-up TikTok, Jack sarcastically asked Dave if he was in on it, to which Dave replied "yes," before the two ran off camera jokingly. Despite the humor, many people still feel something is off about the situation.

Jack also questioned whether the girl he was with had any role in the setup, especially since he had only met her two weeks earlier, and admitted to going through her phone afterward. So, for now, it seems Jack is keeping Dave on the payroll, but if he plans to keep flaunting valuables, he might want to consider beefing up his security team.