The Pies have been one of the better clubs over the last two decades. But that doesn't mean they haven't had their fair share of let downs.
From draft busts to underwhelming recruits, injury prone players and everything in between, sometimes it just doesn't work out.
Here are Collingwood's worst 22 of the last 15 years:
Back pocket: Ben Sinclair
Sinclair was one of Nathan Buckley's favourites, and his pace was a real highlight. But injuries and an inability to lock down a role up forward or down back led to his downfall.
Full back: Jordan Russell
Russell arrived at Collingwood at the end of 2012 after struggling for opportunities at Carlton despite some solid years in 2009 and 2010. Unfortunately, his best footy was well and truly behind him at that stage, only managing nine games in his sole season in black and white.
Back pocket: Adam Oxley
Every Pies fan will remember Oxley's outstanding Queen's Birthday performance in 2015, where he racked up 30 disposals and clunked 15 marks. He showed great potential that season of becoming a quality half back, but went backwards the next two seasons before getting delisted.
Half back: Julian Rowe
Rowe was picked up by the Pies at the 2003 AFL draft and showed all the potential in the world, establishing himself as a regular in the side in 2005. He was dropped by the end of the season and after playing just two games in 2006, got delisted.
Centre half back: Danny Stanley
Stanley was taken with pick No. 21 at the 2005 AFL draft and the Pies generally maximise top 30 selections. Well, Stanley only ever played five games at the club before departing for the Suns in 2011.
Half back: Jackson Ramsay
Ramsay was the answer to the Pies’ lack of drivers off half back before Brayden Maynard and Jack Crisp were a thing. Injuries may well have been the biggest roadblock to the Western Australian's career, plagued by shin and wrist issues before rupturing his ACL.
Wing: Sam Iles
The Pies nabbed Iles with pick No. 2 in the 2006 pre-season draft, who showed signs of becoming a quality midfielder at a young age. He never cracked a permanent gig in the senior team and got delisted in 2008 before joining Gold Coast a couple of years later.
Centre: Ben Kennedy
A guy who could dominate at VFL level but not in the senior ranks, Kennedy never made good of his AFL opportunities in a time when the Pies were crying out for development from their younger players. The former pick 19 was traded to Melbourne at the end of 2016.
Wing: Simon Buckley
Buckley had his moments at the Demons and could have been a steal for the Pies, who grabbed him in the 2009 AFL draft with pick No. 85. He played 26 games in the black and white stripes but never developed as the club would have liked.
Half forward: Chris Egan
Egan could be the biggest let down of all Magpies over the last 15 years. Taken with the 10th overall pick in the 2004 draft, he played 13 games in 2005 and looked like a player. Egan mustered just 11 games the following season before falling into oblivion, getting delisted in 2008.
Centre half forward: Quinten Lynch
Lynch was the Pies' first ever 'big' free agent signing, joining Nathan Buckley's side on a two-year deal as the retiring Leigh Brown's replacement. The former Eagle only booted nine goals from 18 games and failed to have an impact elsewhere.
Half forward: Patrick Karnezis
Originally drafted with pick No. 25 by the Lions, the talented Karnezis joined Collingwood in October 2013 and gave fans plenty to be bullish about. He showed great form in the VFL but could never crack the senior side despite their struggles over 2014 and 2015. It was a weird scenario where there seemed to be something more going on behind closed doors.
Forward pocket: Alex Fasolo
Fasolo burst onto the scene in 2011, playing in a Grand Final and looking like the future of Collingwood's forward line. Unfortunately, he was never able to consistently produce, with his best goal-kicking season being a 28-goal campaign in 2017. The Western Australian moved to Carlton at the end of last season as a restricted free agent.
Full forward: Jesse White
White joined the Pies in 2014 after a career-best season at Sydney. Recruited to partner with Travis Cloke up forward, White's best season goal kicking tally in black and white was 27. He retired in 2017.
Forward pocket: Sean Rusling
Rusling was a prodigy for Collingwood's forward line, boasting elite pace and a knack for kicking goals. The key forward's body let him down, retiring in 2010 after being hampered by a host of injuries throughout his career.
Ruck: Cameron Wood
Originally a top 20 pick at Brisbane, Wood joined Collingwood in 2008 as one of the most promising young ruckmen in the game. Wood never became the dominant big man the club had hoped and the acquisition of Darren Jolly limited his opportunities, fleeing to Carlton in 2014.
Ruck rover: Shane Woewodin
Woewodin was traded to Collingwood from Melbourne for a first-round pick at the end of the 2002 season. The gun midfielder failed to return to his 2000 Brownlow-winning form, never averaging more than 19 disposals in his three seasons at the Pies.
Rover: Clinton Young
The 2008 premiership Hawk signed a three-year deal with Collingwood from the 2013 season but never really got going at his new club. Injuries also slowed Young down and he was delisted at the end of the 2015 season.
Brad Dick
Dick could have been one of the better small forwards in AFL, boasting elite speed and an ability to kick goals. He booted 22 goals from 16 games in 2009 but injuries cruelled the rest of his career.
Jackson Paine
There were big wraps on Paine within the club in their ever-lasting search to pair a quality key forward with Cloke. He wasn't able to fill that role, totalling just six games at Collingwood before getting traded to Brisbane at the end of 2013.
Corey Gault
Much like Paine, Gault was another exciting key forward on the Pies' list around that 2013 period when they were crying out for some tall timber in attack to assist Cloke. He looked like the real deal after a strong 2016 pre-season, but only played the opening two games before getting dropped and then delisted at the end of the season.
Tom Davidson
Recruited from the Geelong Falcons in 2001 with pick No. 27 in the draft, Davison was touted as the club's next gun key forward. But two serious knee injuries hampered his development, playing just two games for the club before getting delisted at the end of 2005.