Lot of highs and lows with this franchise. Purely from a 1 game view, off the top of my head, here's the list of heart breakers that come to mind:
1. 1984 Game 7 Division Finals against the heavily favored North Stars, Blues down 3 games to 2, shut the Stars out in Gm 6 and go on the road against the cocky North Stars and score a short handed goal from Wickenheiser to Reeds with about 4 minutes to play. The Blues were headed to play Edmonton in the Conference Finals behind a hot Mike Liut but then the impossible happened. Right from the ensuing faceoff after Reeds scored Willi Plett scored on a 75 foot slap shot. Liut was stunned. It effected him tremendously. After that goal he fought the puck the rest of the game. He was mentally shaken. The ONLY time I ever saw Liut mentally shaken ever. That goal caught him by surprise and it hurt him deeply upstairs in his head. When I saw him fighting the puck, you knew it was just a matter of time before the Blues would lose.
2. 1986 Game 7 against the Flames in the Conference Finals. Tough loss, can't really say the Blues got robbed in the game. Except Federko and Paslawski had a 2 on 1 in the opening minute of play and Jamie McCoun blocked Federko's pass. Had the Blues scored on that play, who knows???
3. 1996 Wings Game 7, I still see Shayne Corson breaking in all alone in the 1st OT, when that was happening I'm thinking to myself, this is the highlight goal. This is it.......well no, it ended up being Steve Yzerman's goal. Ouch. Got to give Jon Casey credit, he played great in goal that post season.
Now for my ultimate biggest blow to the Blues organization, for me, it's Detroit's owner stealing Jacque Demers from the Blues. Had Demers stayed with the Blues, there's no doubt in my mind the Blues would of had a dynasty. Despite being forced to trade away Joe Mullen, Doug Gilmour and Mike Liut, by 1990, the Blues were the best young team in hockey. They were on the cusp of greatness in 91. But Blues ownership undermined Ron Caron and personnel decisions were made beyond his control ( traded #1 for Rich Sutter, traded away Courts/Ronning/Mommesso for Butcher, traded Brind A Mour for Ron Sutter, signed Brendan Shanahan against his wishes due to possible repercussions and boom, we loose Scott Stevens) These personnel goofs derailed the Blues. Had Demers remained Blues coach, Demers and Caron would of been an exceptional tandem. Demers would of let Caron do his job, and harmony would of been abound. I truly believe that. It would of been a yearly show of conference finals and Stanley Cup appearances for a number of successive years, maybe as many as 8 or 9 in a row. No doubt in my mind the Blues would of grabbed 1 or 2 Cup titles between 91 and 95. Look at the teams who won went to the Cup those years - the hawks, Stars, Canucks......please. The Blues goofed. Losing Demers robbed this franchise of their destiny. And yes, I hate the Wings for this.