Dave Free built TDE alongside CEO and founder Anthony "Top Dawg" Tiffith and his co-president Terrence "Punch" Henderson.
According to multiple sources who spoke to Rolling Stone, Free is no longer with the label and has been working on his own for several months, directing the career of rising rapper Baby Keem.
Representatives of Free and TDE refused to speak on the record about the split.
In addition to his executive duties, Free directed videos for TDE's artists.
In an interview early this year, Free admitted most of the stuff they did in the early days of TDE would no longer work.
"Oh man, the approach is totally different. I was actually telling a buddy of mine because he just thinks we just have all the cheat codes, we just hit a button and they could just be famous the next day," he said. "None of the tactics we used back in the day to break Kendrick, Ab-Soul, Jay Rock or Schoolboy would work now, none of 'em. It’s a whole new game. Blogs were very influential back then and I’d have to build a lot of relationships with blogs and now it’s just more about streaming. You have to have the relationships with the streaming sites and it can’t just be a fake relationship. It has to be a relationship of understanding. Back in the day, if a blog posted a bunch of stuff, it was no hurt no foul. For streaming, they centralize. They have to post what works for their system too, it’s kind of back to a radio format a little bit in a sense."