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Jimmy Calderwood’s Dunfermline lit up the early years of Scottish football’s new century

Ambitious, Dutch-influenced and unconventional, Dunfermline were probably the best provincial side of the Noughties.

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This article first appeared in Issue 24 which was published in June 2022.

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It’s easy to forget, given how quickly he became one of Scottish football’s most instantly recognisable and talked about figures in the years that followed, but Calderwood was a relative unknown in his homeland upon first arriving at East End Park, having spent his entire playing and management careers in England and the Netherlands up to that point.
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He had his house in Torryburn and never wanted to leave there, he even had part of the old Dunfermline pitch in his back garden, the last grass pitch, before they laid the plastic one. It was great, the best garden in the estate!

Stillie; Nicholson, Skerla, Labonte, Byrne; Young, Mason, Dempsey, Young; Crawford, Brewster.

Ring any bells? I recently carried out a bit of a survey along these lines. It was not conducted under particularly scientific conditions, taking place in a cramped little bookshop/pub on Lisbon’s Pink Street halfway through a stag do, but the results were interesting nonetheless. Yes, said my motley crew of respondents – made up of Celtic, Rangers and Hamilton Accies fans, and even one Rapid Vienna admirer – of course they recognised Jimmy Calderwood’s Dunfermline Athletic side. The swashbuckling style of play, the unstoppable strike partnership, the top-six finishes, the snazzy pinstriped shirt with RAC stamped on the front, the sun-kissed Saturday afternoon at Hampden when the above starting XI was half an hour away from immortality – they remembered it all.

Homer Simpson famously complained that “every time I learn something new, it pushes old stuff out of my brain” but that doesn’t seem to apply to football fans of my generation; still dedicating infinite gigabytes of our random access memory to stuff that happened on Scottish pitches in the late 1990s and early 2000s. Perhaps some of it doesn’t deserve to occupy so much space in our minds, and should have been replaced by Wordle scores and Joe Wicks recipes by now, but the Calderwood Dunfermline team? The one that introduced Dutch Total Football to the West of Fife? The one gallus enough to sometimes go 2-4-4 away from home, even if it meant the occasional 7-1 scudding at Tynecastle? The one that reached the Scottish Cup final, and qualified for Europe and bloodied the nose of both Celtic and Rangers at a time when the Old Firm were as strong as they have been this century? That was a team worth remembering.

The tragic irony, of course, is that the man chiefly responsible for creating those special memories no longer has access to them himself, as he suffers with the early onset Alzheimer’s he was diagnosed with in 2015, when aged just 60. It ended, like so many tales of provincial rebellion in Scottish football, with recrimination, relegation and, eventually, administration, a tailspin that began with the manager’s controversial defection to Aberdeen in 2004 and which some would say the Pars have never fully emerged from. But for those who went along for the ride on an adventure that started back in November of 1999, the Jimmy Calderwood era at East End Park has a worth that appreciates with every passing year.

There’s been a promotion

We begin with the man at the centre of Scottish cultural discourse at the turn of the century: DI Robbie Ross. DI Ross, aka actor John Michie, wasn’t just the guy you called when there’d been a murrdurr back then, he was also, it seems, the go-to guy when you needed a distinguished voiceover on your football club’s end- of-season documentary. Although it’s a safe bet that a few VHS copies are lurking in dark corners of Dunfermline charity shops, Going Up – season 99/2000 is not currently available on eBay or Amazon. But thankfully, someone has uploaded the whole thing to YouTube, where you can enjoy nostalgic glimpses of bygone grounds like Love Street, slow-motion footage of Stevie Crawford’s celebrations soundtracked by a bad Limp Bizkit tribute act’s riffs and record scratches, and a black-and-white sequence building up to the decisive clash against St Mirren so grimly ominous that you assume the match coincided with a nuclear apocalypse.

The star of the show isn’t DI Ross, however, or even top scorer/player of the year Crawford, but the guy with the slick gelled hair and black waistcoat, sat in a soft-lit trophy room as he calmly opines: “I really do think it will be easier for us in the Premier League – no’ being big-headed about it.”

It’s easy to forget, given how quickly he became one of Scottish football’s most instantly recognisable and talked about figures in the years that followed, but Calderwood was a relative unknown in his homeland upon first arriving at East End Park, having spent his entire playing and management careers in England and the Netherlands up to that point.

“Some wido fae Glasgow comes in and they think, What are we getting here?” as the man himself put it years later. The Calderwood we see in the documentary is unrecognisable from the gurning, perma-tanned caricature that was a fixture on Only An Excuse throughout the early 2000s. He is young – just turned 45 – vital, suave and confident. Little wonder, considering he’d led NEC Nijmegen to an impressive eighth-place finish in the Eredivisie not long before. So while concrete info was thin on the ground, this was clearly a man who knew his onions (or should that be tulips?), as radio presenter and Pars fan Steven Mill recalls. “I think we were about six points off the top of the league when we sacked Dick Campbell, but it was obviously because we were bringing in this guy called Jimmy Calderwood… who none of us had even heard of. But it was like, fucking hell, if we’re paying something like 200 grand compensation to NEC Nijmegen, he’s obviously pretty good!”

Mill was 10 at the time of the appointment, the perfect age to fall in love with football and with the team Calderwood’s famous wheeling, dealing talents would construct over the next couple of years. But the effect was far from instant. Dunfermline were favourites for the 1999/00 First Division title having just dropped down from the SPL the season prior, but didn’t half make hard work of it. Under Campbell (and just think how much more bonkers this tale would be if he had remained in charge…) the Pars drew six of their first 12 fixtures, and while things perked up under caretaker manager Jimmy Nicholl and then Calderwood – partly due to the capture of hardened pros Lee Bullen and Ian Ferguson – the momentum drained away again with defeats to Raith Rovers and Livingston early in the new year.

That big nuclear standoff at Love Street in early March ended 2-0 to Dunfermline, putting them a point clear with eight games to go, but further slip-ups meant that St Mirren went on to seal the deal. Yes, you read that right. “Tom Hendrie’s St Mirren” may not roll off the tongue the way “Jimmy Calderwood’s Dunfermline” does, and it’s doubtful my Lisbon stag-do companions could summon any particular memories of that Saints side beyond Mark Yardley’s iconic waistline, but it was them and not the Fifers who won the title by a five-point margin. If this was any other First Division season between 1997 and 2011 Jimmy and co would have been consigned to another year of purgatory. But fate, destiny or just plain old luck intervened.

This was the year that the SPL expanded from 10 teams to 12, and although the initial plan was to have a playoff involving the bottom club (Aberdeen) and the second and third-placed finishers in the First Division, that was scrapped when Brockville once again proved to be an albatross round Falkirk’s neck, therefore Dunfermline’s promotion was secure as soon as they nailed down second place, which they did by winning 2-1 at Inverness on the third last matchday. Crawford and Bullen added their John Hancock to permanent deals, a soon- to-be cult hero by the name of Andrius Skerla arrived from PSV Eindhoven, and Calderwood whisked the squad off to the Netherlands for a little Total Football refresher in pre-season, as the Royal Burgh began to wind up towards its most exciting event since The Singing Kettle roadshow came to town…

Zlatan Brewster

The first thing that strikes you about Scott Calderwood is his accent: an Anglo-Dutch hybrid a million miles away from his father’s broad Castlemilkian. But it soon becomes clear that that’s pretty much the only thing the two don’t have in common. Like his dad, Scott started out at Birmingham City, is fluent in Dutch, has a soft spot for a certain team from Govan and has by his mid-forties already compiled an extensive coaching CV, mostly with the same clubs Jimmy worked for. He was even in the running for the Dunfermline job last year, and at the time of our interview is busy managing one Dutch club (third-tier SV TEC) and coaching at another (second- tier Den Bosch). But 20 years ago, he was a midfielder who regularly joined up with the Dunfermline squad for pre-season training and was left feeling envious of the team spirit he saw blossoming there.

“When I look at my dad’s career, he was always successful when he had a lot of characters in his team,” Scott tells Nutmeg. “It was never a dull moment at Dunfermline. At that time, I played for Heracles Almelo, and our pre-season always started a week later in Holland, so I used to go over and do a week with them because I knew it would be hard work with my dad. I used to always hope he would say, ‘Scott, come here and sign with us,’ but we had already been through that at Willem II, when I was 16 and made my debut in the Eredivisie. It never materialised, but I was like, ‘Just sign me, I want to be part of this group!’”

Dunfermline’s freshman year in the shiny new 12-team SPL wasn’t without its hiccups – that 7-1 chasing at Tynecastle included – but the Pars avoided the drop (unlike Hendrie’s St Mirren) and were even a point away from finishing in the top six before eventually backsliding into ninth place. They would put that right by climbing up to sixth the following season, and by the summer of 2002 the “classic” Calderwood Dunfermline team was almost fully assembled.

Part of Calderwood’s appeal, as a showman as well as a manager, was that he always seemed to have an exotic trialist or rumoured signing up his sleeve all year round, in those final knockings of the old Wild West transfer market before UEFA imposed the summer and winter windows in time for the 2002/03 campaign. His biggest coups tended to be in Fife for a good time and not a long time; like Jack de Gier, the popular Dutch striker who lasted only a couple of months before homesickness got the better of him, or Youssef Rossi, the Moroccan international defender and “absolute nutjob” – as Mill puts it – who by all accounts would have earned a move to a big English club if only he could have resisted his infamous unsanctioned sabbaticals back in Casablanca and taking lumps out his teammates’ shins in training.

But the more impactful signings long-term tended to be found in less eclectic locations, like Barry Nicholson and Gary Mason – youthful fringe players at Rangers and Manchester City respectively – and Craig Brewster, a 35-year-old journeyman striker freshly let go by Hibernian, brought in to “hold the ball up and get on the end of crosses”, as chairman John Yorkston understated it at the time. He would do a hell of a lot more than that over the next 2.5 years.

Every one of them was a hero in the eyes of Mill, who by this point was travelling all over the map with a group of his dad’s mates, getting into away games with complimentary tickets laid on by Calderwood himself (a regular in the same Cairneyhill pub frequented by one of the party) and namedropping Jim Leishman to blag their way into Livingston’s club car park. “It was great, just fannying about and going to matches all over the country,” he laughs. “You’re going home and away expecting to win, which is not something that happens very often to Dunfermline fans, particularly in the top flight. Calderwood was a total breath of fresh air, a relatively young manager coming from Holland with this possession-based style of football. Fans even got frustrated at times because we’d overdo it and try to pass teams to death, but we actually gave him a new deal when we were on a terrible losing run, because it was obvious this guy was going to take us places.

“We had Scott Wilson and Skerla, both really solid at the back; Scott Thomson, a criminally underrated player and total powerhouse who could play anywhere; Nicholson, just a tremendous footballer; Mason, an unsung hero who you really missed when he wasn’t in the side; and, of course, Crawford and Brewster up front, who teams found really difficult to contain, simply because the understanding and partnership between them was like nothing I’ve seen since.”

For most people Brewster was the guy who’d ended his boyhood club Dundee United’s long wait for the Scottish Cup with the winner in the 1994 final, then disappeared off the map. He had returned from five years in the Greek league with grey hair and even less pace than Yardley, but at an age when most pros are more interested in their property portfolio and golf handicap, the new Pars No. 10 suddenly began playing like Joe Jordan spliced with Zlatan Ibrahimovic, producing the best form of his career, and of Crawford’s. The pair’s partnership was – if we can put the Larssons, Suttons, De Boers and Arveladzes to one side for a moment – nonpareil in Scotland during season 2002/03.

Dunfermline were carried to fifth place on a wave of Brewster and Crawford goals, 38 of them in total, with Hearts, Aberdeen and Dundee United all on the wrong end of heavy scorelines and poor old Hibs tanked 4-1 then 3-1 at Easter Road. One thing Jimmy’s boys hadn’t managed yet was a victory over either of the big two. They would scratch that itch the following year, in a season of stunning success not seen in those parts since the 1960s. But the financial rot that eventually brought it all to a sad end had already began eating the club from the inside.

Rush, Reidle, Papin & Les Battersby

“Whenever you went into the town there was a total buzz around it, you could see it in all the pubs. I’d go up to the bank or to pick up something and people would be saying, ‘Scott, can you get me a signed ball, can you get me this, can you get me that.’ Everybody wanted a piece of you, it was great times.”

Scott ‘Nipper’ Thomson was a Bert Paton signing who arrived at the club a year-and-a-half before Jimmy did, but few lived through the Calderwood era quite as intensely as the versatile defender. Having started out as a striker at Aberdeen, he played in literally every position except goalkeeper for Dunfermline, was on the verge of a Scotland call more than once, was made club captain after Ferguson left and also served as cabinet minister for morale; i.e. the one charged with taking 16 or 17 of his teammates paintballing (“You never wanted Youssef to be in the opposing team”) when Calderwood responded to a string of negative results by declaring: “The boys need a day out.”

It’s a mark of how wedded the Aberdonian became to the club and the town that he still lives there and regularly takes his daughter, who plays for Dunfermline Athletic Girls, to games at East End; although looking at the Pars’ results this season it’s unclear what either has done to deserve such punishment. “My relationship with the Gaffer – I still call him that to this day – was always really good, he took an instant shine to me,” Thomson says. “He was very demanding, and that was one of the reasons we got on well – I needed a kick up the backside and he gave me it. He was always really positive. I had never seen this before but at the start of the season he would put up a list of all the teams we were going to be playing and how many points he thought we should be getting against them. Then he would put up another one with all the positions each player was able to play.

“He would put your name everywhere! You would have your points targets against the top sides, but as you got lower down the league he would say things like, ‘I want 10 points from them, at least three wins’. When he first came in and we’d only just been promoted, everybody was going, ‘Is he aff his heid?’ But every year we got to the points total, then he made us go higher. It wasn’t by chance that we finished sixth, fifth, then fourth. It gave you a self-belief. The mindset went from ‘Does he really think we’ll get that?’ to ‘Yeah, we’ll get that, no bother.’”

As captain, Thomson was also the first to get an inkling of the trouble that was on the horizon, on a bus journey back from a snowed-off cup tie at Clyde. “The Gaffer said, ‘We’re training tomorrow’, and I said, ‘The boys are asking what the bonus is?’ And he said, ‘There’s no bonus.’ I laughed, because I thought he was winding me up. But he said, ‘There’s no bonus, there’s guys coming in to talk to you about it tomorrow.’ Then the guys in suits came in on the Sunday and said, ‘You guys need to take wage cuts, and if you don’t, you, you, you and you can leave next week, then it’ll be you, you, you and you the week after.’ The wages were deferred but we never got them back, so your contract is more or less ripped up.”

Quite simply, the sums weren’t adding up for Dunfermline. Despite the outstanding results, the buzz around the town and a string of wacky publicity stunts on matchdays, there just wasn’t enough footfall through the turnstiles to make it all economically viable. “The game immediately after we reached the Scottish Cup final was at home to Motherwell, and the crowd was sub- 5,000,” notes Mill. “It was never really sustainable, we were getting crowds of around 4,000 and budgeting for double that. People always say, ‘Why didn’t you question it?’, and you go, ‘Because we were going and skelping teams! We were going to Easter Road and beating Hibs 4-1!’ It was just wild how good we were. It’s probably a good case study of ‘Why do people not go to the football?’, because in the 1980s and 1990s Dunfermline got crowds of 13/14,000 regularly, but it was £2 to get in then. We went through a period where we would almost have half-time shows. No’ quite the Super Bowl, but stuff like Paul Lawrie coming out after he’d just won The Open, and Les Battersby doing the half-time draw. Then obviously we had the plastic pitch as well, atrocious but the first one in Scotland for many years. They gave former footballers money to say, ‘Oh, this pitch is amazing,’ so we had Ian Rush, Karl-Heinz Riedle and Jean-Pierre Papin taking penalties on the pitch at half-time! Bizarre times at Dunfermline.”

“It was mayhem, but you’ve got to keep playing,” remembers Thomson, and to him and his teammates’ great credit, they did. The Pars beat Dundee United, Clyde, Partick Thistle and Inverness Caley to reach their first Scottish Cup final since 1968 (and qualify for Europe for the first time since ’69 ) and garnered 53 points in the league, the club’s record SPL tally. In December, they recorded their first league win over Rangers for 31 years, Brewster (now 37) and Crawford terrorising the likes of Henning Berg and Paolo Vanoli in a 2-0 victory at East End Park. Then in May, Dunfermline ruined the day of Celtic’s league trophy presentation with a remarkable 2-1 win at Parkhead achieved despite Brewster and Crawford not even being in the squad as a precaution. It was one of just two league losses Martin O’Neill’s champions suffered all season, but they would have the chance for revenge less than three weeks later at Hampden.

“We got to the League Cup final in ’06 and the Scottish Cup final in ’07, but ’04… that’s the one we remember,” Mill reflects. “It felt like a once-in-a-generation thing. 17,000 Dunfermline fans there, a hot day at the end of May – classic Scottish Cup final scenes. Then we score just before the break so we’re absolutely bouncing at half-time and they play ‘Into The Valley’ over the Tannoy. Glorious.”

Henrik Larsson hates Dunfermline

On paper the final should have been a simple Celtic rout. The Hoops had knocked Barcelona out of Europe that season, won the league by a 17-point margin and trounced Dunfermline 4-1 and 5-0 earlier in the campaign. On top of that, it was Henrik Larsson’s last competitive game for Celtic, and the man took an almost perverse pleasure in tormenting the Pars, scoring 28 times against them across the previous seven years. And yet, despite injury depriving them of Thomson and their entire regular back four except Skerla, Calderwood’s men exasperated Celtic in the first half, creating a string of decent chances before taking the lead when Skerla’s moonshot of a header left a 19-year-old David Marshall lying baffled in the back of his own net. Early in the second half a Bobo Balde handball in the box went unpunished, the ball instantly hoofed upfield and bouncing invitingly into the path of Larsson when young stand-in defender Aaron Labonte slipped… “If there was VAR, that definitely would have been a penalty,” sighs Mill. “But, you know, if your auntie had baws and all that.” Larsson swept an immaculate finish past Derek Stillie with his right foot, then did the same thing on his left foot 13 minutes later, before Stiliyan Petrov definitively ended Dunfermline’s resistance with a third at the death. The dream was over, and so, it soon transpired, was Calderwood’s time at DAFC.

Thomson remembers the shock news souring the mood on an end-of-season club get-together in Magaluf that doubled as his stag do, while Mill – in what might be the most early 2000s anecdote of all time – was compelled to ring his mate Ewan’s landline for an hour-long conversation with Ewan and Ewan’s dad railing against the injustice of it all. Calderwood was off to Aberdeen, the club that had just sacked Steve Paterson after finishing nearly 20 points behind Dunfermline in 11th. “My dad spoke to David Murray when he got the Dunfermline job, and there was an understanding that if he did well, he would eventually get the Rangers job,” Scott explains. “He’s always said he’s a Rangers supporter, so that was one of the main reasons he came back. By then (2004) the Rangers job was gone, but he’d had to take a pay cut at Dunfermline and was sick of some of the things going on behind the scenes, and that’s when Aberdeen came in. He knew, with the team he had, they could have won that final, and the thought that they’d never have that chance again was what hurt him most; not so much for himself, but for his players.”

Calderwood would lead the Dons to five top-six finishes and the last 32 of the UEFA Cup, but back on the Halbeath Road his former club were going through a painful period of downsizing. Within a year of the defeat at Hampden, Stillie, Skerla, Bullen, Nicholson, Crawford, Brewster, Gary Dempsey and Richie Byrne had all moved on, leaving Thomson as captain of a somewhat understaffed and demoralised ship.

“It was a very strange couple of seasons after that, no disrespect to the players that were coming in. The mentality for me as a defender was always: we have Crawford and Brewster, if we lose a goal, we’ll score two or three anyway. Then suddenly it became: if we sneak a goal, we’ll hopefully win 1-0. It was much tougher.” The Pars defied the odds to reach two more cup finals, losing to Celtic in both, but toiled in the league and were eventually relegated in 2007. They have spent just one season in the top flight since then, and will be playing in League One next season after losing to Queen’s Park in the playoffs.

As for Calderwood’s relationship with the fans, while it certainly wasn’t the best in the years immediately following his move to Pittodrie, those wounds had long since healed by 2017, when he bravely made his diagnosis public for the first time. “The fans were always good to him, even if we went for something to eat or a few drinks in Dunfermline,” says Scott. “He had his house in Torryburn and never wanted to leave there, he even had part of the old Dunfermline pitch in his back garden, the last grass pitch, before they laid the plastic one. It was great, the best garden in the estate! I think he still had it when he was managing Aberdeen. A lot of times people respect you more for what you’ve done a few years down the line, when they see what’s going on now and start hearing the real stories about what happened back then. That’s football. It’s difficult, because I’m over here and you don’t always hear that much, but I know a lot of people are finding it really hard seeing what’s happening to him.”

Thomson says: “I stay in touch with him through his partner Yvonne, I ask how he’s getting on and when I’m sent any photos of me and the Gaffer, I’ll always send them on. Craig [Brewster] had come up to see him in Glasgow, and he phoned me after and said, ‘Nipper, he didn’t know who I was.’ That’s when we knew it was serious. I phoned him, although it was his partner I was speaking to, and she said, ‘When I say your name, a big smile comes on his face.’ The same when Brewster or any of the other players get mentioned. He’s with us, but he’s not, and it’s tough listening to that, especially when he’s still so young.”

The question of legacy is a complex one. Ultimately there is no trophy, no crowning achievement, to hang your final assessment of the Calderwood Dunfermline team on, but that’s also because of the strength of their era relative to other eras in recent Scottish football history. From Calderwood’s 2-4-4 to the sums being done by Yorkston and majority shareholder Gavin Masterton in the boardroom, there was a recklessness to the whole project which meant it was always likely to blow up sooner or later. But has any other team not from a major city had such a sustained impact season after season in the Scottish top flight this century? Or entertained us so thoroughly? Mill doesn’t think so.

“It’s one of these questions you can never answer, but if we had that team now, or if we had it the season Aberdeen pushed Ronny Deila’s Celtic relatively close, we could have won a couple of cups and been not far off winning the league – that’s how good we were,” he concludes. “We just timed our good team very poorly. It’s almost a ‘what if’ team, because what if we clung on and won the Scottish Cup? What if the financial problems hadn’t hit in February of that season? What if Brewster had been capped by Scotland and started up front alongside Crawford? There’s a lot of things that should have happened that didn’t, and a lot of things that did happen that shouldn’t have. But in sheer footballing terms, there’s no doubt that was the best time since the 1960s, and that Calderwood was our best manager since Jock Stein.”

If the chances of a big paintballing reunion any time soon for Dunfermline’s class of ’04 are slim, it’s not because the camaraderie that once bonded them has now faded away. It’s due to so many of them – Bullen at Ayr United, Crawford at East Fife, Stewart Petrie at Montrose, Darren Young at Stirling Albion, Skerla back in Lithuania – now being managers in their own right, in what might just be the most significant legacy of Jimmy’s time in West Fife after all. The one place they can all be found together is the least 2004 setting imaginable – a thriving WhatsApp group chat.

As for Nipper Thomson, he has taken the rather less conventional route of co-founding his own highly successful production company, MBP Films, based in Edinburgh. But his love for all things Pars is still there when he wanders down Halbeath Road and takes his seat in the Main Stand on a Saturday afternoon, underscored by a lingering regret about what might have been on another Saturday afternoon 18 years ago.

“I just look back and think, ‘How did we not win anything?’ I know we had bad injuries at times, I certainly did personally. Even with all the injured boys in the team we might have got stuffed in the cup final, you just don’t know. But it’s a big regret of mine. I say to people when they ask me about it, I just wish we’d won something. We deserved to with the football we were playing at the time.”

This article first appeared in Issue 24 which was published in June 2022.

Issue 34
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