Oswald in the doorway: the blog of the Oswald Innocence Campaign, by Ralph Cinque

I hope I have convinced you that it could not have been a friend of Oswald's who picked him up. It could have been ostensibly a friend but not a real friend. In other words, it could have been a handler, but someone who was setting him up and betraying him.

But, even that doesn't work. That's because anyone working for the conspiracy would have been bent on framing Oswald for the Tippit murder. Tippit wasn't murdered until 1:15, and Oswald was in the theater by 1:07. That's right; Oswald was in the theater when Tippit was still living and breathing. Wouldn't it have been better for a conspirator driver to delay getting Oswald to the theater in order to support the timeline for him killing Tippit?  

So really, you can't have a friend picking up Oswald, and you can't have an enemy picking up Oswald either. You just can't have anybody picking him up.