3. Trai Turner trade
While he does not make many trades, Tom Telesco still finds himself on this list. And this is not to bash Telesco and say that he made a bad trade when he traded for Trai Turner. When it happened, every single Chargers pundit out there was raving about how good of a move it was.
The Bolts flipped one guaranteed year of Russell Okung for two potential years of Trai Turner. The Bolts had plans of signing a free-agent tackle in the offseason (Bryan Bulaga, who has also been disappointing) and thus flipped the tackle for more guard depth.
Turner had multiple Pro Bowls coming into the Bolts and was viewed as an improvement on the offensive line. However, if you looked past the Pro Bowls you would have seen a concerning trend with pressures before the Panthers traded him.
Turner could hardly stay healthy with the Bolts in 2020 and when he was healthy he was really bad. Turner was not the offensive line improvement that the Chargers were hoping for and instead held the team back from having a good offensive line.
The Chargers parted ways with Turner after the 2020 season with no dead cap owed with the taste of disappointment in their mouths. It did not hurt the Chargers, as they did not lose much in Okung, so it is hard to call it a bad trade.
However, with the expectations that the team had for Turner, it certainly was a disappointing trade.