The success of Brooklyn Nine-Nine hinged on the various relationships between a group of tight-knit NYPD detectives. But as close as they were, there was still an enigma in their midst named Rosa Diaz. She took privacy to new levels, hiding as much of her life as she could from both her friends and family. As various parts of her backstory came to light, she actually became a more confusing and compelling character.
As a precinct, the 99 functioned like a mix between a team and a family. This is a crew that knew everything about the other members, which was an important part of trusting each other in the field. In the case of Hitchcock and Scully, that was taken to the extreme, as their teammates knew a lot more about them than they wanted to. Those two were like horrifying onions with endless layers of disgusting truths that they were all too happy to share.
Rosa, on the other hand, was far more secretive about her life. She and Jake actually went to the police academy together, so when the show starts they've known each other for many years. Yet Jake somehow knew next to nothing about her. They had a relationship built on mutual trust and innumerable shared experiences. And yet even he didn't know her on a meaningful level. To be frank, no one did.
This was definitively proven in Season 3, Episode 23. As part of a plan to get information from a crooked FBI agent, she let the gang into her apartment for the first time. Then Amy discovered that Rosa was leasing that apartment under an assumed name. After the mission was completed, Rosa moved out of her home and presumably abandoned her fake identity in the process.
It was a prime example of how closely she guarded her past. That didn't stop details from slipping out, though, many of which didn't add up. She was a ballerina. She spent three years in medical school. She went to business school. She has a pilot's license. At one point, she reputedly had problems with cocaine and guns, even ending up in juvie at one point. But it's hard to figure out how all of it fits together.
If Rosa spent time in juvie, and had problems with illegal substances, it's hard to imagine how she was able to get into the NYPD. In Season 6, Episode 3, Gina revealed that she stopped Jake from making a mistake in high school that would have prevented him from joining the NYPD later in life. Presumably, no one helped Rosa in this same way, so she shouldn't have been able to join. Particularly since what Rosa allegedly did was way worse than what Jake almost did.
There's also an issue with timing. No one knows exactly how old Rosa is, but she appears to be closing in on 40 by the end of the series. Assuming that's true, that's not a lot of time to have lived the extremely full life Rosa has. On top of the different career paths she's embarked on over the years, Rosa has also heavily implied that she has lived in multiple cities and countries around the world. But all of this can be explained.
Everything goes back to Amy finding out that Rosa's old apartment was leased under an assumed name. Rosa would go to virtually any length to protect her privacy, including making up a fake identity to lease an apartment. It wouldn't be a stretch for her to make up a few details about her past, as well. All of it could be true. Or none of it. That's the mystery of Rosa Diaz which will never be solved, nor should it.
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