As the final hours of a career with 199 games on the clock ticked down, he was prepared to do whatever it took to earn that final game – and a cherished premiership medal.

He had wept tears after missing the 1996 premiership with a knee reconstruction, was overlooked ahead of the 1998 grand final and a year later was hanging on for dear life.

But as he revealed to his astonished teammates, he won that spot on the bench in North Melbourne’s 1999 grand final team through a mix of opportunity, street smarts and sheer brutality.

Coach Denis Pagan knew Longmire’s body was shot and had told club doctor Harry Unglik he couldn’t pick him as the 28-year-old and teenager Cam Mooney butted heads in a series of one-on-one training drills. Only one spot was available at the time.

But as Longmire revealed at the reunion, he was ready for Pagan’s tricks.

As the pair were warming down on the Arden St fence, Pagan threw one last ball into space. Longmire threw his elbow back into Mooney’s solar plexus so hard that “I just heard him cave in.”

He won that football as Mooney crumpled, with Unglik proclaiming to Pagan that his speed was undiminished.

Longmire’s 200th — and final — game came in a premiership side a few days later, coming off the bench as a back-up ruckman as Mooney ended up playing too at the expense of midfielder Robert Scott.

Two days later, with a medal in his possession, he told Pagan his career was over.

Twenty-five years on, Longmire, now 53, will front up to the MCG already as a premiership player and coach, but desperately seeking another.

And yet across his 36 seasons in elite football, every achievement – bar those early seasons when he was kicking goals for fun – has been hard won.

At times, he has been football’s heartbreak kid.

He entered the final game of the 1990 season with 96 goals under his belt and kicked 2.8, admitting the pressure of the 100-goal barrier got to him.

His career was littered with pitfalls and setbacks: in 1996 he was ashen-faced on the siren in the North Melbourne coaches’ box, then wept in the rooms as the reality of missing that flag hit home.

And as a Sydney coach that premiership success in his second season (2012) has been followed by a trio of grand final defeats of increasingly agonising nature, culminating in a 2022 collapse to the Cats.

Success against Brisbane on Saturday would put him on a par with the likes of two-flag coaches Pagan, Chris Scott, Malcolm Blight and Mark Thompson.

Defeat would mean a 1-4 grand final record, which would be almost like an albatross around his neck.

Those experiences, as a player and a coach, have all shaped Longmire into the person and coach he is today.

BATTLE OF BRITAIN

Longmire grew up on his parents’ 920-hectare farm ‘Sunny Hill’ at Balldale, near Corowa.

But his first game for North Melbourne came as a baptism of fire – as a 16-year-old – in a post-season exhibition game in London against Carlton in 1987, which would become infamous as the ‘Battle of Britain’.

As Pagan said this week: “I was John Kennedy’s runner (in the ‘Battle of Britain’) when I was the under 19s coach. The club had brought John over for his first game and it was the day that Alastair Clarkson clocked Ian Aitken. It was on for young and old. It was like nothing I had ever seen before.

“After the game I was the chaperone for Alastair. We would get into a lift and (Carlton hardman) David Rhys-Jones would be there. It never stopped.

“To think all of these years later, where John has gone and where Alastair has gone. I never envisaged John would want to be a coach.”

100-GOAL CHOKE

As a 19-year-old in 1990, Longmire won the Coleman Medal.

He booted 12 goals in round two and 14 goals in round 14 – the only two games his dad Fred missed that season.

By the final round showdown with Collingwood, he was on the brink of joining Doug Wade and Malcolm Blight in North Melbourne’s 100-goal club.

But in the game at Waverley against Collingwood, the pressure got to him. Needing four goals to reach 100, he kicked an agonising 2.8.

In the rooms after the game, he said: “I tried not to be conscious of it (100 goals), but you can’t help but worry about it.”

Pagan was still three years off getting the Kangaroos’ senior coaching role, but recalled: “It was heartbreaking for Johnny … He couldn’t kick one straight. They (his teammates) were kicking the ball backwards to him in the end.”

IN TEARS

The AFL’s 1996 Centenary season was over before it even started for Longmire, but no one knew what it would ultimately cost him until six months later.

He had kicked 98, 91, 64, 75, 78 and 58 goals from 1990-1995 before it all came to a crashing halt in a pre-season practice match at the Gabba against Brisbane Bears in 1996.

“I’m a bit worried. I am not looking forward to this,” a crestfallen Longmire said at the time.

Pagan figured it might be a good idea to keep him involved with an opposition analysis role in the coaches’ box – the first step on a path to where he is today.

That pain was elevated as the young Kangaroos graduated into a premiership team.

Longmire had to watch on from the coaches box as his great mates won the ‘96 flag.

“We finally got through to a grand final and he missed out because of a knee injury,” Pagan recounted.

Longmire and Liam Pickering had become best mates when they arrived at Arden St at the same time.

But by 1996, Pickering was playing at Geelong, though he made sure he spoke to Longmire on grand final day to check on his welfare.

“He had been a critical part of North Melbourne for a number of years,” Pickering said.

“To miss the club’s first premiership in almost 20 years really hurt him.”

Longmire was the heartbreak story of 1996, which impacted on his teammates, including David King.

“He was just a huge presence in the group,” King said. “To see him on the sidelines through that period was heartbreaking for us.”

The man himself was in tears in the rooms, happy for his mates, but visibly devastated.

He would recall: “It’s not something I dwell on, but you don’t have to be Einstein to work out how tough it is to cop watching a grand final.”

The Kangaroos crashed out of the finals in a preliminary final in 1997, then Longmire was overlooked when the club made the 1998 grand final.

While North Melbourne kicked themselves out of the game in the first half against Adelaide in 1998, he was beginning to wonder if that elusive flag was beyond him.

PARTY LIKE IT’S 1999

Fate seemed against Longmire again in 1999.

He missed a chunk of the year with a hamstring injury, then an elbow issue sidelined him late in the season.

In a year in which he failed to kick a goal in a season for the only time of his career, he became a combative back-up ruckman, coming off the bench to provide support for Corey McKernan and Matthew Capuano.

Sentiment often loses its lustre in the cutthroat month of September, but McKernan this week suggested the players desperately wanted him to play.

“He couldn’t play like he could when he won the Coleman Medal, but what made ‘99 a little more special was the fact it was hard to imagine not winning a flag with John Longmire and what he has contributed to North Melbourne,” McKernan said.

Longmire was recalled for the preliminary final but wasn’t a lock for the grand final, until his educated elbow at the last training session locked him in.

McKernan recalls it well, having had his own experience of the “nasty competitive streak” Longmire was capable of when it meant the difference between winning and losing.

He recounted how when he first came to Arden St, he was pitted in a boxing ring with Longmire.

McKernan joked: “I was this skinny kid from Westmeadows, but I had a long reach, so I went whack and hit him right on the chin. ‘Horse’ got the big lip going and he kicked me … “

“It’s an ongoing joke between me and ‘Horse’, whether from a playing point of view or a coaching perspective, he has that hidden nastiness in him that you need to win.”

He was selected on the bench in the grand final and didn’t come on until the second half.

“I still laugh about it with him,” Pickering said. “He came off the bench and ran on like ‘Crackers’ Keenan (North Melbourne’s 1977 premiership ruckman).

“At the first bounce, he got the biggest corkie you have ever seen and could hardly walk.”

But Longmire pushed through the pain, and even though he had only three disposals, it was a role that McKernan said was crucial.

“As ‘Horse’ will tell you, he went in as a battering ram,” McKernan said. “He didn’t care if he could jump or not jump, he was going to do what he could to be a part of it and play in a premiership for North Melbourne.

“Capuano started like a house on fire and hurt himself and Wayne Carey and Stephen Silvagni were nullifying each other.

“I was the one who got off the chain, so ‘Horse’ playing ruck (meant) I could play up forward and do what I was doing. It enabled us to win the game.”

In the rooms afterwards, with a medal dangling around his neck and a beer in his hand, Longmire expressed relief: “I feel privileged. I can now say ‘I’ve won one’.”

Pagan still remembers his smile that day.

“Just the look on his face … gee, it is imprinted on my mind. He got a game in 1999 and I reckon he must have only just waited until (my) office opened on Monday to tell me he was retiring.”

A new challenge loomed.

SLIDING DOORS

Longmire was in his second year with IMG as a player manager, endeavouring to put together a client list for the 2001 super draft when his phone rang.

It was Sydney coach Rodney Eade. He wanted him to join the Swans coaching panel.

As Pickering, who was then coach of the Western Jets, recalled: “I remember he rang me and said: ‘I’ve got this opportunity to be an assistant coach at Sydney’ and I said ‘Is it something you want to do?’ He said ‘I will give it a go’.”

“Three weeks later, I got a call from him saying that Chris Giannopolous (then with IMG) wanted to speak to me. I asked him what it was about, and he said: ‘I think it is about my job’. I said: ‘I don’t want to be a manager, I want to be a coach’.”

More than two decades on, Longmire has been with Sydney ever since and has been the club’s senior coach since 2011.

Pickering is not only his closest footy mate, he has also been his manager through the highs and lows of his coaching tenure.

Pagan never thought Longmire would be a coach, but King always had an inkling.

Longmire was always “ahead of the curve … always at the front of the pack with everything”, according to King, who recalled he was the first footballer he knew with a mobile phone.

“He was never going to die wondering about anything in life. We all admired his intellect … the question was: could he get it across to 40 blokes?”

The answer to that came almost immediately.

In Longmire’s second season as senior coach, he led the Swans to the 2012 premiership, a swift rise to the top.

If his playing career preached patience in chasing success, his coaching tenure spelled out that things could happen quickly … but a follow-up flag has been more challenging.

THREE GF LOSSES

As Longmire chases a second flag as coach on Saturday, the pain of a trifecta of grand final losses won’t be far from his mind.

There was the 2014 flogging from Hawthorn; the 2016 arm-wrestle that went the Western Bulldogs’ way; and the thrashing from Geelong two years ago that hurt him the most.

Pickering said of the loss two years ago: “I think that one did hurt the most … my personal view is that the Cats were ready (in 2022) and the Swans got there a year early.”

“They were a young team. Yes, they had Buddy (Franklin), but an older Buddy. They had a lot of kids. This time around (against Brisbane) I think they are in much better shape.

“He’s such a good coach. His players love him.”

Sydney chairman Andrew Pridham has watched with admiration the way Longmire has continued to evolve as a coach.

“He knows all he can do is focus on the future, he can’t do anything about the past,” Pridham said.

“He is very aware of the future, very focused on it, someone who understands you have to live in the moment.”

That moment will come at 2.30pm on Saturday and his legacy as a coach might rest on the outcome as footy’s ultimate competitor treks towards the AFL summit again.