Screenwriter
Brad Pitt and producer Brad Grey decided to go with William Monahan to write the screenplay for The Departed. Well, it might be more accurate to say that they asked him to adapt the screenplay of Infernal Affairs, which was the name of the Hong Kong movie they were trying to remake.
Monahan had only had one of his screenplays produced before The Departed, but maybe Pitt detected something in the fact that Monahan was an Irish descendant who had been born and raised in Massachusetts. The decision would pay off, and Monahan would end up doing a good enough job to win the Oscar for Best Adapted Screenplay in 2007.
Apart from writing The Departed, William Monahan has written the screenplays for films such as Kingdom of Heaven (2005), Body of Lies (2008), and The Gambler (2014). These are pretty different movies in pretty different genres. Kingdom of Heaven is an action movie about medieval crusades, while The Gambler is a thriller about a mathematician who learns how to beat the odds at Vegas. So, yeah—Monahan has some range on him.
On top of his movie accomplishments, Monahan wrote a well-reviewed novel back in 2000 called Light House: A Trifle. It looks like this novel was one of the first things to get Monahan a lot of attention from Hollywood, since all his screenplay productions came at least five years after this novel. Warner Bros. actually bought the film rights for this novel before it was even published, so they must have seen some talent in the guy.
In case you're wondering, though, this movie was never produced, and Monahan eventually bought the movie rights back from Warner Bros. As far as we know, he's still holding on to them.