It's a bit like when a bunch of ninjas attack the hero, and the ninjas all go in one at a time and get flattened, rather than all attacking at once and overwhelming the hero by sheer force of numbers.
Ninjas always do this when faced against heroes. It's part of their secret ninja training.
GM: Luke, it's a day later. None of the others have returned from Jabba's palace.
Luke: They've been captured.
Han: You don't know that! We could all be...
Han: Okay, we're captured. Wow. I was a real trendsetter there.
Leia: I had to go in to rescue you.
Luke: We all should have gone in with the droids.
Chewbacca: And now I have "pretending to be a Wookiee-gram" on my resumé for no reason whatsoever.
C-3PO: Hey, apparently the plan relied on us getting captured. We did our part.
R2-D2: Given I had the Lost Orb, I didn't think I needed a plan. But I should have seen the rubber suits coming.
Luke: Going in one by one was awful.
GM: So what are you doing?
Luke: <sigh> Going in alone.