O'Keefe started the year fourth on the Swans' games-played list with 282 appearances and with every intention of chalking up 300 games and potentially playing on in 2015.
But the year hasn't panned out as he would've liked. He has played just four senior matches to start the season and has found himself stuck in the reserves ever since.
With eight matches remaining in the home and away season and a maximum four finals after that, it seems the off-contract 33-year-old's hopes of becoming the fourth Swan to reach 300 games has passed him by.
Younger Swans such as Luke Parker, Jake Lloyd, Harry Cunningham, Brandon Jack and Zak Jones have overtaken O'Keefe in the pecking order.
Making it harder for the former All Australian and best and fairest winner is the form of the senior side, which has reeled off 10 consecutive victories since his last senior game, the defeat to North Melbourne in round four.
But Longmire certainly isn't writing O'Keefe off and says it's critical the veteran maintains the best possible form in the seconds.
"I continually talk to Ryan and it's a week-by-week proposition," Longmire said on Monday.
"It's obviously been tough to this point because our players have been playing pretty well and been pretty consistent. What happens from here I'm unsure.
"Things do change pretty quickly. I'm sure Jake Lloyd wasn't expecting to get a senior call-up and he's been able to hold his spot.
"You don't expect to have Rhyce Shaw or Daniel Hannebery miss a couple of weeks.
"That's why you have to be in the best possible form you can because those opportunities will no doubt come before the end of the season."
Asked how O'Keefe has been coping with his demotion, Longmire said: "He's a senior, experienced player and he'd like to be playing senior football.
"But his mindset has been sensational for our reserves.
"His leadership and direction in our reserves both on and off the field has been fantastic and he's the first in the rooms after a game with the seniors.
"It's a real credit to him knowing full well he'd much rather be playing seniors than reserves."
The only current Swan older than O'Keefe is Adam Goodes, who will celebrate another milestone in this week's trip to Perth to face West Coast.
The 34-year-old, who has played nine straight senior games following a 10-month layoff with a knee injury, will break Andrew McLeod's games record for an indigenous player against the Eagles.
Goodes will play game No.341, which also draws him level with Chris Grant in 14th place in the sport's history.
"It's just an incredible story what he's been able to do, to get to this point and continually play consistent football for this club," Longmire said of Goodes.
"He works really hard at his game and what he's been able to juggle this year has been a real credit to him.
"To break the indigenous record is an amazing achievement. There's been some magnificent indigenous players play our game."
Longmire also had a light-hearted moment during Monday's press conference.
The coach stated after Saturday's victory over GWS he would find something Lance Franklin had done wrong, having starred once more with five goals.
He did find something in his review – in a moment where Franklin broke free from a stoppage to kick a brilliant goal.
"I did find something," Longmire said. "When he kicked that goal, he probably shouldn't have been at that stoppage.
"I was halfway through asking Henry Playfair our forwards coach what he was doing at that stoppage and I stopped about halfway through.
"Good thing he kicked that goal."
Twitter: @AFL_JD
