Deadpool, Vol. 3 #13 (2009)

Wave of Mutilation, Part 1: Profiteerin' L.A.M.F.
Deadpool now has a lot of money. He decides to use it to get more money, starting by taking over a small island known as a rich man's resort, only to find that other pirates have arrived first. What are he and Bob, Agent of Hydra, supposed to do now?
Release Date: 2009