As a lionhearted centre-half, he skippered the Blues through three relegation battles, emerging triumphant from each gruelling conflict to preserve their Division One presence.
Yet Whitbread suffered an ignominious end.
Following microfracture surgery on his right knee in July 2000, the former West Ham man was never allowed to add to his 158 appearances and three goals.
He departed Fratton Park five months later, initially on loan at Luton, never to return to the south coast.
It was a brutal severing of Pompey ties which centred on Whitbread subjected to a Southsea nightclub assault which left him fearing for his eyesight.
The unprovoked Time & Envy assault inflicted a deep facial gash requiring glueing. Not long after, he moved back to Essex over ongoing concerns for his safety, preferring to commute.
To add insult to noticeable injury, manager Tony Pulis fined Whitbread two week’s wages over the nightclub incident.
The scars still remain.
‘I was a regular under Tony Pulis in the beginning, but, in the summer of 2000, underwent a knee operation and was out for three months. That is where it unravelled,’ Whitbread told The News.
‘One day, the manager said to me: “Why don’t you take some time out? Have a week away and then come back. By that stage you’ll be off your crutches”.
‘It was a good idea. I went to Lanzarote with my friend who had a villa out there. It was a chance to chill.
‘Lo and behold, while I was away, it was announced Darren Moore would be the new club captain. Pulis never told me.
‘Had he said to my face “Whit, I’m going to give the captaincy to someone else”, then I’d have been fine with it. Darren’s a great bloke, I was injured, that’s how football is.
‘But tell me face-to-face, don’t just do it when you’ve made sure I’m not even around.
‘When I came back from the Canary Islands, we were playing Grimsby Town on a Saturday afternoon at Fratton Park, so I went along on my crutches to watch.
‘The boys were going out after the game, in those days we still had that connection of being sociable. Initially I declined, but they kept saying “Come out, come and have some fun with us”. So I did.
‘We ended up in Time & Envy on the seafront. I will always remember it, it was back in the days when cigarette machines were inside and I recall seeing two blokes leaning against it and looking over.
‘It seemed a bit strange, but didn’t think anything else of it.
‘This is the true story, straight from the horse’s mouth. The next thing I knew, there was a punch thrown, knocking me to the floor, and, as I got up, a glass came flying over.
‘It shattered in the middle of my face. My face was a mess. As you can imagine, there was claret everywhere.
‘My immediate thought was “Am I going to lose my eyesight?”.’
The visit of Grimsby on that Saturday afternoon in August 2000 resulted in a 1-1 draw, an outcome which agitated the Fratton faithful.
The News’ then-chief sports writer Mark Storey’s match report read: ‘Pompey fans soaked in years of relegation struggle have grown used to poor matches, but this one was one of the very worst’.
Whitbread and his crutches occupied a South Stand seat, among those 12,511 present for the Blues’ second match of the 2000-01 season.
Hours later he was in Queen Alexandra Hospital after being targeted by a disgruntled Pompey fan.
Whitbread added: ‘Back in the day, players would go out, you can’t keep them in a cardboard box, we’re human beings like everyone else.
‘Gerry Creaney was before my time at Pompey. I don’t know him, but I do know the stories. This was different to the time he was attacked.
‘As players, we’d go out and socialise, yet if we saw any trouble or sensed anything coming, we would either disperse or make sure nothing bad happened.
‘If we had lost on a Saturday, I wouldn’t have been stupid enough to say “Right, I’m going out tonight”. You realise you’re out in a city where everyone knows the players, everyone knows their football club.
‘That wouldn’t be the thing to do. On this occasion, we had drawn, while I hadn’t even played because of injury.
‘That evening, I was standing in the corner, minding my own business. I hadn’t taken my crutches out because I knew I’d be coming off them on the Monday.
‘We weren’t doing anything untoward, there were no women involved, I wasn’t being rude to anyone. Nobody was being boisterous, we weren’t being arrogant, none of that.
‘It later turned out the two men were supporters who got drunk at the game, carried it on, and didn’t like the fact we’d drawn in a disappointing result.
‘The police caught the culprits and, from the gist that I got, it was “We just felt like taking it out on Adrian Whitbread”.
‘Still, it has left a permanent scar down the middle of my head, just above the nose. The doctors did a good job clearing it, glueing it back together. It doesn’t look too much now, but it's there.
‘That was kind of the beginning of the end for me at Pompey. Right there.
‘On the Monday, I went in to see Pulis – and he wanted to fine me two weeks wages.
‘He blamed me for what happened. “Well, go elsewhere for a night out” he told me. But these were my friends. The players, the supporters, I saw them on a regular basis, it’s a very tight-knit community down there, everyone looks after each other.
‘In any walk of life, people ask “Is it safe?”. Never did I think that nightclub would be unsafe, I had been to Time & Envy countless times, supporters had seen me there before.
‘Suddenly it felt that Pulis was using what happened to get me out of the club. When he tried to fine me, I couldn’t believe it. I had done nothing wrong.
‘My time was done with him at Pompey, he wanted to move me on. To him it must have been an easy way to get a reaction from me and get rid.
‘As it turned out, I outlasted him at Fratton Park, but still never played for the club again.’
A Paulsgrove man was stopped inside Time & Envy on the night of the incident and later charged with assault occasioning actual bodily harm.
The incident was reported on the front page of The News under the headline ‘Pompey star hurt in attack at nightclub’.
Yet a ‘scared’ Whitbread subsequently moved out of the Port Solent home he rented and returned to Loughton, Essex.
‘During the week of the court case, which didn’t involve me attending, I woke up to notice the window cleaner doing my windows,’ he said.
‘He was a Pompey fan and said “Hello Adrian, how are you? Your car’s got four flat tyres”.
‘Well, I thought he was telling a joke, so asked what the punchline was. It was no joke, it was true.
‘Overnight, somebody had punctured all my car’s tyres and also scratched it. It scared the living daylights out of me.
‘To this day, I don’t know who was responsible.
‘This was my home and made me realise that people possibly knew where I lived. I was very, very scared and pretty much moved back to London straight away.
‘Suddenly I didn’t feel comfortable living there. I looked elsewhere, so went back to the area I lived while at West Ham.
‘Besides, if I wasn’t playing, I might as well commute every day for training.
‘When Pulis left as manager, Steve Claridge took over. I thought I might have a chance of playing again as I had got on with him in the past. That didn’t materialise.
‘I needed to make a decision and went out on loan to Luton. I wanted to play, especially after injury. If I wasn’t going to play at Pompey, I had to look elsewhere.’
Following a loan spell with Alan Pardew’s Reading that same season, Whitbread joined the Division Two side on a two-year deal in July 2001 .
He went on to total 37 appearances, while had a three-month loan at Exeter, before retiring in April 2003 through injury to his left knee. He was aged 31.
Since then, the former Swindon defender has carved out a strong career in coaching, working at Barnet, Brentford, MK Dons, Leicester, Chesterfield and in Puerto Rico.
Perhaps inevitably, his path would also cross with Pulis once more.
Whitbread added: ‘A year after leaving Pompey, one of Tony’s members of staff, Mike Trusson, called completely out of the blue.
‘Tony had been sacked by then and it was the off-season. Mike said: “Hello Whit, would you be a character witness for Tony Pulis in his court case against Milan Mandaric?”.
‘Well, he’d taken the captaincy off me, fined me after being attacked and got me out of the club!
‘My response was “What do you think my answer is?”.
‘Mike replied: “Do you know what Whit, I thought that would be the answer, but I’ve got to ask”.
‘Some six years later, I was at Leicester City assisting Martin Allen and went to watch Wolves in a League Cup game – and Tony was there.
‘He was Stoke manager by then and it was the first time I’d seen him since all this had gone on. I’d often wondered how I would react should I come across him again.
‘I walked over and shook his hand. I wanted to be a bigger person.
‘My time at Pompey came to a sad end. Apart from my first period at Leyton Orient as a kid, it was the longest I’d been at a club.
‘Since what happened, I have seen Pompey fans up in London when I’ve been socialising and also when back on the south coast and never had any trouble.
‘As a Pompey player, I felt I had a great rapport with supporters. I classed them as my friends, that’s how they made me feel.
‘I don’t think you spend six seasons at a club without having decent people around you and good friends. I felt very, very comfortable and privileged to play for Portsmouth Football Club.
‘However, a supposed fan made it very uncomfortable for me to stay at a place I loved. In one night it had all gone, taken away from me.
‘It was him – and Tony Pulis.’
A message from the Editor, Mark Waldron
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