Multibot
Todd's server did not (initially?) deal tournaments, but, if I remember correctly, some of us chose to create the tournament experience by starting at a table and raising the blinds as we played. There were many drawbacks to these (up to 23-players for Hold'em) tounaments.
On Halloween 1998, I wrote the core of "multibot", an IRC bot to deal multi-table tournaments. I did it on Halloweeen because I knew that the constant interruption from trick-or-treaters would preclude me from doing Macintosh emulation work that required serious concentration.
Although multibot's core was initially in C, I soon rewrote multibot in Objective-C, a language that I had to use to port Executor to NeXTSTEP. I wound up liking Objective-C and used multibot as a vehicle to help me learn it better.
I needed money
I had planned on making multibot open source, but I had a loan that I I needed to pay back.
They needed Poker Software
The Napolitanos
So, I wound up selling multibot to the Napolitanos where it became the server for Poker School Online.
Multibot needed a graphical client and support
Mike Wing
My friend Mike Wing wrote the core of the Java client for multibot.
Gavin Scott
Gavin maintained and extended multibot at Poker School Online.