Melbourne is still looking for their first grand final appearance since 2000, although despite falling one hurdle short in 2018, look to have taken a step back this season.
The Dees are 3-7, and have been a shadow of the side that willed their way to a preliminary final last year.
The club has turned over list after list since 2000, and while many of the decisions they made on players were the right ones, these eight below have certainly come back to hurt them.
3. Tom Scully
Taken first overall in the 2009 draft and given club legend Ron Barassi's cherished No.31 guernsey, pressure had mounted onto Scully's shoulders before his first game for the Demons.
Scully took out Melbourne's Harold Ball Memorial Trophy awarded to the Demons' best first-year player ahead of No.2 overall pick Jack Trengrove. Scully also placed second for the NAB Rising Star Award behind Sydney's Dan Hannebery.
Scully's contract ended after two seasons with the Dees and eventually signed for expansion club Greater Western Sydney for a lucrative deal estimated at $6 million over six years. The Demons were compensated with picks, trading for Dominic Barry and selecting Jesse Hogan.
Scully played a vital role in the Giants' 2016 and 2017 finals series and finished the 2017 season with a second career All-Australian nomination while proving to become one of the greatest endurance athletes in the game's history.