Exclusive:Dundee boss Steven Pressley lifts lid on £1 fines, nearly quitting and deciding not to sign his son
Dens Park boss outlines his leadership approach and why ‘good values’ are important
When Steven Pressley sends a text suggesting a time and day to meet, it prompts a double take. The suggested arrangement of 10am on Thursday seemed unusual. Two days before a derby, is there not something the Dundee manager ought to be getting on with?
Heaven forfend The Scotsman keeps Pressley from devising the devastating tactical strategy to overcome Dundee United in this weekend’s sole top-flight game. It turns out blockhead football writers are behind the curve, so no surprise there. Matchday minus two, the modern term for two days before a match, is now commonly set aside for rest on Planet Football.
“It allows us to train harder on Monday, Tuesday, Wednesday,” Pressley explains. “In a group where we think development is key it allows us more time, more opportunity on the grass. Often when you train Monday, Tuesday, off Wednesday as used to be the norm, and then train Thursday and Friday you are concerned on a Thursday about your player load, so you are not pushing too hard. While if you train on a Wednesday you can push the players harder. It allows us to train more aggressively.”


It is not necessarily something he learned at Brentford, although it’s natural to reach this conclusion. So much of his footballing philosophy was shaped under Thomas Frank, including how to treat players.
“When I first went to Brentford, the first season in the Premier League we went through a difficult period,” he recalls. “Thomas Frank was very calm, he didn’t raise his voice. He was very thoughtful. Some of the senior players spoke to me, they told me he needs to say a few things and get in about some people. Eventually they navigated their way through it and came out the other end with results, with calmness and most importantly, with no casualties. He hadn’t fallen out with anyone in the squad. He had remained strong in his own way - calm and assured and with real belief in what he is doing. Really smart management, I thought to myself.”
Pressley’s own managerial mettle has been tested by a challenging week. While disappointing, last Saturday's 3-0 Premier Sports Cup defeat against Aberdeen was mitigated by player metrics that exceeded those from the previous weekend’s dismantling of the same side in a league meeting.
There were also extenuating circumstances. A serious knee injury to skipper and talisman Simon Murray, now confirmed to be a dreaded ACL, was a crushing blow that infected the entire afternoon. It was 0-0 when the striker crumpled in an ominous heap on the Pittodrie turf. “There’s been a lot of tears, a lot of emotion,” says Pressley.
“The one thing I would say, if I had to pick one to come back from something like this, it would be Simon.”
The news has cast a pall over Dundee, the city as well as the club. It’s notable the number of Dundee United fans who have sent good wishes to a player who once gave everything for them in a tangerine jersey.
Pressley had his eye on Murray when it happened and immediately feared the worst. “Because we had been working on a few set moves, I was looking at Simon’s position even though he wasn’t on the ball at the time,” he says. “As soon as he went down, I knew it. I knew it…”
All eyes on the Dundee derby
All eyes will be on Tannadice on Saturday evening as the two old rivals tussle in a teatime clash that is being beamed all around the UK in a prime-time spot. You can keep yer – checks fixture list – Brentford v Tottenham Hotspur. Dundee United v Dundee – “Britain’s best derby!” according to a sign spotted outside one Tenerife bar this week – is equipped to fight the lone battle against Premier League heavyweights on the opening weekend of the EPL season.
A veteran of all three big city derbies in Scotland, Pressley can’t wait. “There’s a real opportunity to gain some early momentum,” he says. Pressley's big match preparation has included unloading boxes and reading electricity meters.
Nothing screams ‘improved job security prospects’ more loudly than letting your wife of 26 years know that it’s finally safe to join you in the locale.
June Pressley has left their longtime base in Leamington Spa to move into a house they had already purchased, expecting to spend their retirement years in Edinburgh. A new, improved contract with Dundee was good news for Pressley and Dundee supporters, and bad news for the sitting tenants. They were given notice to leave.
Mrs Pressley has now joined her husband back in their homeland. This week the couple spent their first night in a permanent house in Scotland since 2013, when Pressley left Falkirk to take charge of Coventry City. They were living in Cramond at the time.


Now it’s Edinburgh’s west end, which is still the right side of town for trips to and from Dundee. Daughter Amy, who is 19, has remained in Warwickshire. Given the news about Murray, one wonders whether Pressley considered making it three-quarters of a happy family in Scotland by signing his son Aaron for Dundee.
The Dens Park side have just unveiled Bobby Wales, secured on loan from Swansea, but remain in dire need of striker reinforcements, with Ashley Hay also currently sidelined. Pressley junior, 24, is currently with Walsall, where he is enjoying a fine start to the season – two goals in two games, including one in last week’s impressive 3-0 League Two opening win at Gillingham.
“I did actually think about it,” he says. “I think he is a player who is different and could advance us. I am just not sure about the idea of father-son at the same club. There can always be a feeling from other players that there is a bias towards him, and I don’t want to create that type of environment where people doubt my intentions.
"We spoke about it," he admits. "I have said that to him. He feels the same. I would love to work with my son, he’d like to work with his dad of course. We just don’t think it’s right. It may have been OK for Sir Alex Ferguson…
“Gordon (Strachan) also spoke to me a few times about it,” he adds. “I am so close to my son. Football is not important enough to come between us. I would never want it to come between us and Gordon has said that when he had his sons (Gavin and Craig), it was difficult.”
To quote Arthur Miller, they are all his sons at Dundee. “It’s just my way,” Pressley says. “Ultimately there is a father out there and I am speaking to his boy. My job is to treat their son like they would expect him to be treated.”
£1 fines for bad language
Such treatment is an attractive selling point for Dundee. Long standing issues over moving to a new stadium and training ground challenges – Pressley has spoken many times about the irrigation problems bedevilling them at their current moisture-starved Gardyne College campus base – might count against the club when securing new players. But in Pressley – and technical director Strachan - they have two personalities who, though very different, draw recruits in. Other offbeat methods might also appeal.
Is there another club in the UK where swearing is outlawed amongst the coaching staff? “Staff pay a pound fine if bad language is used,” explains Pressley. Such standards are not driven by him alone. “(Coach) Scott Paterson – he calls himself ‘The Culture King'! – makes sure the policy is followed. I wouldn’t care if anyone described it as ‘soft’.”
Why should he? It’s not as if Pressley has anything to prove. He attended some of the toughest schools, including Rangers in the early to mid-1990s, and survived. “The Rangers dressing room was a strong, strong dressing room when I was coming through,” he says. “Real personalities. You had your Durrants, your McCoists, your Goughs, your Hateleys, your Big Duncs. So many. John Brown… Strong, aggressive personalities.
“It was a great dressing room for standards,” he notes. He himself became a leader at some big clubs and was central to the ‘Riccarton Three’ revolt at Hearts, challenging the authority of bizarro owner Vladimir Romanov. Pressley’s earned his stripes. He’s got nothing left to prove, hence the value placed on personal development and not caring what people think providing you are being true to yourself.
“It’s a safe environment,” he explains, with reference to what he’s creating at Dundee. “It’s an environment where you will find good values. And I don’t think you need to use bad language. I really mean this.”
Not everyone finds it easy. Technical manager David Longwell is trying his best. “He’s completely cut it out," says Pressley. "We joke that whenever he gets into his car at the end of the day he lets out a burst of expletives!” Is Strachan forced to operate with such strictures? “No,” Pressley smiles. “I know my place.”


‘I was close to quitting that day’
If it weren’t for Strachan, someone he considers a mentor, he wouldn’t be at Dundee at all. “When I was growing up I was an Aberdeen supporter and in my early years I was a right winger,” he says. “And Gordon was my boyhood hero. There is a bit of that still when I am around him.”
Pressley recalls crises of confidence in the first half of last season, when he had to be talked out of quitting. He reels off a couple of such occasions – 4-0 scuddings at Tynecastle and Pittodrie.
“I remember after the game (v Aberdeen) I was travelling back to Dundee on the team bus, and then I travelled back to my mother’s (in Dalgety Bay) on the train," he says. "I was speaking to one of my closest friends while on the train. He was pretty honest with me. He said: ‘Steven – you need to get a bit of your old self back’.
“But my old self was not particularly brave, truth be told. Sometimes I pretended to be brave. But I was de-conditioned to the stresses of management having been out for four-and-a-half, five years. It took me a while to get more conditioned to it. I was close (to quitting) that day. I was close after we lost to Hearts….”
Now he hears his name sung at each game. Dundee fans have grown to love their quirky, bookish manager. Although he stops short of over-emoting in front of them, he respects them back. Pressley has spoken about his “authentic” relationship with these supporters, who are among the most loyal and hard-bitten in the land. There’s no bullshit. They won’t mind him talking about the Scotland job, with which he was linked by some people before the SFA plumped for a different SP – Sebastien Pocognoli.
“If the journey was right and the opportunity came at the right time…. most managers would love to manage their national team,” he says. “I don’t have any clear pathway ahead of me. I just manage day to day. Like a lot of things in football, it’s about timing isn’t it? I still have a lot of work to do with Dundee first.”
He is relishing feeling settled again. “I had a great year staying with my mother. She is now 79, to have a lot of time with her has been amazing. But this gives me a little more stability round my family, with my wife being up now. I love Edinburgh, because I can escape football…it is a cosmopolitan city, with some areas where I can escape.” As a former Hearts skipper, being able to roam unharassed is important. “I do get noticed but I find I can get away from it,” he says.
Thursdays, when he’s not drinking coffee with journalists eager to hear his views, are ‘thinking days’. He likes to walk around Edinburgh with a canvas bag slung over his shoulder, just another flaneur in a city currently full of them.
He empties his head of tactics and instead figures out how to break it to players that they won’t be starting at the weekend. “I think more about the difficult conversations that I sometimes have on a Friday…. how can I deliver them empathetically and honestly?” he says. “Because you should not go into these conversations without thinking a lot about the person.”
No wonder these players, even frustrated ones, regularly speak about loving playing for Pressley. He’ll lead his squad across Tannadice Street on foot on Saturday afternoon, as per tradition for the visiting team. Whatever else unfolds in Britain’s best derby, he can feel confident about one thing: these players all have his back.
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