Portsmouth's 'winter player' swaps Championship for non-league in shock summer switch for ex-Derby and Bradford man

The chance to work under Paul Cook has proven irresistible for Tom Naylor, who has this week quit Wigan for Chesterfield.

It means the midfielder who started 22 Championship matches last term, will be playing in the National League next season.

Signing a three-year deal, the 31-year-old will be challenged to guide the Spireites back into the Football League after falling in the National League play-offs in successive campaigns.

Nonetheless, it represents a surprise move for Naylor, who made 86 appearances and scored seven times during two campaigns with the Latics.

The defensive midfielder was also part of Leam Richardson’s side which claimed the League One title in 2021-22.

Naylor had moved to Wigan in the summer of 2021 on a free transfer from Fratton Park, after three seasons in which promotion frustratingly eluded.

In fact, his shock absence from Pompey’s side for their League One play-off semi-final against Oxford United in July 2020 represents one of the more curious selection decisions in modern Blues history.

Particularly when Kenny Jackett replaced his skipper with Bryn Morris and explained it was down to being a ‘winter player’ rather than a summer performer.

As it turned out, the Blues were eliminated on penalties by the U’s, with Naylor remaining an unused substitute in both behind-closed-doors legs.

Curiously, despite that snub, the former Burton man was restored to Jackett’s midfield for the following season as if the controversial incident never occurred.

However, the Blues manager wouldn’t last the campaign, dismissed in March 2021 following EFL Trophy final defeat at Wembley by Salford.

With Danny Cowley arriving as interim manager, Naylor retained his place, starting every match as Pompey missed out on the play-offs on the final day to finish eighth.

The midfielder was subsequently released, although had made it known he favoured a return up north to be with his family, who had remained there while he represented the Blues.

During his Fratton Park days, Naylor replaced Brett Pitman as captain, won the Checkatrade Trophy and totalled 149 games and three goals.

Now, three years later, he has opted to drop into the National League as he strives to lead Chesterfield back into the Football League.