Ouch - no where near that bad but once I was working on a children's online game. The game was large (500MB or more), and this was still pretty early on in ADSL roll out - lot's of kids still had dial up. So we offered a CD with the game on for free.
After 800 of them arrived for me to start mailing out, they found a small issue with the game, which they patched - "don't worry the kids will just have to run the patch the first time they play" - I tested it, the patch was 800MB...
I worked at a game company in the 90s that shipped a strategy game with a bug where the AI would literally never attack the player. I think the cause was some last minute copy/paste while rushing to deliver the game to the publisher. It was discovered before the game hit the shelves, but the decision was made to ship it anyhow and release a patch, which had just become a somewhat reasonable practice with all those 33.6k modems out there.
I just managed the website - I wasn't involved in the game, but it didn't seem to be that well managed from my outside perspective.
I think part of the issue was there was not system to 'patch' - so the far larger download in theory allowed them to add smaller patches to the game in the future, but that didn't happen as far as I remember.
I don't think we even ended up opening all the levels of the game as the uptake wasn't that great.
After 800 of them arrived for me to start mailing out, they found a small issue with the game, which they patched - "don't worry the kids will just have to run the patch the first time they play" - I tested it, the patch was 800MB...
I didn't send any of the CDs out.