A veteran of 12 AFL seasons, Osborne has been re-cast as one of the Hawks' new kids this summer, thanks to his de-listing and re-drafting during the off-season.
The episode has ended well for the small forward, and he is now poised to add to his career tally of 161 senior games.
But it did bring with it a period of some uncertainty.
Although his de-listing was largely for list management purposes (in keeping with AFL rules, Hawthorn needed to create space on its list for three picks at November's NAB AFL Draft, plus it wanted to sign delisted free agent Jonathan Simpkin), there were no absolute guarantees Osborne would be reinstated.
A slower-than-expected recovery from surgery in May to repair torn anterior cruciate and lateral ligaments in his left knee had left him with work to do to show he could get back to pre-injury levels.
"With where I was at with my knee early on, after the operation I had some complications with my recovery, and you can get a bit down about things and a bit unsure about whether it's all going to work out," Osborne told AFL.com.au.
"I spoke closely with the club throughout the duration of my rehab.
"They wanted to give me every opportunity to get back, and I wanted to give myself every opportunity to be right and be confident in my ability to play another season.
"It (being de-listed) probably acted as another motivator to keep plugging away, get the body right, and get the knee strong again to get back playing.
"My dream job is to keep playing footy, so that was ultimately my goal."
Cut from the list at the end of October, Osborne continued his rehabilitation in the Hawthorn gym while his teammates holidayed, building strength back in his leg.
By the time draft night arrived on November 22, he had done enough to convince the club and himself that he was capable of playing on, and been given a commitment he would be taken with the Hawks' final pick, No.70.
Now it was just a matter of hoping no other team jumped in first, although at 30-years-old, that wasn't a major concern.
"I didn't have any interest from any other clubs, so I thought there was a pretty good chance [of getting through to the Hawks]," he joked.
Osborne didn't watch the draft, but got a phone call from Hawthorn advising all had gone to plan.
And then the flood of text messages started.
"All the new draftees' numbers get sent out to the playing list so that we can welcome them into the club, so I started getting texts from all the boys, because my number had been sent to them as the third pick," Osborne said.
"And the banter still goes on.
"The first year players, when they have extra meetings or work on their development, my name always gets thrown in there."
Osborne may differ from his fellow draftees Tim O'Brien and Kaiden Brand in that he's not dreaming of another ten years in brown and gold (he's been there and done that), but he plans on sticking around for a little while yet.
"I'd like to play for a few more years," he said.
"It's been year by year for the past few years, but as long as I'm enjoying it and staying fit, and playing good footy, I'd like to play for as long as I can."
Mark Macgugan covers Hawthorn news for AFL.com.au. Twitter: @AFL_MarkM.
