As the only other home-grown Liverpool captain to lift the European Cup, Phil Thompson has more than an inkling about how Steven Gerrard is feeling today.
When the time came for Thompson to leave Anfield after 15 years, it was for Bramall Lane rather than the Bernabeu but, having worked as assistant manager during Gerrard's rise to prominence, he understands how tough it will be to walk away.
The new Liverpool manager, Roy Hodgson, claims that he held "positive talks" with Gerrard, 30, before his captain headed off on holiday. But even though that was perceived by some as an insistence that the midfielder will stay, it is still unclear what he plans to do.
This is not the first time that the new Real Madrid manager Jose Mourinho has put Gerrard in this position but at least Liverpool looked competitive when Gerrard saw fit to reject Chelsea's advances.
Hodgson takes his new squad to Switzerland on Wednesday, with the futures of Gerrard, Fernando Torres and Javier Mascherano remaining a cloud of doubt ahead of the season.
Gerrard is due to link up with the squad the day after next Saturday's friendly with Al-Hilal in Austria, with their Europa League campaign due to start on 29 July.
Thompson, who does not expect Internazionale target Mascherano to return to England, is hopeful that unfounded but painful rumours about Gerrard's private life do not make him request a move.
"I feel for Steven very much and I wonder whether it's a football thing that might drive him away or the rumour mill which has been in overdrive," Thompson said. "It would be quite awful if he went, because Steven has carried his football club for the last seven years. I'd like for him to look at it this way; he is 30, has spent all his life with Liverpool, he's been good for the club and the club have been good for him.
"He's won everything except the League title, so is it going to be worth as much to do it at Manchester City or Chelsea? To actually live that dream? No, it wouldn't. The only other one is Real Madrid and he's not going to win the English Premier League there, is he?
"For me, leaving was awful. I went to Sheffield United at the end of my career but when that decision came only going on loan was difficult enough. But to make that break was heart-wrenching, to know that you're not going to pull that shirt on and do your stuff again, and that will be the biggest thing for Stevie. I think he will have made his decision."
Though he insists the club was at a lower ebb when Bill Shankly took over in 1959, Thompson cannot remember expectations being as low at Anfield and says Champions' League qualification will be a "tall order".
He feels a Spain victory in the World Cup final this evening will be a major help in Hodgson's attempts to keep Torres. "I know Torres has not played well this summer but he will be in a better frame of mind," he added.
"It's going to come down to Roy Hodgson persuading him, Stevie and Mascherano, 'stay with us, bear with us for another 12 months and we won't stand in your way if I'm proved wrong'."
Phil Thompson is an ambassador for The Standard Chartered Great City Race 2010 on Thursday 15 July. Go to www.cityrace.co.uk