A footballer’s career is full of sliding-doors moments, particularly when it comes to the business of transfers that do and don’t happen.
A number of players involved in this Saturday’s Scottish Cup third round clash between Dundee and St Johnstone will have reason to contemplate the turn of events that has meant they are not on the other side.
There’s a Saints defender who left the Dark Blues as a youngster, a Dundee midfielder who became a side-story to the Tommy Wright-Neil McCann feud and five others who came close to appearing in a different shade of blue.
Eric Nicolson looks back on some transfer tales that make for weekend cup sub-plots.
It was the summer of 2018, Partick Thistle had been relegated and Dundee were looking for a new left-back to replace outgoing Kevin Holt.
Top of Dens boss Neil McCann’s wish list at one point was understood to be Booth.
He had a one-year option on his contract at Firhill, which the Jags couldn’t afford to trigger when they were cutting their cloth after going down to the Championship.
McCann chose to sign Nathan Ralph instead and then brought in Calvin Miller on loan as cover.
Booth did end up playing his 2018/19 football in the city of Dundee – but at Tannadice rather than Dens.
One year later he was on the move to Bury and, after their sad demise, returned north to St Johnstone where he has spent the last season-and-a-half.
Ralph may not have been the worst player in that Dundee side but there is no doubt that Booth would have been a better bet than either him, Miller or whoever else got thrown in over the course of a wretched Premiership campaign that culminated in relegation.
Booth himself was in and out at United and then his move south was an unmitigated disaster through no fault of his own.
But now he’s a Premiership regular in Perth and has a Betfred Cup winners’ medal in his possession. Things haven’t worked out too badly, have they?
There are a few of the current St Johnstone players who were part of the club’s academy as a youngster but, perhaps surprisingly, local boy Gordon isn’t one of them.
The first professional club to sign the imposing centre-back was in fact Dundee.
Gordon, who caught the eye of Dens scouts playing for Bridge of Earn after starting out at Letham, only had a short career in dark blue. He left the club after their second administration.
His coaches moved to Raith Rovers and Gordon was signed for the Stark’s Park club at under-14 level.
John McGlynn subsequently took Gordon to Hearts before he found his way back to the club he supported as a child in 2015.
The stories of points deductions for Dundee and senior pros being released were understandably the headline ones back in 2010. But Gordon’s career path is a reminder of the young talent that was lost to Dundee and, in other cases, lost to the professional game entirely.
Had it not been for the financial implosion, you would have expected him to progress through the pro-youth set-up there.
For the player himself, local lad winning a cup for his team and his town is the stuff of fairy tales.
May’s return to Perth in 2019 turned into the on-off saga of the close-season.
Once Aberdeen manager Derek McInnes made it clear the Saints 2014 Scottish Cup hero would be available for transfer despite having two years left on his Pittodrie deal, he immediately became Tommy Wright’s number one target.
The Northern Irishman wasn’t alone, though.
James McPake, with the help of his assistant and former Saints team-mate of May, Dave Mackay, were given the chance to persuade him to come to Dens.
It all dragged on until the end of August, with McPake putting on record that the package Dundee put together was “as good an offer as I have seen at this football club”.
May’s heart was set on a McDiarmid Park return, however.
May was the prodigal son for Saints and Kane Hemmings ended up being Dundee’s own homecoming hero that summer so everyone was happy in the end.
He hasn’t had many starts of late for Callum Davidson but his career has been revived after a frustrating time at Aberdeen and he set-up Glenn Middleton for the goal that secured top six football and the chance of qualifying for Europe.
It is understood he has an option to extend his contract for a further season and it would be a big surprise if he didn’t stick around.
Rooney wasn’t short of pre-contract offers in January 2020 and early in the month McPake was optimistic that the full-back would be heading to Dundee when his Inverness deal ran out in the summer.
However, Wright had Premiership football to offer the former Dunfermline and Queen’s Park man and he became the legendary Saints manager’s last signing before he left Perth in May.
With Wright gone and Davidson in charge, Rooney struggled for game-time early in the season, Danny McNamara being preferred in the right wing-back role, and he struggled for form when he did get the chance to play.
At that point you wouldn’t have been shocked if somebody had said he would soon end up back in the Championship – possibly even at Dundee – but what has followed has been one of the Scottish football feelgood stories of the season.
Rooney scored in the quarter-final, semi-final and final of the Betfred Cup for Saints and has been talked about for a Scotland call-up.
If he’s going to the Championship in the near future, it will be to the English not Scottish one. This has been a career-changing season for Rooney and McPake, who has chopped and changed at right-back, will be the only one thinking ‘if only’.
The Saints boss knew what he would be getting, having worked with Ashcroft at East End Park as Stevie Crawford’s assistant, and was impressed again when he spent time in Perth as a trialist.
A Championship tried and tested centre-half in his mid-20s was always going to be in demand, though, and a combination of Dundee making an early contract offer and the greater prospect of first team football at Dens than McDiarmid proved a persuasive combination.
In the end, Davidson decided to strengthen his squad in other areas, with Booth and Rooney providing central defensive cover.
There should be none of those all-round.
Ashcroft was right to suspect he would be fourth choice centre-half with Saints and want more for himself at the peak of his career.
A player who prioritises regular action should never think about ‘what might have beens’. He’s too good to be a back-up and has proved that with Dundee.
From Saints’ perspective, Davidson has been fortunate that all of his centre-backs have steered clear of injury for the vast majority of 2020/21. If Jason Kerr, Jamie McCart or Liam Gordon had been sidelined for a month or more, there could have been an issue.
Making a strong, early pitch for Ashcroft helped McPake get his man and that was undoubtedly the case when it came to signing Byrne a year earlier.
Saints, along with Motherwell and St Mirren, were keeping tabs on the then Livingston midfielder but by offering Livingston a five-figure sum and the player the security of a three-year contract, McPake and Dundee were able to trump the rest.
Faced with accepting the offer or playing the long game, Byrne chose the former.
Last season was a frustrating one for the former Dunfermline man, who was in and out of the Dundee side, and there was even talk of a swap with Ross Callachan last January when he arrived at Dens on loan from Saints.
Not an easy one, this.
You can’t regret something that wasn’t offered. Byrne was quite right to snap up the deal on the table even though it was likely a top flight club would have made a rival bid before the end of the 2019 summer transfer window.
He had been one of the best in his position in the Premiership the season before, after all.
Football-wise, though, it would be a push to say it has been a great move. Byrne is too good a player to be warming a bench in the Championship and his skillset – as he showed with Livi – is ideal for a disciplined holding midfielder role, possibly even more so in the top flight than the second tier.
If he moves in the summer, don’t be surprised if it’s back up a division.
Not long after the infamous Dens Park touchline and tunnel incident of 2018 involving Wright and McCann, Saints informed Dundee of their intention to speak to McGowan, who was due to be out of contract that summer.
Was there a bit of mischief-making? That will have to wait until Wright pens his memoirs.
Anyway, it mattered not. Before talks could take place, McGowan swiftly got the offer of a deal that met his wishes and it was duly signed.
McGowan, a dressing room and on-pitch leader, is part of the furniture at Dens and you could see him finishing his playing career there and maybe even moving on to the coaching staff.
But if you’re talking in pure football achievement terms there is no comparison between the relegation season and two years in the second tier he has endured since extending his Dundee contract versus what has happened across Tayside.
In that summer’s window, Wright recruited Matty Kennedy, Drey Wright and Danny Swanson so he got the extra creativity he was looking for and certainly had no cause to regret missing out on McGowan.