Like others here, I've been following the team closely since Day 1. I'll go way back to a few that I was really wrong about.
Bryan Helmer was an undrafted defenseman. I saw him in some games in 1998-99, and insisted he was going to be a star. During the next ten years, he played 146 NHL games.
The Coyotes drafted Ossi Vaananen in the second round, and I was excited about his skating finesse. He carved out a decent NHL career, but wasn't anywhere near the #1 D guy I predicted he'd be.
And to this day I don't know why I was happy at the time that we gave up on Danny Briere at the deadline. Ugh, Chris Gratton in return.
In case you're not as well-versed in ancient Coyotes' history, you'll recognize the name Rick Tocchet. It was evident to me that his game was tailing off, so I was pleased with the deadline deal in 2000 with the Flyers for anyone. It ended up being 15 games of Mikael Renberg, but shedding Tocchet at that time was the right move. So that take was a win, sort of.