Trading Charlie Joiner in 1976
The easiest entry on this list involves the trading of Charlie Joiner.
Joiner was a fourth-round pick by the Houston Oilers in 1969 and found his way to Cincinnati in 1972. From there, he mostly served as a third-string wideout for the Bengals and the team ended up sending him to San Diego in exchange for Coy Bacon and a first-round pick.
Well, as we all know, Joiner went on to do in San Diego and he did it as early as his first year with his new team. He went for over 1,000 yards receiving in 1976 and made it to the Pro Bowl. He spent the final 11 years of his career with the Chargers and finished it up with 9,203 receiving yards and a trip to the Hall of Fame in Canton.
Meanwhile, Bacon was only in Cincinnati for two years and the first-round pick turned into William Brooks, who spent just four years with the Bengals and only six years total in the league.
The Bengals gave up on Joiner way too soon and weren’t using him the right way. He was a Hall of Fame wide receiver who could have been a bright spot for this team for over a decade but instead, he merited two disappointing players in return while he went on to shine in San Diego.
This is easily the worst and most disappointing trade the Bengals have ever made.