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.
One man's trash is another man's treasure. The Demons struggled to find a suitable role throughout Dunn's career at Melbourne.
Starting his football career as a tagger after going 15th in the 2004 draft, Dunn was soon moved both forward and back and struggled to cope under frequent changes in coaching at the Dees.
Dunn finished his career with the Demons playing a majority of his games for Casey Demons, before being traded to Collingwood in the 2016 trade period with pick 51 for the Magpies' third-round pick.
Dunn's career to date with Collingwood has seen a rejuvenation in defence under Nathan Buckley and now features in the Magpies' leadership group.
Time will tell for Jesse Hogan's career. The big-bodied youngster kicked 152 goals in his five seasons including winning the rising star award in 2015 with Melbourne, but has had his career constantly interrupted with off-field issues.
In the short term, the Demons have struggled for goal kickers to start their 2019 campaign, with a 3-7 record and a miserable 99 goals from their first seven matches.
Melbourne sent Hogan to Fremantle in exchange for picks 23 and 6, with the latter being moved onto the Gold Coast for Steven May and Kade Kolodjashnij. The Demons' decision to send Hogan home will be heavily weighted by the performance of those recruits and if Hogan can find his form in the west.
Prior to exercising his rights in free agency with a move to Hawthorn in 2014, Frawley was named at back-pocket in the 2010 All-Australian side and grew into a key role in Melbourne's improvement under Paul Roos.
Unfortunately for the Dees, Frawley walked to the Hawks and was a premiership player in less than a year's time. Under Alistair Clarkson, Frawley found a reinvigorated position as a defender and became a cog in Hawthorn's three-peat.
Luckily for the Dees, the club was compensated with pick three in the 2014 draft, leading to the selection of jet midfielder Angus Brayshaw.
Howe was awarded Melbourne's best first-year player in 2011 and led the club's goalkicking in 2013 with a total of 28. Not an outstanding feat, but it shows where the club sat.
Since moving to Collingwood in 2015, Howe found his calling as a rebounding half-back for the Magpies and became an instrumental player in their push for a premiership.
Howe's high-flying agenda hasn't slowed down since leaving Melbourne, as he has seen a vast improvement in his overall game since moving to his second club with a +5 difference in disposals per game.
Another Demon who struggled to find his calling during the start of his career with Melbourne. Martin's breakout year with the Demons came in 2011 as he took one the number one ruck position in the absence of Mark Jamar.
A hip injury riddled Martin's 2012 season, added to the return of Jamar, limited to Martin's season to just seven matches.
In October that year, Martin was traded to the Lions for picks 52 (Matt Jones) and 71 (Daniel Nicholson) and was crowned joint Brisbane Club Champion in 2015 with Dayne Beams, Dayne Zorko and Mitch Robinson.
Martin's move to Brisbane opened the floor for now 2x All-Australian Max Gawn at Melbourne, leading to many 'what ifs' for both clubs if he remained in Victoria.
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.
Jolly managed to play out just the 48 matches for Melbourne, fighting for time in the ruck against Jeff White. The Demons traded Jolly in 2014 for the 15th overall pick (Lynden Dunn) to Sydney, where Jolly became a vital asset in a ruck partnership with Jason Ball for the Swans' premiership in 2005.
Jolly missed just two games for the Swans and was eventually traded to Collingwood in 2009 following a request to be with family in Victoria.
For the second time in his career, Jolly won a premiership in his first season with a new club, playing as the Pies' No.1 ruckman in their replay grand final win over St Kilda.
Jolly was delisted in 2013 by Collingwood, finishing his 237 game career with two premierships.
Thompson's career with the Demons began on a flyer, crowned Melbourne's best first-year player having debuted at 18-years-old. Subsequent injuries halted Thompson's progression, struggling to return to the first team and eventually requested a trade to South Australia to be with his unwell brother. Melbourne received pick 12 in the National Draft, leading to the selection of Nathan Jones.
Thompson kicked 27 goals in his first season with the Crows and by 2007 finished equal 7th in the Brownlow with 18 votes.
In 2011, Thompson won Adelaide's best and fairest and polled the second most disposals in the league, including 51 touches against Gold Coast, falling two possessions short of Greg Williams' 53 touch record.
Thompson followed up his historic season with an All-Australia selection, a second Best and Fairest and a fourth-placed finish in the Brownlow.
Thompson announced his retirement in 2017, ending his illustrious career with 308 games (39 Melbourne, 269 Adelaide) and 155 Brownlow votes.