Thought I'd try something different here and see who is willing to share something about their experience as a GZL General Manager with the rest of the community. I think we can all look back on our decisions and pick one that stands out as the one we regret the most. Whether it's trading someone out, not trading someone in, missing an important part of the offseason, moving teams, not moving teams, leaving the league and coming back, it could be anything that in hindsight you wish you'd done differently.
I'm willing to share my biggest regret to date and hope others are willing to add theirs:
In the offseason of 2017 the draft class had some exceptional talent that we wanted to get a piece of. As we had traded our first of that year in the previous years deal to get RG3 we were low on ammo to make a play, so we put CB Camden Pietarila on the block and eventually dealt him to Dallas for the 6th overall pick. We thought this value was right for a player of his talents (having drafted him at 12 and progressed him to mentor status within 2 years) and we were hoping to get an even better talent with this pick. Looking back now it was a mistake to trade out our best corner in an effort to get a 6'7" receiver (Drogan) or a 6'4" corner (Stonewall) in the draft, especially with the efforts we'd put into Pietarila already. Stupidly I even didn't try to one-for-one Pietarila for another corner like Stonewall, but traded down to picks 11 and 12 thinking that someone would fall that far (based on all the mock drafts). So even though I ended up with LOLB Khalil Mack and LT Greg Robinson from that draft I severely hampered our secondary in the process which is a move we're still trying to overcome to this date. The main reason I thought we could justify moving Pietarila was because I thought his strength was a factor in his poor return of deflections to catches allowed and interceptions, but I've since realised those factors are largely affected by playbooks and play style, not just a minor attribute like strength, so I'm kicking myself for making this move and will continue to do so until we've finally got a solid pair at corner we can rely on.