The Sheffield United deal that cost nothing but transformed the Blades - Coventry City had to sit and watch | OneFootball

Coventry City picked up midfielder John Fleck on a free transfer, but then could do nothing but watch as he left on one four years later as well.

Picking up a talented young player on a free transfer can be a boon for a club, but as Coventry City found in 2016, it can be frustrating when you lose them without receiving a fee as well.

The 2010s were not an easy period in the history of Coventry. The club fell from the Championship to League Two over these years against a backdrop of protests from supporters as the club's hedge fund owners argued with the local council over ownership of their stadium.

In 2012, they were relegated into League One, and money was tight. But one player caught their attention who was available for a modest fee. John Fleck was the nephew of the former Norwich City star Robert, and his contractual position at his club gave him the option to tear up his contract. Fleck would end up staying four years with Coventry, but his departure would bring frustration as he left for nothing and went on to become a bit of a legend at his next club.

John Fleck signing for Coventry City came about because of the Rangers financial crisis

Fleck's arrival at Coventry didn't come about without some degree of controversy. Fleck had joined the Rangers youth academy in 2005, and made his full debut for them two years later, a month before his 16th birthday, signing a three-year contract extension with them in 2010.

But by 2010, Rangers were in desperate financial trouble and things didn't get any better. In February 2012, they entered into administration, and the transfer of the club from one limited company to another gave their players the opportunity to rip up their contracts and leave. Ten of them did exactly this, and Fleck was among them.

Coventry were not an especially healthy club throughout Fleck's time there. They found life in League One little easier than the Championship, and in 2013 the owners moved the club to Northampton over their stadium dispute. But Fleck was a consistent performer, albeit after a slow start, and in January 2015 he signed an 18-month contract extension with the club, keeping him at Coventry - or wherever they happened to be playing - until the summer of 2016.

John Fleck blossomed at Sheffield United

But by the summer of 2016, Coventry's position hadn't improved a great deal. The club had only lasted a year at Northampton before returning to their home city, but Fleck's four seasons at the club had seen them finish 15th, 18th, 17th and 8th in the League One table, unable even to claim a play-off spot over those four years.

Fleck had struggled for game-time initially, but he blossomed in his final season with the club under Tony Mowbray, winning their Fans' and Players' Player of the Year awards. But this would bring a risk of its own. Fleck was out of contract at the end of the season, and the chaotic running of the club over his time there had clearly left an impression. At the end of his contract, Fleck left Coventry and signed for Sheffield United on a free transfer.

Within the structure of a normally functioning club - and his previous two had been about as far from that as could be imagined - Fleck thrived. He ended each of his first two seasons with the club as their Player of the Year - winning the first of these jointly with Billy Sharp - and winning promotion from League One at the end of 2016-17 as champions. It was a transformative time at Bramall Lane, as the club went on a journey back to the top.

He was also a regular in their team that won a return to the Premier League in 2019, and scored five goals for them throughout the 2019-20 season as Sheffield United surprised everyone by finishing ninth in the Premier League. Fleck would go on to stay at Bramall Lane until 2024, winning another promotion, before losing his place in the Blades team and signing on a half-season loan with Blackburn Rovers for the second half of the 2023-24 season.

But injury blighted his brief time at Ewood Park, and at the end of the season, by this time out-of-contract at Bramall Lane, he moved to Chesterfield, where he remains. In total, he made 278 appearances for Sheffield United over those seven and a half seasons to add to the 182 that he'd made for Coventry City.

All Coventry could do, as Fleck flourished at Bramall Lane, was look on. The Sky Blues still hadn't hit rock bottom by the time he left in 2016. They would come at the end of their first season without him, when they were relegated into League Two. Fleck, meanwhile, had become a transformative player for Sheffield United, a key performer in a team that won two promotions in three seasons.

The club have been revived since then, and by the time that Fleck signed for Chesterfield they were a Championship club again, but considering how badly run they were at the time that he played for them, Coventry might even consider themselves somewhat fortunate to have held onto such an accomplished player for four years, not that this would have made anyone feel much better when he left for nothing in the first place.