But there was also an unmistakably awkward feeling as well.
That's because O'Keefe has been quietly shown the door at the Swans, rather than voluntarily closing it himself.
At the start of 2014, O'Keefe said age was "just a number" and backed himself to keep playing for some time.
He also had his eyes firmly on 300 career games.
That hasn't proven the case, however, with O'Keefe stuck on 286 games since his final senior appearance against North Melbourne back in April.
He has done virtually all there is to do in a stunning career, winning two flags, a Norm Smith medal, an All Australian jumper and a best and fairest award.
He comfortably holds a place among the most influential and successful players in South Melbourne/Sydney Swans history and coach John Longmire was effusive in his praise of O'Keefe on Thursday.
But all the while, there was an uneasy feeling as O'Keefe addressed the media for the first time in months.
Demons door ajar
It became clear during the season O'Keefe was no longer in Longmire's plans and the midfielder gave a glimpse into the tension that decision had clearly caused between the two.
"We spoke a lot during the season," O'Keefe said of his head coach.
"We agreed to disagree on a few occasions.
"But I fully understand where everyone's coming from and I'm going to leave the Swans this year feeling good where the place is at and what I've achieved.
"I just really wanted the opportunity to thank everyone."
O'Keefe will get that chance on Saturday when he does a lap of honour around ANZ Stadium at half-time of the match against Richmond.
Ex-teammates Jude Bolton, Lewis Roberts-Thomson and Marty Mattner have all taken a similar walk in recent times, but those three retired knowing they had nothing left.
With O'Keefe, that decision is yet to be made.
There was an outpouring of relief and gratitude from Swans fans on social media after it was announced he would get his lap of honour and they would get a chance to say a proper farewell.
But the same sentiment wasn't palpable during Thursday's press conference.
Longmire tried to lighten the mood by joking the Swans "won't have to take the scales on interstate trips anymore", a reference to fitness fanatic O'Keefe's preference to weigh his food.
But it drew only a few chuckles, and a small grin from O'Keefe.
When a journalist asked O'Keefe about his career games and mentioned the number 282, he quickly chimed in with "286 mate. Don't cut me short".
It seemed to emphasise the unshakable perception O'Keefe believes the club has cut him short.
After the press conference, O'Keefe and Longmire shook hands, but there was none of the applause from his teammates in the room that greeted players such as Bolton and Tadhg Kennelly when they retired.
It's probably because O'Keefe doesn't yet know if this is the end and plans to gauge what interest there is from other clubs.
Longmire was asked whether O'Keefe could still contribute to another team.
"Ryan will obviously make that decision at the right time," he said.
"I'm not here to talk about that. I'm here to talk about what Ryan has done for this footy club."
It was a fair response, but it only served to add to the air of unease.
O'Keefe's former coach Paul Roos, now at Melbourne, said on Thursday it was probably a year too late for his club to recruit the veteran.
Cross-town rivals GWS won't be enquiring about his services, while he has an interest in coaching if his playing career comes to an end.
"The hard part is letting go," he said, "but that's just the life of footy or professional sport.
"You're not owed anything or belong to anything, you just pass through and hopefully you've left your mark on the place."
Of that, there can be no doubt.
Twitter: @AFL_JD