Luke, not the Brightest Star in the Galaxy

Amazingly the Rebellion Alliance won with this guy.  Though in Luke's defense his plan worked.

3) His Insanely Stupid Plan To Rescue Han Solo from Jabba The Hutt

Let us imagine that Luke Skywalker is trying to tell you his plan to rescue Han Solo from Jabba the Hutt.

Luke: "Okay so, first we get Lando Calrissian posing as a guard inside Jabba's Palace."

You: "How do we do that?"

Luke: "We just get him a costume and he--just walks in."

You: "Um, okay, say it's that easy. So then Lando gets Han out of the carbonite and we pick them up and get away?"

Luke: "No. What happens next is that I put my lightsaber in a hidden compartment in R2-D2 and send R2-D2 and C3PO to Jabba the Hutt as gifts."

You: "Wait, why-"

Luke: "Just listen. Next we have Leia pose as a bounty hunter arriving at Jabba's palace with Chewbacca captured. She's going to hand over Chewbacca to Jabba."

You: "Wait, why? Wouldn't that mean we would now have to rescue Han Solo, Chewbacca, R2-D2 and C3PO? That just makes it more difficult, right?"

Luke: "Just go with me here. Next, Leia is going to sneak around at night and get Han Solo out of the carbonite, but get captured."

You: "What? Why would we get everyone captured like that?"

Luke: "Now I'll show up, use my Force powers to get in to Jabba's fortress, get past the guards to an audience before Jabba and then use my Jedi mind trick to get Jabba to release everyone. If that doesn't work, then I'll get captured."

You: "Okay, if you can just use your Force powers to get in to the palace and all the way to Jabba, then let's just have you go in right now and get Han out."

Luke: "No, that's stupid. I'm going to get myself captured. Because then you see, we'll be taken to the sarlacc pit and then, when we're on the skiff, I'll get sent out first and then R2-D2 will manage to get to the top of Jabba's sail barge and shoot out my lightsaber, and then with Lando's help, we'll just--rescue everyone and then everything will be fine!"

You: "That is the stupidest plan I've ever heard of."

Luke:"I've thought of everything."

You: "Clearly you didn't."