1. Players taken after
You always hear fans complain about Mahomes and Trubisky, but the Chicago Bears took Adam Shaheen over George Kittle. Sure, Kittle went a few rounds later, but many were privy to how good Kittle could be pre-draft. He was known as a great blocker, and his combine was elite.
Also, while you can say that many missed on Kittle, not many teams took a tight end over Kittle, and only one team took the kid from Ashland, over the athletic marvel from Iowa. Beyond that, small school tight end Jonnu Smith went after Shaheen too. Both would have made huge impacts on the Bears roster.
As noted, the position can change as well. Joe Mixon, Alvin Kamara, JuJu Smith-Schuster, Cooper Kupp, Kenny Golladay, Chris Godwin, and Taylor Moton all went after Shaheen. All would have been huge hits that could have impacted the Bears. Also, for Mixon, Kamara Smith-Schuster, and Godwin you have pedigree players from big schools with big performances on their plate. These were known prospects.
Overall, both were misses. However, for the value they got, the players they passed on, and the complete whiff on the position as a whole, it has to be looked at that Adam Shaheen set the Bears back more than Mitch Trubisky did.