Waiving Ray Sheppard because he wasn't a defensive gem. All the guy does is score goals, why the hell would that be important?
Acquiring Real Cloutier. Another freaking dud, though there was scuttlebutt that Bowman had a pet hate for Cloutier going back to Scotty's Hab days and he made sure to run Cloutier out of the league when he had a chance. Too bad it cost him so damn much to carry out a vendetta -- JF Sauve seemed to kill the Sabres for years in the playoffs, let alone them losing LW scoring for seemingly ever with McKegney gone. The Nords so often seemed to have the Sabres number, the last thing they needed were more guys to tune them up and Bowman gave them to them. Perhaps part of why I don't like the "Spezza for a pile of Sabre stuff" proposals (that and not thinking Spezza is that much of a difference maker to warrant the sort of return, given his health, production, and playoff disappearences... any Tim Connolly type can rack up points on cellar dwellars and lottery teams and that is my preception of Spezza. When the going gets tough, Spezza sprains his spine.)
Dealing Alan Haworth to the Caps to make sure they didn't draft Phil Housley. They had no intention of taking Housley, instead, they took man-beast Scott Stevens, the guy they wanted all along. Yeah. Well done Scotty.
Ray Shepard - outscored (goals) Pierre Turgeon his rookie year, IIRC. Always liked him.
Real (not my) "Buddy" Cloutier - would be the #1 move on my list.
And I forgot about the backfired subterfuge with Haworth.
Not quite in line with the thread but I can't help thinking about it with the news from Russia. There are always guys in the draft who I really wanted to see Buffalo select, but they didn't. Among them: