I can make a case for the Flying Pigs. Not AirWarrior old, but started with Hitech Creations certainly.
We used to be at
www.flyingpigs.com. I started playing Air Warrior on GEnie in 1991, and that's when I met DoK GonZo and many of the legends of the Air Warrior crowd such as Drex flying the A20. If you want to hit the way back machine, I can remember when Air Warrior had a new module, a film editor, coded by a young programmer turk named Dale 'Hitech' Addink. Oldest player I knew then, and this was 1991, was Ghost Rider, who was in his late 60s early 70s back then, and I believe actually served in WW2.
The Pigs started in Dale's first venture, Confirmed Kill. This predated Warbirds. It was for pre IP stack Windows, pre Win95 machines where you had to install a telnet client and telnet to the server once you established a SLIP/PPP link and then started the game and ran it that way.
Early members were Tigershark and Sean 'eagl' Long. The Pigs fought for the Gold color (never Red, and especially not purple, that was the Black Sheep color). Chris "CJ" Martin (callsign: smut) actually founded the squad via a mailing list. Chris is best known for being a producer on what is, arguably, the finest flight sim for the PC ever created, Jane's F-15 by EA. Up there with Falcon 4.0 and the follow on F-18 game.
I commissioned an artist by the name of Mary Lynn Skirvin to draw the FlyingPigs logo. I'm ashamed to say I can't find the logo at the moment, and the flyingpigs.com web site is no more. But it was so top notch that I had to send cease and desist letters to guys in Singapore who made coffee cups and t-shirts with the logo and sold them on the street. A USAF squadron approached the Pigs and the flying pigs logo is now the official logo of a real B2 bomber, the logo was etched on the plane itself, on a steel plate near the ladder.
I know weird little tidbits, like the blue doll under the desk in the old Warbirds tower with the pins sticking out of it is Dale's little message to a certain player from that era.
If I can find somebody who has the flyingpigs old logo, I will try and post it somewhere. Tigershark had it professionally inked and it was very popular for a time. Other Pigs of that era where Steve 'ichi' Dunbar and Bernie 'Worr' Worrell, Glen 'roamer' Becker and many others, including Marko 'mili' Milisevic and Vila.
-XX- - apologies for any inaccuracies in advance
Edit: I found the logo. If you want to strip it and add it to the time line, here it is:
http://web.archive.org/web/20030321104156/http://www.flyingpigs.com/