Fortunately for Playfair and the Swans, the answer was a resounding 'yes'.
He was selected by the club with its first selection (No.10 overall) in Tuesday's NAB AFL Rookie Draft and told sydneyswans.com.au of his relief immediately afterwards.
"I had high hopes coming up here of restarting my career and making a long career in Sydney and to be injured from pretty much day one, for two years, was really disappointing," Playfair said.
"Then to go through operations that hadn't worked, while my contract was running out, it was really frustrating and pretty hard to deal with at the time.
"Even coming back, I was having thoughts about whether I wanted to sign up for all this again and possibly get injured.
"But in that time, I really found my love of football and I didn't come back for anything else other than that I want to play and get the best out of myself. That's what's been keeping me going."
Chronic hamstring pain limited the former Geelong tall to just 11 games in his two years at the Swans, all of which came in 2008.
With his contract expiring at the end of October, Playfair was delisted, but not cut adrift by the club.
The 26-year-old was offered the opportunity to continue training in a bid to prove his troublesome hamstring could withstand the rigours of playing AFL.
Playfair said it wasn't until two weeks before Tuesday's rookie draft that he was confident of remaining at the club.
"I've been talking to Roosy a fair bit over the last three months, just on and off about how I was going. Initially he said it was a bit of a long shot, but they would just see how my body went," he said.
"In the past couple of weeks, the coaches have been saying they've been happy with me and it looked like my footy was going okay.
"They told me that if I held up until [the draft], it was looking pretty good."
Playfair said as his recovery from the radical surgery progressed, it became a mental challenge as well as a physical battle.
The operation involved slicing his hamstring tendon in half at its upper attachment and stapling it to the bone, securing the tendon and freeing the associated nerves that were causing him so much pain.
"There have been a couple of sorenesses here and there, which have been normal when I've been getting back into sprinting," he said.
"I got a bit worried about it but my relationship with the physio and with Roosy really helped me in that sense, because the physio said they expected all this and it was normal.
"The more sessions I've done, the more confident I get. I've been 100 per cent training for pretty much two months so I've got a fair bit of confidence in the leg now."
While his fitness is rapidly returning, the 198cm forward said his skills had been very rusty after more than a year away from training drills with his teammates.
"I hadn't done a skills session for about 15 months and the first one I did was pretty light," he said.
"I was pretty nervous and I stuffed up a couple of drills - really basic ones which I didn't do that well. But it was nerve-racking and exciting at the same time."
The Sydney Swans playing list was finalised on Tuesday and the Swans want to make sure you're also part of the team. To join up, or to renew your membership, please go to sydneyswans.com.au/membership, or phone 1300 663 819.
