Taken by Richmond with the 63rd pick in the NAB AFL Draft back in 2010, Derickx managed just two senior games in three years as a Tiger, with a broken ankle, a twice broken wrist and the emergence of Ivan Maric holding him back.
That's when the Swans came calling and from the moment coach John Longmire and recruiting manager Kinnear Beatson told him he would be replacing Shane Mumford, he knew it was the right move.
Left out of the team for round one, he got his chance the following week as Mike Pyke's back-up, and has since strung together seven consecutive games.
When Pyke suffered a hamstring injury in the first half of the round seven clash with the Brisbane Lions, Derickx suddenly found himself a first-choice AFL ruckman.
He has filled the role admirably over the past two weeks and will attempt to do so again against Essendon on Friday night.
"I love that responsibility and that challenge and think it brings the best out of a lot of players," Derickx told AFL.com.au.
"When Pyke went off injured against Brisbane, the runner came out and said, 'I've got bad news'.
"I was like, 'That's bad news for Pykey, but good news for me'. I love that sort of challenge."
Growing up in in tiny Dunsborough in Western Australia, 245km south west of Perth, Derickx passed his time surfing and playing a bit of footy, but "not taking it too seriously".
He then suffered his first major setback when, at the age of 18, he broke both the tibia and fibula in his leg in a tackle gone wrong, forcing him to miss nearly two years of football.
Undertaking a carpentry apprenticeship during his recovery, he then moved to Perth to play two years with Claremont in the WAFL.
Playing at that level helped his game enormously, while he also enjoyed another late benefit – a growth spurt that took him to 200cm and beyond.
Soon scouts were getting in touch about his AFL prospects and the mature-age recruit was snapped up by the Tigers, but his career never really got started at Punt Road.
"My three years at Richmond were injury plagued," he explains.
"First year I missed the whole season with a broken ankle, that put me on the back foot coming into my second year.
"I played two games that year and then the following pre-season I broke my wrist twice and missed the first five games or so, and that just put me in the scrap heap.
"Pretty early on I think the club and I knew I'd be moving on at the end of last year, which was fair enough.
"There are no hard feelings there."
He began making plans to move north to study construction management and play a bit of football with Sydney University.
Instead, he signed with the Swans, the latest in a long line of players to enjoy a career revival with the Harbour City club.
The Swans were an interesting destination for a man who grew up a staunch West Coast supporter during the heart of the fierce rivalry between the two teams that culminated in the epic Grand Finals in 2005-06.
He went to the 2006 qualifying final in Perth when Michael O'Loughlin's late goal and celebration right in the face of an Eagles cheer squad member sealed their victory.
"I was there that day sitting about 10 metres from that guy in the crowd," Derickx said.
"I was a massive Eagles supporter back then and loved that rivalry, and obviously wasn't a huge fan of the Swans.
"Now I'm wearing (O'Loughlin's) number.
He has settled well into life in Sydney and his efforts are catching the eye of his teammates.
"Last week (against Hawthorn) he was outstanding," midfielder Luke Parker said.
"He's just playing pretty basic footy. His effort and follow-up are similar to probably Shane Mumford's role last year.
"He's come in and given us that extra midfielder role and I just think his aggression really lifts the team."
Through his various trials and tribulations, Derickx says he had to work on the mental side of his game as much as the physical, but never lost faith in his ability to make it at the highest level.
Being told he would be replacing Mumford also did wonders for his confidence.
"Even being thought of as a replacement for a ruckman of that calibre was confidence boosting," he said.
"Now I'm hoping to cement my spot."
Derickx also experienced another first following his move to Sydney – becoming tabloid fodder.
The 26-year-old was with Lance Franklin and two Swedish girls at Bondi Beach earlier this year in a moment that caught the attention of the paparazzi.
"We were down just having a swim," Derickx said.
"It was a bit unlucky for Buddy, but it was just a casual day down at North Bondi.
"I couldn’t believe it. I didn't mind it as much as he did."
Twitter: @AFL_JD
