Act one was set in Sydney, where the midfielder's attacking style didn't fit the Swans' lockdown gameplan, and he departed after two years without a senior appearance to his name.
Next it was back to Colac, and countless drives between his hometown and Geelong, where he sought to rebuild his career via the Cats' VFL team.
Then finally, or so it seemed, to the Geelong rookie list, and at last, six years after he was first drafted, to an AFL debut.
But just when the rewards for persistence and hard work seemed set to flow, another twist – despite having been in the Cats' best 22 for their elimination final loss to Fremantle last September, there was no room for Simpkin on the club's list of 44 just two months later.
Delisted again, but snatched up by Hawthorn, the midfielder now stands on the cusp of breaking into coach Alastair Clarkson's line-up for the round one clash with his former team at the MCG on Easter Monday.
A poised 18-disposal NAB Cup performance against Richmond in Launceston on Saturday has almost sealed it.
"It has been a pretty long road, but hopefully this year I can play a few games and it will make it all worthwhile," Simpkin told AFL.com.au this week in the lead-up to Saturday's match.
"I don't get too disappointed now about little hurdles – I just control what I can control.
"You just go out there and train as hard as possible, and work on areas you need to work on, and hopefully you might get the reward."
Rather than boarding a plane to Tasmania in a brown and gold tracksuit on Friday, Simpkin could just as well have been working away on a building site in Colac.
Setbacks do take a toll on an individual's drive to succeed, no matter how resilient they may be, and the country boy reached a fork in the road at the end of 2009.
He'd spent two seasons playing partly with Geelong in the VFL, and partly with his mates at home.
Life in Colac was good, and the path back to the big league looked long.
"I played six or seven games for Colac in 2009, and was sort of half-and-half – I didn't know whether I wanted to be at Colac or Geelong," he said.
"At the end of 2009 I decided I'd put everything into Geelong for the next season.
"I ended up having a pretty good year and got picked up by Geelong (in the AFL) because of it.
"It's probably the best decision I've made. I'm glad it worked out that way."
Simpkin's axing by the Cats didn't come as a complete shock.
He'd played four senior games and also picked up a second VFL club best and fairest, but an AFL rule change meant rookie lists had to be cut from six to four.
Geelong decided to promote Jesse Stringer to the senior list, and retain George Burbury, Cam Eardley, Jackson Sheringham and Josh Walker as rookies.
That left Simpkin on the outer.
Thankfully, Hawthorn had sensed what was coming too, and got in contact with the 25-year-old even before the Cats announced their decision.
"In the end I'm sort of glad it happened," Simpkin said.
"I ended up on a senior list here at Hawthorn, and there were only rookie spots available at Geelong.
"So it's probably worked out better."
Simpkin has settled in well at Waverley.
He has trained hard over summer, and teammates have commented on how quickly he has picked up the club's gameplan.
He is living with Luke Breust, a premiership teammate in the Swans reserves in 2007, while his captain, Luke Hodge, is an old Colac acquaintance, the pair having attended the same primary and secondary schools.
Brother Tom is just down the road at St Kilda.
He keeps in touch with his former Geelong teammates too, although if Clarkson has any hopes of gleaning tactical information via that connection, he can forget them.
"I speak with them every now and then, but not really about footy," Simpkin said.
"They're pretty tight-lipped now.
"I think Joel [Selwood] got into a few boys and told them not to let anything out, so they don't tell me too much."
A Hawthorn debut against the Cats would be fitting, but Simpkin isn't dwelling on the prospect too much just yet.
Rather, he's sticking to the philosophy the years of ups and downs have taught him.
"I'd love to be there, of course," he said.
"It'd be great to play on the MCG against Geelong first up, but that's out of my control.
"All I can do is try to put my hand up by playing well in the NAB Cup, and hopefully the coaches see enough to want to pick me."
Jonathan Simpkin is a midfielder in AFL Fantasy. He averaged 38 points in 2012. Register your team at our AFL Fantasy Hub.
