Baltimore Ravens: Failing to Trade for Derrick Henry
The Ravens regret differs a bit from the rest of the list because the Titans said they weren't going to trade Henry. However, this was only stated a few days before the Trade Deadline, and it's possible they were listening to offers but didn't like what they were hearing so decided to hold onto him. After trading away Kevin Byard last week, it's hard to imagine there was no deal that they would have accepted for Henry.
And if any team was going to trade for Henry it had to be the Baltimore Ravens. Baltimore lost J.K. Dobbins to a torn ACL during their week 1 game, and it left the team pretty thin at running back. Dobbins is a free agent after this season, and it's very possible the team won't bring him back to to his extensive injury history. In his absence, Gus Edwards and Justice Hill have been carrying the load for the Ravens at the running back position. While they have been solid, the team can certainly do better.
Lamar Jackson's best season came when he had Mark Ingram and a rookie J.K. Dobbins in his backfield alongside him. The trio was so dynamic that defenses had no answer for them. Derrick Henry would've given Jackson the best running back he'd ever played with and would make it impossible for teams to put all of their focus on him.
Trading a second round pick and a late round pick for a running back isn't usually the best move due to the short shelf life at the position but in this instance, it would've been the right move. The Ravens are also in win now mode, and failing to make a move that would've terrified their opponents and made them impossible to game plan against, is one that they will regret.
Only time will tell which of these teams will regret not making these trades the most, but one thing is certain, this division is the most competitive in the league, and none of these teams making a move to push them over the top could come back to bite them.