And he has revealed in an AFC Bournemouth club podcast how the Blues boss attempted to offload him in the final days of the January 2019 transfer window.
Pitman is regarded as one of the Blues’ finest strikers since they left the Championship a decade ago, with 42 goals in 99 games.
However, his three years at Fratton Park were often impacted by a fractious relationship with the manager who recruited him from Ipswich in July 2017 – Jackett.
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For two lengthy periods he didn’t train with Pompey, including the final six months of the 2019-20 season when he worked alongside Bournemouth Under-21s.
And the 34-year-old has lifted the lid on their relationship.
‘I really enjoyed it, especially in the first season, I was playing week in, week out, that was when I played at my best.
‘The 2019-20 season started all right, in pre-season I scored seven times, I had come back really fit, ready to kick on, then for the first game I didn’t start.
‘I didn’t really kick a ball until mid-September, when the manager (Jackett) was under a little bit of pressure. He kind of turned to me and didn’t say anything, but felt it was the last-chance saloon for him.
‘So I came back into the team, scored a few goals, then got injured – and that was it really for me (at Pompey).
‘He had actually done it the season before (2018-19), nobody really knows that. I got a call on January 30, it was the night Bournemouth beat Chelsea 4-0 (January 2019) and I was sat watching the game.
‘I got a phone call from him saying “I’m bringing in two forwards, you can go if you want”. I said “No, I’m all right, thanks”, that kind of thing.
‘So he tried to get me to leave. Then, for two or three weeks, I wasn't involved, we weren’t winning any games, so he had to bring me back – then I was captain at Wembley (Checkatrade Trophy).
‘He’s a strange bloke.’
Following Pompey, Pitman spent the 2020-21 season at Swindon, where he netted twice in a 3-1 victory over his former club in April 2021.
Last summer he joined Bristol Rovers, before moving on loan to Eastleigh in February for the remainder of the season.
He added: ‘Ipswich and Pompey were both good clubs, they were big clubs, and things were done right there, to be honest.
‘Bristol Rovers were literally the same, they were doing things properly, but Swindon was a strange club.’
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