Dick Advocaat remembers being caught between a rock and a hard place in Manchester 14 years ago.
On the one hand, he was leading an exciting Zenit St Petersburg outfit into their first ever European showpiece, looking to crown off a coaching career of his own that would eventually span 34 years and 24 different postings with his one and only UEFA prize.
The trouble was that to do so, he’d have to break the hearts of a club he had built up genuine fondness for during four years in Glasgow.
Even if he won, the Little General knew he’d end up losing to some degree.
By beating Walter Smith’s men at the City of Manchester Stadium, Advocaat realized the affection of the fans who came to idolize him after his Dutch revolution swept through Ibrox, rampaging to five domestic trophies out of six during his first two dominant campaigns in charge , would never be the same again.
In the end, he did was he was paid to do and masterminded Zenit’s moment of glory but it was a victory tinged with regret at what it meant for his old side.
Fourteen years on, Rangers are back at the business end of Europe’s second-tier tournament and Advocaat is just relieved he will not have his loyalties tested this time.
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“It was a difficult match for me,” said the 74-year-old as he looked back on 2008.
“I will always have feelings for Rangers because it was the best period for me of my career in terms of living, the team, the stadium, working with David Murray.
“I had four great years in Glasgow with my family, especially the co-operation I got from Mr Murray.
“It was a great club and a great country.
“So being the coach of Zenit when we faced Rangers in Manchester was difficult.
“I tried to stay calm because I had a great relationship with Walter too.
“But it was tough because of the relationship I had with Rangers, where we won five prizes and also did well in Europe.
“As a coach, though, you always want to win so that’s the way it goes and Zenit got the trophy.
“But I’ll definitely be cheering on Rangers this week. Of course I hope they get the win in Seville. It would be an incredible achievement.
“Frankfurt are a difficult side as they’ve knocked out some quality sides too like Barcelona and West Ham.
“Let’s wait and see – but I want Rangers to win, have no doubts about that!”
Advocaat has extra reason for wanting to see Gio van Bronckhorst match his Euro feats with Zenit.
The current Ibrox boss was Advocaat’s third signing when he took over from Smith in 1998.
The classy £5million midfield recruit would go on to prove his class at Ibrox and beyond, winning a Premier League title with Arsenal, a Champions League winners medal at Barcelona as well as captaining the Dutch to the final of the World Cup in 2010.
But it was Van Bronckhorst’s traits as a man that impressed his former boss as much as his abilities as a player and now a coach.
“I’m so proud of what Gio has achieved because we all know how difficult it is to go that far in a competition of that stature.
“When you see the Rangers teams have faced along the way, you can see they are of really great quality.
“So that says enough about Gio and says enough about what the team has done this year.
“I’ve known him since he was 15 or 16 years old. At that time I was the coach for the Dutch Under-18s so I know him really well.
“He was a great person and a great player. That’s why I liked him so much. That’s the combination you look for when you build a team. It needs both.
“When I moved to Scotland, I bought Gio from Feyenoord and he did really well for Rangers, and not just because we got a lot of money for him when he moved to Arsenal (for £8.5m in 2001).
“We did so well winning trophies in Scotland and playing well in Europe and Gio was key to that.
“But he was still a young man then – too young to say if he would become a coach.
“However, you knew then he was a great person. He was so down to earth and I’ve always really liked his style.
“What a career he has had – Feyenoord, Rangers, Arsenal, Barcelona and more than 100 caps for Holland. Who else can say that they had that career?
“I’ve been watching a lot of the games since Gio moved back to Glasgow.
“They were a little unlucky in some games in the league but what they’ve done in Europe has been great.
“I know in Scotland if you finish second, then that is nowhere.
“But he’s in the final of the Scottish Cup and the Europa League and that is an unbelievable result for his first year.”
Advocaat was never scared to call it like he saw it.
He famously fell out with Ruud Gullit after hitting the then AC Milan superstar with a few home truths during a half-time bust-up at a 1994 friendly clash with Scotland.
Gullit responded to the row by refusing to travel to the World Cup in America a few weeks later and never played for Holland again.
At Ibrox, there were also disagreements with Lorenzo Amoruso, Jorg Albertz and Andrei Kanchellskis as the fuel coach refused to back down.
And in Van Bronckhorst, he sees a little of himself.
The current Ibrox boss made headlines in his previous job with Feyenoord when he opted to drop De Kuip legend Dirk Kuyt.
“For me, the good thing is he is himself,” said Advocaat. “He doesn’t play games. Gio is the way he is.
“That’s important. Players feel that. They want to be treated fairly.
“Yeah, I like his style as a coach very much.
“Giovanni has a lot of character and is a very honest guy because he tells the players what he thinks, face to face. I like that. That’s the way I was too.
“I really think Rangers did a great job in hiring Gio.”
George Holan is chief editor at Plainsmen Post and has articles published in many notable publications in the last decade.