IN THE winter months of 2009, before Sydney had conjured any thought of a coaching succession plan with its premiership mastermind Paul Roos, the club's senior assistant John Longmire was being heavily courted by North Melbourne to be its next senior coach. The Swans, naturally, sprang into action to concoct the perfect plan to keep the man known as 'Horse'.

Only it failed.

Longmire, a Kangaroos premiership player in 1999 and an ambitious assistant with designs on stepping into a coaching hot seat in the near future, was understandably intrigued by the prospect of a return to Arden Street. So much so that the Swans' president at the time, Richard Colless, tasked fellow board member Andrew Pridham with a covert mission. Offer him a different job, one that – unlike its coaching position – was vacant at the time.

"We didn't want to lose John, but Paul was the senior coach," Pridham tells AFL.com.au.

"I was given the job to take John out to dinner and have a chat to him. We thought he could have gone more into the administrative side. I said, 'We don't want to lose you. Do you really want to be a senior coach?'"

It was there and then that a proposal was made for Longmire to become Sydney's new general manager of football. It was an opportunity that would give him the chance to run the club's entire football department, but one that would also mean shelving his immediate plans to become a senior coach.

"John is never backwards in coming forwards, and he just said no," Pridham remembers. "He said, 'No, I want to be a senior coach'. Fair enough. We had another glass of wine and that was it."

Just a couple of weeks after that fateful evening, the chat had sparked a remarkable chain of events that, more than a decade on, will result in Longmire coaching his 300th AFL game when Sydney hosts the Western Bulldogs at the SCG on Thursday night.

At a hastily arranged press conference in the days following, Roos announced that he would step down at the end of the following season, Longmire would take the reins from 2011 onwards, Andrew Ireland would move from general manager of football to CEO, and Dean Moore would take on the head of football job once speculatively offered to Longmire.

"I didn't hear about that story again until after we won the 2012 premiership and he raised it with me out on the ground. It was the first thing he said to me," Pridham says, almost 14 years on. "It was pretty obvious that he wanted to coach, and luckily he did."

A knock at the door

SO QUICKLY did the next phase of Longmire's journey happen, he didn't even tell his wife.

Set to board a plane to Victoria after his brief and abrupt dinner with Pridham, where he would meet with senior North Melbourne officials and discuss replacing the recently departed Dani Laidley, he got a knock at the door of his office. It was Roos, informing him that he had tendered his resignation, effective at the end of the next season.

"My wife thought I was heading to Melbourne during that day. Anyway, it's a long story but by the end of that afternoon I'd been offered the job for two years and took it without speaking to my wife," Longmire tells AFL.com.au.

It was the culmination of almost a decade's worth of coaching as an assistant with the Swans, of attending board meetings, list management strategy sessions, and filling in for Roos during the odd press conference. It was also the pay-off for a series of other opportunities, either turned down or missed, like the St Kilda coaching job that went to Ross Lyon in 2006, a senior assistant position at Geelong in 2008, and the now infamous offer of the football operations role at Sydney in 2009.

Longmire had served his time and was ready for his opportunity. Or so he thought. Having worked under Roos for one final season in 2010, the baton was finally passed that September. However, after just one week in the role, a then-39-year-old Longmire was left wondering why he had wanted it at all.

"I thought I was as prepared as anyone for the transition with 'Roosy'. I had a lot of responsibility, I was involved in all of the draft and trade, I was doing that all the way through. I thought I had a great feel for it, but I remember at the end of the first week just sitting there going, 'Gee I have no idea what I'm in for'," Longmire says.

"It was that big of a jump, from an assistant coach to a senior coach. You don't really understand the jump until you've done it. There's a big gap between having a great idea and making a decision. I realised pretty quickly that I can have all of the best ideas in the world, but it's a big jump to then make a decision and being responsible for those decisions."

Premiership players like Leo Barry, Jared Crouch, Nic Fosdike and Michael O'Loughlin had just retired, fellow flag winners such as Brett Kirk, Craig Bolton and Tadgh Kennelly would do likewise in the 12 months after Longmire took the reins, while the introduction of expansion sides Gold Coast and Greater Western Sydney meant that Sydney faced the prospect of conducting its looming rebuild within a compromised draft.

"It struck me then, at the end of that very first week, that it was going to be a bit of a challenge. Coming off that era, the timing of it, it just seemed to be that we weren't quite sure what was in front of us." Longmire says.

But, just 552 days later and amid all the uncertainty, the Swans were premiers once again.

Getting 'blind' at Ravesis

ON THIS occasion, it was a knock at Jarrad McVeigh's door that proved a surprise.

McVeigh, Sydney's loyal and long-serving 325-game star and the club's 2012 premiership captain, had just announced his retirement when the knock came. There, a surprise guest at his house, was Longmire. He'd brought with him a bottle of red wine and an invite to Ravesis, a trendy restaurant in Bondi.

He wasn't the only one to get the invite. When the two arrived later that night, they were met by Adam Goodes, Jude Bolton and Michael O'Loughlin at a table reserved under Longmire's name. Every player to have ever played 300 games for the Swans to that point, sharing dinner – and more than a few drinks – on a special night.

"We all got blind together," McVeigh laughs.

"I was playing that weekend. But to have those guys there, it was a special moment. He does things like that for a lot of people, understanding their journey. It's little things like that that make you go, 'that's pretty cool'. I thought I was just going for a quick beer with him, I didn't know they were coming. It was awesome."

Longmire's version of events is, understandably, quite hazy. But, while drinking during a game week isn't a common occurrence under his stewardship of the Swans, he does remember McVeigh shaking off any hangover in a 45-point win over St Kilda just a few days later.

"I just said to the guys, ''Macca' has announced his retirement … would you blokes be interested in a quick beer?' I said it was my shout, which I probably shouldn't have said, because as quick as lightning the texts came back saying, 'Yep we're in'," Longmire says.

"We sat down and got some photos together and had a few beers. Then we had a few more beers. We just soaked up the whole thing. I was lucky enough to have an involvement in all of their careers. You sit there with some legends of this footy club, having a few beers, and you think, 'This is pretty cool'."

McVeigh's special night is just one example of Longmire's enduring sense of duty, responsibility and loyalty to his players. It's a trait that was passed to him by Roos, who was not only a coaching mentor but someone that handed down countless lessons on life, empathy and leadership to his successor.

Longmire credits Roos for understanding the difference between footballers as players and people. "He was able to be close with them, yet be their coach. He could drive, set standards, challenge them, but also have some fun with them. He had a great balance as a coach," Longmire says.

Longmire himself, though, has taken Roos' approach and made it his own.

"His relationship with the players is as good as I've ever seen," Swans CEO Tom Harley says.

"That speaks to the evolution of coaching. Coaching is ultimately a leadership position around influence. It goes without saying, with influence you've got to have the foundation of a relationship. He invests significantly in that."

Longmire, now 300 games into his Sydney career, is the definition of a modern coach. He glides effortlessly between talking to a 36-year-old Lance Franklin and an 18-year-old Jacob Konstanty. In doing so, he keeps both players – and himself – endlessly motivated.

"He's got great empathy and really good emotional intelligence," club legend Brett Kirk says.

"He understands people. All of the players would say that if something's going on and you need to have a conversation, it's easy to walk through his door and have a yarn. He definitely has empathy for people. While footy is a high priority, he also understands that there's a lot of other stuff going on in guys' life. He gets it."

A curious mind

IT WAS a tactic inspired by Rhyce Shaw, but emblematic of Longmire's approach.

When the Swans lost the 2014 Grand Final, smashed by 63 points at the hands of the Hawks, morale was understandably low. More than a few sides to have been in such a position, both previously and afterwards, have withered in the years that followed a disappointing Grand Final performance. Longmire would not allow that happen.

As he pondered how to approach the defeat with his players, Shaw stepped forward to retell the story of how Collingwood's unsuccessful Grand Final teams opted against watching either of the games back. He gave his own personal view that it didn't help him process a bitterly disappointing loss when he was part of the Pies' side in 2003.

So, Longmire gathered with his players and watched the game back. They responded in the years to come, returning to the finals in 2015 and to the Grand Final in 2016. He has since taken a different approach to every success and setback, gauging the experience, morale and body language of his playing group to devise his response.

"You have an understanding and a solid philosophy, a foundation of who you are and what you are. But, on top of that, you've got to be adaptable and flexible. You've got to be able, in the moment, to work out which way you need to go," Longmire says.

"You don't always get it right. I always talk to our captains about leadership being getting things right seven times out of 10. That means three times, you're going to muck it up. It's just a fact of life and part of the role, understanding that you're going to make many mistakes. I make plenty of them."

For as much as Longmire himself is a mastermind of his profession, perhaps his greatest coaching asset is his ability to step back. Taking on advice, delegating and identifying his own weaknesses have enabled him to adapt and grow stronger.

He is in constant dialogue with his chairman, chief executive, list manager and head of football, while he is just as frequently discussing theories and ideas with his three captains, as well as his entire playing group – taking feedback from Shaw, then a veteran Swans player, was just one example of Longmire looking outward for ideas – to improve the side's overall performance.

His coaching group is therefore in keeping with such a philosophy. As well as McVeigh, who came through the ranks at Sydney, Longmire has fought to poach former rival Dean Cox from a successful West Coast program, Don Pyke from Adelaide following its surge to the 2017 Grand Final, and Ben Mathews from Melbourne's setup under Simon Goodwin.

"He's inquisitive, curious and always looking at different ways to do things," Harley says.

"He's not one to stand still. The cliché is if it ain't broke, fix it anyway. He takes a positive and forward-thinking mindset to everything he does. Every time we bring in new people, we'll ask them what they think as opposed to, 'You're coming in and this is the way you're going to do things'. He can absolutely park his own ego and park his own agenda to the side, take things on board and then shake them up."

The head of the table

THERE is something Brett Kirk thinks is important to understand about Longmire.

"Firstly, he loves his food," Kirk laughs.

It might seem an irrelevant point, but it's not. Longmire is not only Sydney's senior coach, he is also the figurehead of the entire football club. He plays a central role in coaching, yes, but also in list management, the growth of football in New South Wales, pathway systems, Academy setups, AFLW programs, and much more. He even provided a significant influence in the planning for the club's elite new $70 million Moore Park facilities.

Longmire plays down his influence on the club's new state-of-the-art headquarters, but it's understood he delivered invaluable insight during the design process. It's why certain features, such as a family room and the location of the huge dining room, are where they are. Indeed, that influence is reflected on any given afternoon when Longmire is at the head of the table entertaining players and staff during lunch breaks.

"The flow of the athlete when they arrive, coming through the eastern side there, the first space they come into is player wellbeing and welfare. You work your way through development coaches, then you go past assistant coaches and the senior coach before you get to the changerooms. That athlete flow is really important," Harley says.

"From just the overall club feel – and one thing I would say about John is that he's a club coach, he's not just a team coach, he coaches the club – so the connectedness of the whole of club is there, with the dining room as a bit of a campfire. From the senior coach, to the chairman, to the commercial department, to AFLW. Everyone mills there, which is terrific."

That's why Kirk, brought back to Sydney in 2015 and now serving as the club's head of player wellbeing and development, thinks Longmire's love of food is an important thing to understand. It allows him to stay connected with everyone involved in the football club.

"He's generally the first up there," Kirk says of the queue for lunch.

"But he wants to keep his finger on the pulse, so he gets around the boys and knows what they're up to and what's going on in the rest of their life. That's important, as a coach, to understand that. With training and other things going on, it's the time to have a feed and be able to switch off and have a laugh. He does command the table at times."

In terms of what's kept Longmire going – not only will he reach 300 games on Thursday night, but he is also currently the longest-serving coach of a single club in the AFL – it's just that. Every passing day as an AFL coach keeps the 52-year-old motivated. Rather than be wearied by his past experiences, he is excited by the next one.

"One of the reasons he's lasted as long as he has and why he is so important to the club is that he has a broader view, it's not just about winning games on the weekend. Clearly, that's the most important thing and that's what he's paid to do, but he goes out of his way to do a lot of things that people don't see," Pridham says.

"One of the things he's done incredibly well is adapted as times have changed. A lot of coaches probably struggle with that, but he's done that really well. Whatever it is that makes players tick in 2023, particularly with the younger players, is vastly different to what it was in 2002 when he started or in 2011 when he started as a senior coach.

"People have changed. He's been very good at adapting. Because he takes a lot of pastoral care in the players' welfare and their families, he's been able to be highly effective with players. He's remained relevant for them and he's adapted his approach to get the best out of everybody. That's really what has been his secret sauce for us."

Five minutes of bliss

ON THE rare occasion Longmire allows his mind to drift, he thinks back to one moment.

"It was on the bus after we won in 2012. We were going from the changerooms, going around to the function at the tennis centre. It was only a five-minute journey, but I sat there with a beer and thought, 'This is pretty cool'," Longmire says.

Looking back, for him, doesn't happen often. There is too much other stuff to do. Too many selection decisions to make, too many list management holes to ponder, too many premierships to plan for. Asked to reflect on his 300 games as senior coach of the Swans, his answer is a typical one. "To be honest, I don't reflect," he says sternly.

It's why Sydney has been as consistent and as successful as it has been under Longmire's guidance. There is the premiership in 2012, of course, but there have also been the 10 finals qualifications and 24 finals matches during his 12 full years in charge. There have been the six top-four finishes and the four Grand Finals. There is also the remarkable win-rate, which currently hovers at around 62 per cent from his 300 games.

"He's just relentless in his pursuit of wanting to improve himself and the playing group and he just doesn't stop. It's quite extraordinary, he just doesn't have a day off ever. He just continually goes and goes and goes," McVeigh says.

"We talk about being a ruthless footy club. Well, it starts with him. He is. He's just got a relentless pursuit to try and improve the group and win and a great drive to do that. He sets the standard in that for us."

A 200-game player at North Melbourne, there was hardly anything Longmire didn't experience. From winning a Coleman Medal at just 20 years of age, to playing in three preliminary final defeats, to missing the side's 1996 premiership through injury, to finally securing Grand Final glory in his final match in 1999. His journey as a player has shaped the legacy he is leaving as a coach. Only he finds this particular ride far more enjoyable.

"It's much better as a coach, much better," Longmire laughs.

So, what next for the man who has done and seen it all? With a playing group shaped in Longmire's image at his disposal, a brand new facility born from Longmire's ideas recently built, and a football team ready to compete for premierships filtering through Longmire's office door each morning, that's one question 'Horse' can't answer.

"I don't know. I do not know," Longmire says.

"It's got an end point, but I just don't know. It's a bit like looking back, I don't think about it. I'm just trying to get the team better and trying to leave the team, whenever it is that I finish, in a good space. The same goes for the football club in general.

"I'm very fortunate. I'm very lucky, so lucky to have been here for 20-plus years. It doesn't happen too often. I don't take that for granted. It's just a fantastic football club and I'm very grateful for that. I know I've got a job to do here and hopefully I do it well."