Could you hide $100K from the cops?

That's why I think they probably held some open audition that said, "Try out to go on a reality show..." and the contestants had no idea what they were getting into.

Under those circumstances, unless you're familiar with the city, it's a pretty daunting task.

 

Probably the same way a lot of accomplice interrogations work.
Split the two people up and look for similarities and inconsistencies in their stories. Check it against the evidence you have (surveillance photos, forensics, witnesses, etc.) and confront them where appropriate.

Person A: We went to a department store in the Podunk Mall...
Cop: Which one? JC Penney? Sears?
Person A: JC Penney.

(Cop goes into the other room)
Cop: So your buddy says you went to the Sears in the Shelbyville Mall and bought a shirt. We have you on a security camera (an outright lie, of course).
Person B: He said that? He's mistaken. We went to the JC Penney's in Podunk.

From something as simple as that, they can start nailing down a timeline, look for witnesses and camera footage, see if you were carrying the briefcase or not (which could tell them if it's in the area, if it was close to the deadline) and lots of other things. They don't have to be confrontational at all.

 

Do you have spending money?

I would have one person driving the car frantically all over the place and making calls the whole time. I would have the other person on foot, with the money.

I would probably go to a gas station or bus station and shove the $$$ I'm assuming it's in 10 $10K stacks in the back part of a toilet and take your chances that nobody checks there (why would they?).

 

That wouldn't work. The cops could trace the car to the hotel, find the cab driver and figure out where you went. Every interaction you have leaves a trail.
The GPS and cellphone are great helps to the cops here, but some good old-fashioned police work goes a long way too.

 

I'm pretty sure you've got to keep the money inside the briefcase.

 

They are now. The police read SportsJournalists.com

 

Not if person A is Hadley, the toughest screw ever to walk the halls of Shawshank. He'd throw them off the roof.

 

For the plan to work, Person B needs to be this guy:

 

That's what I would do. That, or have one of the guys tuck and roll out of the moving car at a random point with the briefcase.

 

If it has to stay in the briefcase, that's considerably more difficult.

Normally, I would say go to a public park and bury it, but I doubt that could be done effectively in an hour.

 

If real life were a John Woo film, everyone involved in the show would die and the contestant would be accused of stealing $100,000.