Regrets? Denis Pagan’s had a few. He didn’t hold back when asked whether he harboured any about his time at Carlton: “Yeah, going there.”

Pagan was one of nine men who have sat on the iron throne as Carlton coach since 2000, counting 2015 caretaker John Barker.

The dual premiership coach called his stint at the fallen Blues “an absolute nightmare” due to their divisions and disrepair. Pagan’s experience was not isolated. Thirty years on from Carlton’s most recent premiership, Mick Malthouse and David Teague also revealed to this masthead the forces they say led to their sackings.

Pagan joined a club in severe strife, after the Draconian punishments the AFL imposed on Carlton in November 2002 for salary cap cheating during the reign of president John Elliott – penalties the club leadership felt was a case of the AFL hierarchy getting even with Elliott.

The Carlton that Pagan found in 2003 wasn’t what he expected. “That’s an understatement.”

“In retrospect, I probably just should have sat tight,” said Pagan of his decision to leave North Melbourne and sign with Carlton. “I probably would have been better off having a spell, maybe done a year in the media and then seen what was around then.”

For Malthouse, another decorated coach who took the devil’s candy at Carlton, the die was cast in his second season (2014) when his allies, Stephen Kernahan (president and former captain) and Greg Swann (chief executive), left the building together, the CEO having a strong relationship with Malthouse from Collingwood days.

“Let’s start preparing for winter holidays,” Malthouse told his wife Nanette once he learned Kernahan had stepped down, with Swann forced out. Carlton, he said, hated three clubs: “Collingwood, Richmond and Essendon.

“I played for Richmond, coached Collingwood … drove through Essendon to get to Tullamarine to fly out of the joint. So, I mean, that was bingo … I could sense it straight away soon, as soon as Stephen Kernahan left, that was the end of the ballgame.”

Teague was not feted like Pagan and Malthouse. He was the coach with no name, an unheralded caretaker, who raised Carlton hopes and landed the job in 2019 after Brendon Bolton was cast aside.

But his term was even shorter than Malthouse’s – two and a half seasons, a slide, then the sack in the tumultuous aftermath of season 2021.

As with Malthouse, Teague points to regime change – the ascension to power of ex-PwC boss Luke Sayers, who took the presidency from the low-key Mark LoGiudice – as the catalyst for his demise. Teague was ousted when LoGiudice and chief executive Cain Liddle left.

“I felt I had the support of most of the board. But then when the president changed, he [Sayers] wanted – he wanted change, and it was him and probably a couple of others.”

Of the nine coaches who have sat in the hot seat since 2000, six were sacked and paid out – Carlton’s version of honouring coaches’ contracts. Three – Pagan (2007), Malthouse (2015) and Bolton (2019) – were shoved mid-season. Brett Ratten was informed he was finished after a loss to Gold Coast in the penultimate game of 2012.

Only coaching legend David Parkin and incumbent Michael Voss have been spared the blade, Parkin having genuinely stepped down and handed over to Wayne Brittain, who lasted just two seasons.

In that period, Geelong have employed two senior coaches, Mark Thompson and Chris Scott. The Cats have played in an astonishing 14 preliminary finals over 21 seasons, winning four flags. They have not sacked a senior coach since 1988 (John Devine).

Three of six sacked coaches – Pagan, Malthouse, Teague – were willing to talk openly about their experiences at Carlton. Parkin, 81, also provided his take, having mentored Ratten.

Implicitly, the coaching carnage poses questions: Did the Blues fail coaches, or were those coaches the wrong fit? Recruiting failures? What role, if any, did money men – the billionaires and business tycoons in the boardroom and background – play?

Pagan said of the influence of the wealthy, such as billionaire president Richard Pratt, during his period (2003-2007): “There was too many, you know, heavy hitters having their say, who I wouldn’t have thought would have known a football from an Easter egg.”

Several Carlton people pointed to impatience as a fatal flaw. Others cite the saviour complex – the irrational hope that Pagan, Malthouse, Chris Judd, Pratt, Ratten, Stephen Silvagni or even Teague would be their messiah.

Ex-staffers, past board members, former players, assistant coaches and club bosses also offered perspectives on how Carlton turned from the power club into one that won wooden spoons (five) rather than finals.

Today, Carlton’s 30-year premiership drought is second only to St Kilda among clubs that joined the competition before 1995.

The sacked half dozen coaches can be likened to the six wives of Henry VIII, each of them dispatched in different circumstances, yet with the same reality underpinning their demise: failure to deliver what the Crown craved.

In recounting their professional challenges at Royal Parade, the coaches were nonetheless bullish about the 2025 Carlton and what the current group, led by champion Patrick Cripps, could achieve.

“They’ve certainly got some talent on their list now … wouldn’t anyone love to coach that team,” said Pagan.

“There’s not much that they lack,” said Malthouse of the 2025 Blues.

Carlton’s fan base, meanwhile, has proven durable, even if a chunk went into recess for years. The Blues of 2023-24 reminded the AFL of their drawing power, and how this storied, larger-than-life creature, Carlton, can make Melbourne shake.

David Teague

As the last senior coach to be terminated, Teague coached most present players, and has the distinction of having played under Pagan (he won Carlton’s 2004 best and fairest). He served as assistant coach for both Ratten and then Bolton.

Teague reckoned the Blues were on the right path when he was sacked, noting the injuries of 2021, the worst of which was superstar forward Charlie Curnow (knee), who barely played in Teague’s tenure.

“I felt like I had support of the CEO at the time. Other than our injury list, I felt like I was on the right track. So I walk away really comfortable with what I was doing.

“Did I make mistakes along the way? Absolutely. But it’s part of the journey. Am I better coach for what I went through? I think I’m a better coach now than I was.” Teague, who worked at Richmond from 2022-24 as an assistant, is managing Melbourne Grammar’s football program.

“Unfortunately, when … the president changed, I think that my support probably ended up there and Sayers made a decision to move me on.”

Carlton insiders from Teague’s time pointed to his handling of “big dogs” on the playing list as problematic.

Specifically, Teague was easing Marc Murphy, the former skipper, out of the team as Murphy neared 300 games, and did not cuddle the ex-skipper, or co-skippers Patrick Cripps and Sam Docherty.

It is a criticism that Teague accepts has some merit.

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“Managing the transition from that environment and managing those superstars is probably an area that I could have done better.

“Having said that, like Charlie Curnow, Harry McKay, Jacob Weitering and Sam Walsh, I had, I had absolutely, I had that next group of guys that were going to play in the flag. I absolutely had those superstars.

“It was only a couple … Marc Murphy was probably the influential one, but maybe Patrick [Cripps], Patrick, Sam Docherty … were probably the ones I could have managed better.”

As an ex-player and assistant coach at Carlton (and an assistant at West Coast, St Kilda and Adelaide), Teague felt that the Blues had an entitled culture that needed to be eradicated.

“I probably went a little bit hard trying to get rid of this entitled feel. And wanted to make it a country club where people cared about each other and the role player was as important as a superstar, and I probably went a little bit hard.”

Teague said an analyst’s report rated Carlton’s chances of playing finals at eight per cent, due to the injuries, in 2021.

“I never used injuries as an excuse. If I had my time again, I would have definitely brought that up to the board a lot more.”

The review that preceded his removal, overseen by Sayers, also saw the end of CEO Liddle and his replacement with Brian Cook. Teague thinks the review derailed Carlton’s season.

“My understanding is the review didn’t [come] back saying that they had to change [the coach] … it wasn’t, ‘you have to sack him’, it was if you keep [him] you need to put this and this in.”

A source familiar with the review’s contents, speaking about a confidential report, confirmed that the review had not explicitly stated that Teague should go, but that the findings were not positive for him.

Teague was paid out six months’ salary for his coaching deal, a modest payout compared to others.

Denis Pagan

Pagan walked into a Carlton that was on the bottom, over the salary cap, burdened with massive contracts, an ageing list and no draft capital. Players were asked to take pay cuts.

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Worse, due to the AFL penalties and upheaval, Carlton was a house divided against itself.

Pagan and his lieutenants were left holding the bag.

“We all paid a price,” he said. “I’m sure there were so many people’s jobs affected. I’m thinking about assistant coaches and players, how it manifested through all the ranks. The division at the current football club in that time, just amazing.

“You know, splinters everywhere… Board level, administration level. Playing group was split. It was just … an absolute nightmare.”

One insider from Pagan’s time summed up the situation: “Pagan was handed a shit show”.

The Blues narrowly averted the spoon in 2003, won it in 2005 and 2006, netting Murphy and Bryce Gibbs.

But Pagan did not really harvest the benefits of bottoming out, nor the dollars injected via the late Pratt (2007-08) and improved stability under experienced CEO Swann. He was sacked a few months before the Blues landed Judd from West Coast.

“I think Ian Collins, I’ll never forget this statement. He said, ‘we should have handed the keys in’. [Pokies magnate and board member Bruce Mathieson was the first to suggest the Blues should hand keys to the AFL].

“When you go to work there, it just felt like every morning you’d go in, there’d be a bloke standing behind the door with a sledgehammer. They’d hit you in the face and say, ‘how do you like that one? See you tomorrow morning?’ You know, there weren’t many things you could have done to rectify it.”

Pagan’s principal problem – scant top-end talent – was reflected in two major list management calls.

First was the retention of troublesome spearhead Brendan Fevola, whom Brittain had intended to trade.

“We stuck with Brendan because he was the only player on the club [list], who had elite, A-grade talent.”

Second was the large herd of recycled fringe players that Pagan imported to make the Blues competitive. Teague, Digby Morrell and – less successfully – veteran Mick Martyn were castaways from North Melbourne alone.

Pagan said the draft statistics suggested four or five kids taken with very late picks would not make an impact.

“If they were any good, they would have been picked earlier. And we had to try and get a few through the door that could play and hold them together.”

Pagan’s nadir was 2006, when VFL coach Barry Mitchell was encouraged to pitch for Pagan’s job, resulting in Pagan and Mitchell – a former Carlton, Sydney and Collingwood player with friendships among the 1995 Carlton crew – working on different sides of the building.

Pagan presented for his own position in 2006 at a board meeting that was attended by ex-Carlton premiership skipper and AFL commissioner Mike Fitzpatrick, whom the league had dispatched to observe the troubled club.

“That was just so messy. I still haven’t got to the bottom of it, either,” Pagan said of the Mitchell affair, during Graham Smorgon’s brief presidency.

“I can remember saying to Stephen Kernahan, you either support me or sack me.”

Pagan’s clout had waned to the point that the board overruled him recruiting West Coast ruck Michael Gardiner, whose off-field resume did not deter St Kilda, and Richmond’s Ty Zantuck. “I was overruled on Michael Gardiner. I’d spoken to his parents.”

Pagan shared a kinship with Malthouse, as premiership coaches who came unstuck at Carlton.

“How could anyone say that Mick couldn’t coach? What’s he coached – 700 games? He’s got … a first-class record. And it was, was more than coaching that caused the issues.”

Mick Malthouse

Carlton’s board was seduced by the possibility of Collingwood’s 2010 premiership coach extracting an ounce that might deliver a premiership. Ratten’s record – three finals appearances, then an 11-11 season – would gain credence subsequently and assisted him securing a second coming at St Kilda.

Ratten used 41 players in his final season, but his protestations to the board did not save him. He declined to comment for this piece.

The widespread sentiment from Ratten’s club colleagues is that he was stiff to be sacked, and that his weaknesses – problematic relationships with staff such as conditioning chief Justin Cordy and a tendency to micromanage – were due to relative inexperience. Some board members and insiders still defend his removal, which the affable Kernahan found wrenching.

The Blues were blessed to make the finals in 2013 on the back of Essendon’s removal from finals (due to the ASADA saga), turning a ninth placing into a rousing comeback elimination final victory over Richmond, in which Judd and Eddie Betts turned the tide.

The next year Betts was in Adelaide, while a few months later Adelaide CEO Steven Trigg replaced Swann.

“Steven Trigg, he made his mind up pretty early, early days, when he said to me, on arriving, ‘who’ll take your place if you get run over by truck?’ That’s not the sort of question I’d be asking a coach who’d be going into a new season,” Malthouse said.

“I knew I wasn’t going to last there, but I enjoyed the player group, staff were fantastic. Supporters – they have every right to boo and they booed me quite frequently, apparently, according to my wife.

“The only regret I have is something that was out of my hands, is the fact that I was cut at round eight (2015). I would have liked another couple of seasons just to massage the group, add on – and we needed to add on a lot of players.”

Carlton people did not embrace Malthouse, in part because had replaced one of their own and had come from the enemy, Collingwood, who had forced him out.

Carlton insiders point to recruiting mishaps. Murphy and Gibbs were good players, albeit not Scott Pendlebury and Joel Selwood, but Jordan Russell (2004), Chris Yarran (2008), Kane Lucas (2009), Matthew Watson (2010), Josh Bootsma (2011) and Troy Menzel (2012) were an inadequate set of first-rounders.

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Lionhearted ruck Matthew Kreuzer, No.1 in 2007, was often injured and delivered less than Trent Cotchin (pick two); Carlton’s best selection – up to the inspired choice of Cripps (2013) – was Josh Kennedy (2004), who was sacrificed for Judd, needed as a source of revival for the whole club.

Malthouse and the Blues were misaligned from 2014. He had not known of their five-year plan. “I took over, and it was probably two years into it and they said ‘within five years win a premiership’.

“I said, ‘I’ve got news for you, we’re a long way from that. This is going to take a slow burn to get right and it’s going to take patience and it’s also, we’ve got to do it properly … so therefore, we’re going to draft our way out of it’.

“But when you’ve got a board who are stacked with people who are very successful business people, they don’t understand that.”

Malthouse explained the difference between Collingwood and Carlton thus: “Eddie McGuire did not have a rear vision mirror. He never spoke about the past.”

At Carlton, “everything was in the past”.

Malthouse felt the board was too large (13) and often seemed more concerned with their business dealings. “I was staggered there was more transactions being done there between businesses, the football became a secondary sort of thing … You could tell it was more about how their companies were going than how Carlton was going.”

At Carlton then, and for a long time, the companies you keep mattered.

Come back on Tuesday for part two of the series, looking at the powerbrokers and oligarchs who have been pulling the strings behind the scenes.