Brooklyn Nine-Nine: 10 TV Characters Who Would Make A Great Assistant To Captain Holt

2. Adrian Pimento

When hiring for a trusted position like the assistant to a police captain, you want a known quantity in the role. It should be someone who is familiar with the neighborhood, with the department and with the NYPD in general. A former detective might be an excellent choice, particularly if they're someone the captain already knows.

Adrian Pimento still might not be the best choice. Spending 12 years undercover with Jimmy "The Butcher" Figgis did a real number on him. He witnessed hundreds of horrifying acts, committing several to maintain his cover. He came out of his deep cover a crazy, paranoid lunatic.

That being said, Pimento might have been like that before he went in. The only people who knew him before he went undercover were Scully and Hitchcock. The only knowledge you can trust them with would be a list of the best hot dog vendors around New York. Don't laugh. That level of insight has proven useful.

While Adrian would not be a traditional assistant who was good at filing or answering the phone, he would be a highly effective gate keeper. The Commissioner would be hesitant to walk through that door with a shirtless, crazy eyed Pimento staring him or her down.