Tom Naylor's Portsmouth omission can't be much of a surprise - Jackett's always had a ruthless streak

Indeed, Kenny Jackett’s decision to leave Tom Naylor out of Pompey’s League One play-off semi-final defeat Oxford was a major curveball.

It was a huge call from the Blues boss, who instead opted to play Bryn Morris, despite the midfielder not kicking a ball for 14 months.

However, it didn’t quite pay off as Pompey were defeated by the U's on penalties after a 2-2 draw over two legs.

Nevertheless, Jackett’s never been one to shirk away from making significant, if not ruthless, decisions during his three years as manager.

We’ve taken a look at some of the others he’s made...

Immediately freezing out Roberts

It was clear pretty quickly that Gary Roberts wasn't in Jackett's plans after taking over the Fratton Park driving seat from Paul Cook.

Despite being a key figure under the previous boss, scoring vital goals against Carlisle, Hartlepool and Plymouth in the charge to the League Two title, the Liverpudlian quickly found himself in the cold under his new manager.

Roberts was banished to train with the youth team, along with Michael Smith, and forced to watch the 2017-18 League one curtain-raiser from the Fratton Park directors' box.

He'd eventually leave by mutual consent and reunite with Cook at Wigan – where they'd combine to win the League One crowd.

The decision to freeze out Roberts didn't go down well with contingents of supporters at the time.

Meanwhile, the ex-Ipswich man himself said he felt ‘massively disrespected’.

Wing duo’s Black Cats omission

Pompey found themselves a goal down heading into the second leg of the League One play-off semi-finals against Sunderland last season.

Yet Jackett made the call to leave both wing-wizards Jamal Lowe and Ronan Curtis on the bench at Fratton Park.

Granted, both had been quiet in the 1-0 loss at the Stadium of Light, but it was a risky call to drop both danger men who’d netted a combined 29 goals across the campaign.

Instead, Gareth Evans and Viv Solomon-Otabor started on both flanks.

Lowe was introduced on 53 minutes and Curtis wasn't involved at all as Pompey were held to a goalless draw which ended their promotion hopes.

Changing of the armband

On the Monday following a 1-1 draw at Blackpool in August, Brett Pitman and Gareth Evans were called into the manager's office.

Both were told they'd be relieved of respective captain and vice-skipper roles and replaced by Tom Naylor and Lee Brown.

The timing of Jackett's decision was what caused the most confusion.

He stated in pre-season that Pitman was still his captain, despite the forward clearly falling down the pecking order, while Evans was preparing for a campaign playing a support-act role in the team.

Had the decision been in the summer, it would have been fathomable.

However, the timing of the switch left fans bemused.

A shift between the posts

When the teams were announced at Gillingham on New Year's Day, you could only first imagine Craig MacGillivray's omission was due to injury.

However, it soon emerged that the Scot had not suffered a setback.

His absence between the sticks was solely down to a change enforced by Jackett, with Alex Bass instead starting in goal.

MacGillivray had always been selected for League One duty when available, following his arriving from Shrewsbury in June 2018.

He'd become a fans' favourite, his form hadn't wilted and there was no obvious reason why he was dropped.

Instead, it was a 'gut feeling' that Jackett had to change his stopper.

Bass enjoyed a fine run in goal before football was suspended, totting up the highest save percentage rate in the top four divisions.

However, there have been some question marks surrounding his role in both of Oxford's goals during the play-offs - particularly in the second leg.

Pitman’s double exile

Despite being Pompey's top goalscorer in the past decade, there were no hesitations from Jackett to exile Brett Pitman from his set-up this season after the turn of the year.

The striker was as an unused substitute in an FA Cup win at Fleetwood on January 5.

But in the coming weeks, he was banished from Blues training.

Pitman was briefly recalled to the Pompey fray, appearing on the bench three times before lockdown.

But as the Blues prepared for the play-offs, the ex-Ipswich man was again told to remain away from the club’s Hilsea base.

There is a pang of frustration from some supporters Pitman wasn’t on the bench at Oxford to come on and take a penalty given his record.

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