Milan Mandaric has vowed not to repeat his Pompey mistakes when it comes to leaving Sheffield Wednesday.
The 73-year-old has achieved promotions with three different clubs since his arrival in English football 14 years ago.
The hat-trick was completed after the Owls clinched second spot in League One last weekend.
It has now been six years since Mandaric stepped down as Pompey chairman and sold his stake to Sacha Gaydamak – before taking over at Leicester City. Since then, the Blues’ finances have spiralled out of control under a succession of owners, resulting in two spells in administration.
But Wednesday’s chairman insists he will do everything possible to ensure his current club are left in safe hands when the time is right to move on.
He said: ‘It breaks my heart to see Portsmouth doing not so well after I left.
‘There is nothing I can do but make sure the next owners after me at Sheffield Wednesday are the right people.
‘I will not let what’s happened to Portsmouth happen to Sheffield Wednesday.
‘That will be my other objective – when the time comes.’
Pompey’s relegation ensures the Owls have effectively taken their Championship spot.
And Mandaric can reflect on two very different regimes.
He added: ‘To be honest, Portsmouth was similar (success) but here it is with larger numbers (fans).
‘This club had success before my time but you have to give the people credit.
‘They had a massive club some time ago which fell on difficult times.
‘At Portsmouth, it was different. They were already in administration and were very thankful.
‘We built a relationship of trust and friendship.
‘It took me a couple of years because I was new to England but we got them back where they belong.’