9. The super-random Dekoda Watson trade in 2016
There are very few things more frustrating than having to trade NFL draft capital for special teams help. Trading for Dekoda Watson in 2019 was a very curious move, indeed.
For some context to this move, the Denver Broncos had pried Rich Scangarello away from the San Francisco 49ers in the 2019 offseason to be their offensive coordinator. The Broncos had clearly realized their mistake in not hiring Kyle Shanahan in 2017, so they wanted whatever piece of his coaching tree they could get. After initially being declined an opportunity to poach Scangarello, the 49ers finally relented.
The Dekoda Watson trade felt very much like the Broncos were paying up for the 49ers allowing them to hire Rich Scangarello, and that may have been the case. With all due respect to Watson, who played in the NFL from 2010-19, this was a non-sensical trade from the very beginning. The Broncos sent a 5th-round pick to the 49ers for Watson, and that 5th-round pick ended up being used on linebacker Dre Greenlaw.
Now, 5th-round picks don't always work out, but that one is brutal in hindsight. Greenlaw has become one of the NFL's best linebackers while Watson didn't even make the Broncos' roster in 2019. He had only suited up for four games the year prior. It's a good thing most people don't know that the pick used to trade for Watson ended up being spent on Greenlaw.
I guess they know now.