Pompey completed their quest for Championship football in April as they booked their return to the second tier of English footbal as League One Championships.
It proved to be a relentless pursuit that was initally started in the summer of 2017, after Paul Cook’s Blues secured the League Two title thanks to a 6-1 win over Cheltenham on the final day of the 2016-17 season.
Since then, Pompey have turned to three different managers/head coaches to achieve their goal - Kenny Jackett, Danny Cowley and John Mousinho. However, it was Mousinho who finally delivered the prize as his side went above and beyond what his two previous predecessors’ teams could achieve.
That guarantees him a place in Fratton Park folklore. But it’s fair to say, his achievements might not have been entirely possible had it not been for some of the work undertaken at Fratton Park in the years building up to this season’s success. As director Eric Eisner often points out, it’s process that has been built and allowed to take shape over time.
In that sense, both Jackett and Cowley have helped shape Pompey’s rise - not that they would want any of the credit - with the former kicking it all off under the Eisners.
Mistakes were made along the way, as we all know. But with the latest transfer window fast approaching, what tranfer successes and failings were there under Jackett’s charge? We’ve assessed his 50 transfers during his near three years at the Fratton Park helm - and this is what we’ve decided, with each player given a rating out of 10. See if you agree or disagree.
17. Louis Dennis - 4/10
Pompey stats: 8 appearances, 1 goals. Verdict: The forward endured a frustrating one season at Fratton Park after arriving on a free transfer from Bromley. He made just eight appearances in total, with only one coming in the league, while he was axed for the Checkatrade Trophy semi-final and final. Showed his talent when he was given chances in the Checkatrade and reserves but couldn’t force his way into Jackett’s plans. | National World
18. Tom Naylor - 8/10
Pompey stats: 149 appearances, 13 goals. Verdict: Signed from Burton on a free transfer, the combative midfielder's time at Fratton Park will always be remembered for his shock absence from the Pompey’s side for their League One play-off semi-final against Oxford United in July 2020. It represents one of the more curious selection decisions in modern Blues history. The current Chesterfield player gave his all for Pompey and was ultra-competitive for the Blues. | National World
19. Craig MacGillivray - 8/10
Pompey stats: 135 appearances. Verdict: Before his Blues exit in 2021, the former Shrewsbury reserve established himself as Pompey's finest goalkeeper since departing the Championship 2012. He served the Blues with distinction, which earned him The News/Sports Mail’s Player of the Season in his final campaign. | National World
20. Andy Cannon - 7/10
Pompey stats: 79 appearances, goals. Verdict: The midfielder proved an asset during his time at the club, after arriving for an undisclosed fee from Rochdale in January 2019. A talented player, particularly in his last season when he was played as a No10. However, there's an argument that he didn't hit the heights that he would have desired in terms of goals and assists. | National World