Sheffield United, Barnsley deals couldn’t save Chesterfield but window now provides perspective | OneFootball

Chesterfield have been busy in what could be a 'make or break' January, with Paul Cook adopting a different approach to their January 2018 spending.

Chesterfield are in the middle of a busy January transfer window, having already announced the signings of four players, with Kyle McFadzean the latest arrival to join up with Paul Cook’s squad, as Town look to get their season back on track following four league games without a win.

The Spireites will be hoping to avoid a repeat of their last January transfer window in the EFL back in 2018 under Jack Lester, which ultimately led to Chesterfield’s relegation to the National League.

Club legend Lester, who saw his iconic number 14 shirt retired at the club after scoring 83 league goals in 197 games, took charge in September 2017 after Gary Caldwell, who oversaw Chesterfield’s rock-bottom finish in League One the previous year, was relieved of his duties following a poor start to the season, picking up just five points from the Spireites’ first eight games.

The Spireites entered January hovering precariously, just one place above the drop zone, one point clear of the bottom of the league, and a big winter window was needed to ensure Town’s survival.

Lester’s small budget helped get several loan deals over the line

In January 2018, Chesterfield owner Dave Allen was actively looking to sell the club, which would likely lead to Lester being given a small budget to work with, meaning he had to rely on a number of shrewd signings to help the Spireites stay up.

Having cashed in on Ched Evans in the summer of 2017 for £500,000, Allen was reluctant to pump some of those funds back into the playing budget, with former Brighton striker Chris O’Grady being Town’s marquee summer signing in what was an underwhelming window.

Lester was quick to add to the Spireites’ squad, completing moves for then Sheffield United youngster Aaron Ramsdale, Barnsley youngsters Jacob Brown, Dylan Mottley-Henry, as well as Millwall’s Sid Nelson, all on-loan deals until the end of the season.

The Chesterfield legend also made some permanent signings, bringing in Northampton Town full-back George Smith, Burnley’s Alex Whitmore, Barnsley's Josh Kay, and the experienced trio of Giles Coke, Zavon Hines and Louis Dodds.

Spireites legend Drew Talbot was also brought through the door for his second spell at the club, after leaving for Portsmouth in 2016.

Following these moves, the Derbyshire club looked like they were turning a corner and stunned League Two leaders Luton Town in a 2-0 victory in the middle of January, with five of Lester’s new signings in the starting 11.

However, the faith was short-lived, with Lester’s men going on a run of five straight defeats soon after and, despite impressive wins over Swindon Town and Notts County, Town ended the season losing seven of their last nine matches, which led to their relegation.

Lester would leave the club by mutual consent in late April, and Chesterfield would finish rock bottom of League Two, eight points from safety.

With the club’s financial situation, it would be harsh to look to blame Lester for Chesterfield’s lackluster recruitment, with the former Nottingham Forest striker effectively having to gamble on loaning in youngsters and signing experienced players, who were way past their best.

While Lester did unearth a few gems, with Aaron Ramsdale and Sid Nelson both impressing in Derbyshire, most of his signings were flops, with the likes of Mottley-Henry and Brown looking lightweight in their first season in senior football.

Injuries played their part too, as Mottley-Henry suffered a hernia just two games into his spell, which saw him recalled, and Nelson, whose passion and desire had won over the hearts of Chesterfield fans, suffered a freak injury after colliding with the goalpost, which made him miss the rest of the season.

With injuries to long-standing centre-back duo Ian Evatt and Sam Hird, Chesterfield had no choice but to invest in January, but unfortunately for Lester, a lack of money and quality available options made January 2018 a window and a season to forget.

Chesterfield find themselves in a very different position seven years later

Fast-forward to January 2025 and there are definitely comparisons that can be made between this current transfer window, and the one back in 2018.

Both squads needed investment following long-term injuries to key players, with Chesterfield’s current injury list in double digits, but there are two key differences between the demoralized Town of seven years ago, and the forward-thinking progressive Blues that can be seen today.

The manager and the ownership situation.

Under Allen, Lester was left with a relatively small transfer budget for him to add to his squad in January, but Cook has the backing of ambitious owners Phil and Ashley Kirk, who recently invested £2million earlier this year, with the pair maintaining a brilliant relationship.

Cook told the Derbyshire Times ahead of January:

“I just think it is a really big window.

“I have had a meeting with Ash and Phil (Kirk) this morning and they are so supportive.

“One of the reasons why I stayed at the club was because of them. That is the brutal truth, because of how supportive they are.”

In terms of player recruitment, Chesterfield was Lester’s first job as a manager in the EFL and didn’t have the pull that Cook does, with multiple players calling the 57-year-old as one of the main reasons for joining the Spireites.

The former Ipswich manager has used his knowledge of high-quality players and pull to bring in the likes of Will Grigg, Tom Naylor, Janoi Donacien, among many others, while the only players Lester could attract were local youngsters from clubs higher up the pyramid.

Once again, Chesterfield find themselves in a crucial January window which could make or break their season, but the Spireites are much better equipped to deal with it this time around, which is testament to the progress they have made on and off the field.