The Moment: Pro skater Terry Kennedy took issue with Lupe and his affinity for skateboarding (or, at least, his perceived affinity for skateboarding) on the Beef IV DVD in 2007.
The Reaction: They eventually patched things up, according to TK, but the controversy surrounding this incident was that at one time this was the only thing keeping Lupe's name out there in the news.
Did It Help or Hurt His Career? HURT! Though Lupe didn't cooperate with the producers of Beef IV and didn't appear on the DVD, his name got dragged into a nonsensical beef that made him a part of something petty. And that's never a good look.