Since it's all pointless speculation at this point, I'll stand by my original assumption about the O'Reilly offer -- It was all a ruse where the Avs and O'Reilly had hit a wall in their negotiations and the relationship had soured to the point where the player wasn't willing to budge, so Sherman secretly asked Feaster to give the offer sheet within parameters that the Avs were willing to match.
Remember, the Flames and Avs were playing in Denver that night and the Avs announced they were going to match almost instantly (I think it was before that night's game had even started).
In exchange for doing him the favour, Sherman agreed to help out Feaster at some future point. Unfortunately, Sherman got fired before he could pay up. Or maybe, the handshake deal rolled over to Feaster and Sherman's replacements and that's why the Avs inexplicably gave up a 2nd round pick for Berra.
Another reason why Feaster was willing to play along is the Flames and Avs were both near the bottom of the Western Conference standings at the time, so helping get O'Reilly signed and playing in Colorado would hopefully make the Avs better enough that they wouldn't have a chance to get MacKinnon (oops!).
That's why Feaster wasn't worried about the whole waiver thing or losing the compensation, he knew the Avs were never not going to match the offer. Everything he said afterward was just CYA to avoid any blow-back from the PA for conspiring with another GM in that way.
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