The Chandler Jones Deal
The Raiders made another massive mistake when they handed troubled former Patriot Chandler Jones a massive $51 million extension. First, let’s caveat this by saying that neither McDaniels nor Ziegler could have known that Jones would again have serious personal problems, but it was possible. They couldn’t predict the future and that they’d cut the player.

That’s not why the deal was stupid but rather because they already had talent in Maxx Crosby. Meanwhile, Yannick Ngakoue was reliable on the other side of the line. Then they traded Ngakoue for the injury-prone Rock Ya-Sin. Jones became one of the worst free agents ever and affected the salary cap (via Heavy).