What might have happened in the summer 2017 transfer window had Paul Cook not left Portsmouth for Wigan

It's something that Robbie Blake firmly believes.

The ex-Pompey coach is adamant successive titles would have been yielded had Paul Cook not left the driving seat in May 2017.

The Liverpudlian had guided the Blues to the League Two title – but left his post just 26 days later.

A whirlwind period culminated in Cook and the majority of his backroom staff departing for Wigan three years ago last Sunday.

On the flip side, some close to Cook claim not enough effort was employed to keep their manager, who privately harboured concerns he would be incompatible with the incoming owners.

Blake feels had Cook stayed then the League One trophy would also adorn the Fratton Park trophy cabinet.

Instead, it would reside in the DW Stadium, with the Latics winning the title by two points while Pompey finished just outside the play-offs.

From left: Gavin Massey, Paul Cook and Gary Roberts.placeholder image
From left: Gavin Massey, Paul Cook and Gary Roberts. | Freelance

So, hypothetically, how would the 2017 summer transfer window played out for the Blues had Cook remained in charge?

We’ve taken a look…

Which players have arrived?

A deal for Nathan Thompson was already down the line when Jackett took the helm – and one he opted to go through with.

But another player who seemingly was in the offing to sign was Gavin Massey.

The winger was linked with Pompey shortly after Cook departed – and would go on to join Wigan on a free transfer from Leyton Orient.

Massey was a key player for the Latics, registering six goals and five assists in 50 appearances as they claimed the third-tier crown.

The former Colchester wide man has continued to be a regular in the Championship.

Another who looked like he’d have donned the star & crescent was Christian Walton.

Blues goalkeeping coach John Keeley had done his due diligence on the Brighton man, who had impressed on loan at Luton and Southend the previous campaign.

Pompey had held talks with Walton - but he'd instead follow Cook to Wigan.

Jackett instead moved for Luke McGee from Tottenham.

The most exciting player who perhaps might have become a Blues player is now widely regarded as the best player in League One – Ivan Toney.

When Cook left, Conor Chaplin was the only striker who appeared to firmly be in his plans.

Eoin Doyle's loan from Preston had expired, while Michael Smith and Curtis Main were both out of favour.

Meanwhile, Nicke Kabamba had made only four outings after he arrived from Hampton & Richmond with Jamal Lowe the previous January.

At Wigan, the former Sligo boss recruited Toney on loan from Newcastle – and who's to say he wouldn't have done the same at Fratton Park?

In fairness, Jackett's recruitment in the forward department was hardly lacklustre.

He pulled off a major coup to bring Brett Pitman to PO4 from Ipswich that summer.

He’d bag 25 goals in all competitions, only to be outscored by Peterborough’s Jack Marriott as the division’s top marksman.

Oli Hawkins was also recruited from Dagenham and has proven to be an adept option.

Meanwhile, Toney didn't enjoy a prolific spell at the DW Stadium, scoring only six goals in 28 games before his spell was cut short midway through.

Who could have stayed?

By the time Jackett had taken charge, Michael Doyle had already decided to return to Coventry.

Meanwhile, the opportunity to play in the Championship for Sheffield United proved too tempting for Enda Stevens.

But one regular starter from the previous campaign who quickly found himself out of Jackett's plans was Gary Roberts.

The creative midfielder had bagged 20 goals in 80 appearances after reuniting with Paul Cook following their time together at Chesterfield.

Roberts had been key when Pompey clinched the League Two title.

Yet the ex-Swindon man was forced to train with the youth team, omitted from the final pre-season friendly of the summer against Bournemouth and then watched the curtain-raiser victory over Rochdale from the stands.

After Roberts’ departure by mutual consent, he again reconvened with Cook at the DW Stadium, where he still playing aged 36.

Had Cook stayed at Fratton Park then it’s fair to say Roberts would have, too.

As Jackett actively looked to reduce the average age of his side – something sections of fans concurred with – it meant Carl Baker also fell out of favour.

The winger had plundered nine goals en route to fourth-tier glory from a right-wing role.

But after a fleeting reinvention as a central-midfielder, he too was allowed to leave for Indian outfit ATK.

Moreover, there might have been contract offers for players Jackett opted to release.

Stanley Aborah displayed glimpses of his talent in four outings, while Amine Linganzi had made 23 appearances.

Jackett instead looked to blood in youth in central midfield, in particular, giving more frequent first-team opportunities to academy graduates Ben Close and Adam May.

Who could have left?

In terms of the players who were out of favour under Cook, there weren't too many that were given a second chance under Jackett.

Michael Smith left by mutual consent for Bury, likewise Tom Davies to Coventry.

Meanwhile, Curtis Main (Millwall), Drew Talbot (Chesterfield) and Milan Lalkovic followed midway through the campaign.

News you can trust since 1877
Follow us
© 2026 Iconic Media Group Ltd. All rights reserved.Cookie SettingsTerms and ConditionsPrivacy notice