Jolly and Didak were both key players in Collingwood's first AFL premiership in 2010 since 1990 while Krakouer joined the Magpies in 2011 and played in the grand final of that year while Russell had just the one season with the Pies in 2013 after crossing from Carlton.
The move to delist ruckman Jolly was perhaps the surprise out of the four departures confirmed on Tuesday.
The 31-year-old came to Collingwood at the end of 2009 following 118 games with the Sydney Swans including the 2005 premiership and that was after a further 48 matches between 2001 and 2004 at Melbourne to begin his AFL career.
Jolly immediately cemented himself as the No. 1 ruckman at Collingwood in the premiership year of 2010 and continued to be one of the best big men in the competition over the next three years.
However, his body began to let him down during 2013 and even though he was back up and running in the VFL by the end of the season, Collingwood coach Nathan Buckley preferred first-year ruckman Brodie Grundy to him and Jolly was not selected for Saturday night's losing final against Port Adelaide.
In all, Jolly played 71 games with Collingwood to take his AFL total to 237 including being the No. 1 ruckman in two premiership sides.
He is believed to have been disappointed at the way he was treated, and not selected, in the latter part of the season by the Magpies and feels that he has something to offer another AFL club for another year or two.
One option appears to be a return to his first AFL club Melbourne where he will reunite with his premiership coach from Sydney Paul Roos.
The delisting of Jolly appears to open the door for Ben Hudson to remain for another year as a back-up ruckman to Grundy and fellow youngster Jarrod Witts, while also continuing to work as a part-time coach.
While the delisting of Jolly was somewhat of a surprise, the departures of veteran small forwards Krakouer and Didak were more expected and the departure of Russell is recognition that his recruiting from Carlton has not proved fruitful.
Didak's career at Collingwood is now over after 218 games and 13 seasons where he has been one of the most skilful, creative and mercurial players in the game, and one of the most popular Magpie amongst both his players and supporters evidence by his return late in the 2013 campaign.
The 30-year-old managed just 16 matches over 2012 and 2013, but does hope to revive his career elsewhere despite that now looking decidedly unlikely.
To go with his 218 games and 274 goals for the 'Pies, Didak played in five grand finals for the win in 2010 and losses in 2002, 2003 and 2011, and the draw in 2010.
He will always be grateful to Collingwood but doesn’t feel ready to retire.
"I'm not ready for retirement and the ride has another lap or two to go, I hope," Didak said.
"I've had an incredible time at Collingwood. We won a lot of games, won a premiership and I met some lifelong friends. I've got a lot to be thankful for and I know I'm going to miss playing in front of the black-and-white army. I owe them a lot."
Krakouer's three-year career with Collingwood ends after 35 matches including the 2011 grand final losing grand final to Geelong.
He originally played 102 AFL games with Richmond before returning to the WAFL with Swan Districts in 2008. However, that lasted just nine matches before he found himself in prison.
One of the most remarkable football stories was still to come, though, when he played the 2010 WAFL season back with Swan Districts leading them to a premiership while also winning the Sandover Medal and grand final Simpson Medal.
That saw him earn another chance with Collingwood in the AFL and he had an outstanding 2011 season but then needed a knee reconstruction on the eve of the 2012 campaign.
He was able to return for the finals last year but managed just eight matches in 2013 and now finds himself also delisted by the Magpies.
Meanwhile, Russell arrived at Collingwood this season after 116 matches with Carlton but he managed just nine appearances with the Magpies before now finding himself off the list.