Gay nightlife in 1969 was something quite different from what it is today for a couple of reasons. One of those reasons was that they tended to be owned by organized crime families, rather than by actual queer people. While this didn’t usually work out in the favor of the customers, it was just fine with Tammy Novak.
Tammy Novak was 18 years old in 1969, and was living — as far as I can tell — fully transitioned into life as a woman. Typically, a transvestite (the popular word of the time) would only be allowed into a place like Stonewall Inn if they were wearing at least four articles of “gender appropriate” clothing — the minimum allowed by law. The idea was that by making sure everyone was “gender appropriate” it would minimize police attention (and that worked out so well, clearly…)
But Novak had lived with Fat Tony of the Genovese crime family — the owners of Stonewall Inn — and so she was allowed to come and go as she pleased, no matter what she was wearing. She was also friendly with Chuck Shasheen, who ran the bar.
It was because of these connections that Tammy was in the bar when it was raided by the police on June 28, 1969 — and she immediately caught the attention of the police. There’s some (kind of unreliable) eyewitness testimonies that Tammy was on a lot of drugs that night, and seemed not to realize what was going on until the shouting outside of the bar snapped her out of it. She was almost in the police wagon (that drag queens were being loaded into) at this point, but turned and swung at the police — she made an escape attempt.
This — like so many other moments — was claimed by some to be the moment that sparked the riots, but with the shouting being a pretty key part of the story, my guess is this was happening just after or around the same time that Stormé Delarverie was being arrested. During the confusion that followed, Tammy made her escape. She took refuge in the apartment of drag performer Joe Tish.
There doesn’t appear to be any record of what happened to Tammy after the riots. This is partially because she wasn’t the only Tammy Novak in New York in 1969 — the other Tammy Novak was a performer at a place called 82 Club, and was not involved in the riots in any way, but it does make it more confusing when you’re trying to find out what happened to this Tammy Novak.