The worst days would have to be any number of dumpster fires that took place in the lost decade of the 1990's.
-The decade started off with the Grey Cup having to be papered in order to get even a half decent crowd out. The Stamps, Lions, Riders, Rough Riders, Ticats were all in major trouble of going under.
-The WLAF had established a franchise in Montreal and it was felt that the then new Skydome had outgrown the CFL and it was time for the NFL to come to town (with Montreal thinking the same with Olympic Stadium).
-The major superstar in the league wasn't paid in full and had to be shipped out to another team for largely financial considerations.
-The major star player coup from the NFL had to leave the league because the team that signed him couldn't pay any more.
-The league had a string of possibly the worst owners in Canadian and perhaps any sports history.
-League coffers were empty on a yearly basis. Rumors one of their member teams had to bail them out one year. (Their broadcast partner DID bail them out with a $$$ advance or the league would have went bankrupt.
-Faced with bankruptcy, the league is forced to expand to the US and subsequently grants franchises to whomever comes to them with cash.One team was added and a 2nd expansion team in was cancelled when financing did not materialize. Even worse one team is granted a franchise that doesn't even make it through their first press conference never mind actually ever seeing the field of play. Some of those owners later decide they don't want to pay the full expansion fee or accommodate a CFL regulation field, but the league is powerless to do anything about it. American experiment dies after the NFL returns to the best American CFL market.
The year after all American teams die, the Grey Cup is a financial disaster that again threatens to take down the whole league. And only the strongest franchise in the entire league is able to pull of a Grey Cup on short notice that allows the league to pocket some much needed money.
-Players are forced to take even further salary cuts in order to save the league. Sponsors jump ship in droves.
-One of the greatest teams to ever step on a CFL field is drawing Triple A baseball type crowds to their home games.
-The league gains back one market, only to see another fold with a whimper, and watches over a century of tradition flushed down the drain.
-One singular guy comes along and offers to buy the entire league.
-Rival (not really) league steps up with a financial loan to keep the league from going under.
-Grey Cup sellouts are a distant memory now. Even smaller venues (except one exception) fail to even come close to selling our the marquee game. Long term TV partner doesn't really feel like putting any effort into production and proposes to start airing games only after Labour Day (ya, cause their other programming is so great :roll: )
Then there was the Gliebermans, Forrest Gregg, Nick Miletti, Donald Crump, Jo Anne Polak, those ridiculous jerseys with the logo on the front, Horn Chen, holding training camp in local area high schools, having players sleep in livestock barns, practise roster guys sleeping on soiled used mattresses, players making more at their off season jobs than they do on the field, American announcers who know nothing about the game, parking lot practice field, center field logo at Ivor Wynne being harder than cement to fall on, drafting a dead guy, TV black outs, O' Christmas tree anthem etc etc etc.
Yup, the 90's were a banner decade for the CFL