Woodrow is seen "collecting" money from the ATMs in Slot Ranch Casino. He agrees to return to the Fortune City Emergency Shelter with Chuck, only if Chuck will guard him from the zombies while he "collects" the rest of the ATM's money. Once in the Safe House, he will award Chuck $50,000, in an effort to prove that he is not so greedy.
Be very careful when escorting Woodrow, as he will not equip any weapons/food as he is holding the steel briefcase.
When Woodrow is running, 100 dollar bills will fall from his briefcase, you can tell when this happens when you hear a "pop" noise.
In Dead Rising 2: Off the Record he is found in the shamrock casino in silver strip so you must take care of the Hunters because they'll shoot at Woodrow leaving him near death or dead.