Steve Cotterill admits he had his doubts over Convers Sports Initiatives (CSI).
But he never dreamed the regime of the owners who once employed him would result in Pompey being taken to the brink of liquidation.
Cotterill was the manager when CSI took over the Blues on June 1 last year.
The group promised to create a stable club and implement a five-year plan consisting of both a training ground and new stadium.
Pompey’s boss was also given permission to recruit players, with seven signed during the summer – the majority for transfer fees.
Cotterill quit Fratton Park in mid-October after being head-hunted by Nottingham Forest.
Barely six weeks later, CSI entered administration, launching a sequence of events which today has left Pompey in its current form facing extinction if a buyer cannot be unearthed within the next month.
Cotterill insists he had his concerns over CSI trio Vladimir Antonov, Roman Dubov and Chris Akers when he was in the Pompey hot seat.
The 47-year-old claims he spent just 20 minutes in the company of majority share holder Antonov during the five months they were together at Fratton.
Yet, it was CSI’s overall handling of the club which raised Cotterill’s misgivings.
It is a touch of irony that Pompey end their Championship stay with a trip to Cotterill’s Forest tomorrow.
And for the manager who played such a crucial role in keeping the Blues in England’s second tier last season, it’s a visit which is tinged with sadness.
Cotterill said: ‘It’s really sad what has happened to Portsmouth. The fans were a different class to me when I was there.
‘Their supporters have had more bad owners than good. I really hope someone comes in and has the love, care and affection for the club so it can go from strength to strength again.
‘CSI came in during the summer and it seemed the club were having fit-and-proper owners.
‘Even as an ex-manager, it is really tough to see what has happened. It is a terrible, terrible shame.
‘But I always felt that something was always not right when they were there.
‘I could never put my finger on it, it was pure gut instinct. I am not talking with hindsight here, either.
‘For a start, it was very difficult to get an answer off them about anything.
‘When they took over the club I had no detailed conversations with them. As manager, that was very frustrating.
‘I never spoke to Antonov for any more than 20 minutes in total for the five months we were there together.
‘I spoke to Dubov on a bit more of a regular basis, but it was not an ideal situation.
‘As people, to me, they seemed always on an emotional rollercoaster and I don’t think that brings stability to a football club.
‘Without doubt, that influenced what was going on around them. You can’t run a club like that, it certainly does not allow you to manage.
‘I was never, ever sure of anything. Something was not quite right there.’
Michael Appleton replaced Cotterill on November 10 last year.
Appleton inherited a squad largely assembled by his predecessor the previous summer and a Championship wage bill approaching £12m.
Cotterill played no part in deciding contracts, transfer fees and salaries during his stint, though.
And when the CSI regime imploded, it left Pompey with an unsustainable wage bill as the club struggles to stay afloat.
Administrator Trevor Birch is seeking to slash that by around 60 per cent, bringing the annual wage bill down to £5m.
Cotterill, though, maintains he improved the playing staff.
He added: ‘I feel for Michael. I know some of the pit falls he is up against and hope he gets the chance to rebuild it.
‘In the end, I felt I was putting a good squad together there, a decent mix of age and experience, and it would have improved again over the summer.
‘I brought in people like Jason Pearce and Stephen Henderson, young lads I got for bargains who have done really well.
‘We needed more goals in the team and that was supplemented by Erik Huseklepp, Luke Varney and David Norris. I also signed Greg Halford.
‘Then there was Marko Futacs, who originally came on a week’s trial and has done well.
‘We even made £2m and got Liam Lawrence and Dave Kitson in exchange for Marc Wilson the year earlier.
‘I have a lot of close friends that still work at Portsmouth and I still speak to the players on the odd occasion.
‘It is a terrible shame what has happened there. It’s a really good football club with really good fans.’