Ben Ross instantly comes to mind. A quick browse of his Wiki page says he played 42 games for us in 4 seasons, at $400,000 a season, so roughly $38,095 per game.
However, it wasn't for lack of trying. He had a horrible, horrible run with injuries during his time with us and his lack of value for money wasn't as a result of him putting his feet and up not having a go. It was all beyond his control.
Darren Albert was a shocker. The bloke could go at a hell of a rate of knots, but just had no direction other than straight forward. A left or right turn was completely beyond the scope of his skill set.
Vagana went to sh!t when he arrived too, and while I don't think he was entirely happy at the Club but stuck round for the pay cheque, I'll concede he didn't get the quality ball he got at the Bulldogs.
I don't think Filiga is a candidate. We tried, we failed, and he only got away with under $150K for his two years of f-ck all from what I understand. Weight that up with what he potentially should have become and I still think it was a worthwhile gamble.
Chris Anderson and most of the useless f-cks he brought with him, in combination with the talent we let go is right up there too.
Bit hard to go past Tony Zappia given how extensive the amount of damage he did in such little time, although I tend to think he was just the straw that broke the camel's back in a clusterf-ck of incompetent administration that dated way back to before his recruitment.