Curious case of James Maddison and why Man Utd transfer never materialised

19 February 2023 , 06:00

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James Maddison has regularly been linked with a move away from Leicester (Image: Getty Images)

James Maddison is set to face Manchester United for the 10th time in his career on Sunday afternoon - three years on from when he was 'expected' to become a Red Devils player.

The 26-year-old is in the form of his life at Leicester, having scored nine goals and chipped in with five assists in just 16 Premier League matches this season. Maddison also earned himself a place in the England squad at the World Cup as Gareth Southgate rewarded the attacking midfielder for his excellent start to the campaign.

But Maddison didn't play a minute in Qatar as Mason Mount and Jack Grealish were amongst those preferred in that position - something that was criticised by fans and pundits alike. Since recovering from a knee injury he picked up at the tournament, Maddison has scored twice and provided an assist in four games, and put in a superb performance against Tottenham last week as he led the Foxes team out as captain for the first time.

The former Norwich playmaker is one of the most in-form midfielders in the division, and with less than 18 months left on his contract, Sunday afternoon presents him with the perfect chance at Old Trafford to prove why he is so highly-rated. Newcastle, Manchester City and Spurs have been linked with a swoop for Maddison in recent months, but United were the first to express real interest during his second season at Leicester.

Back in October 2019, The Athletic reported that Maddison was set to become a United player within the next year. They stated that the positive relationship between then-United chief Ed Woodward and his opposite number at Leicester, Susan Whelan, may have proved to be the catalyst to get the deal concluded in the next 12 months.

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James Maddison was close to moving to Manchester United in 2019 (Getty Images)

United were keen to add another creative midfielder to their ranks as Ole Gunnar Solskjaer tried to bring in some much-needed flair to the squad. But the Red Devils opted to sign Bruno Fernandes from Sporting Lisbon in the following January transfer window instead - a move that has proved to be successful.

The Portuguese star has scored 57 times in 161 games since his big-money switch to Old Trafford. It could have a been a whole lot different if United had got a deal over the line for Maddison, however, and that looked the most likely outcome in 2019 as the Red Devils battled with Liverpool and Manchester City for his signature.

Fast forward to February 2023 and Maddison is still a Leicester player, having helped guide the Foxes to back-to-back fifth-place finishes and FA Cup glory. Brendan Rodgers' side also reached the semi-finals of the Europa Conference League last season, with Maddison scoring the equaliser in the win over PSV in the previous round.

Should James Maddison move on from Leicester? Have your say in the comments!

James Maddison celebrates after scoring against PSV last April (Getty Images)

Maddison has been a key cog in the Leicester wheel over the past few years but there are fears amongst Foxes fans that his time at the club is coming to an end. Rodgers confirmed on Friday that Leicester are still in negotiations with Maddison's representatives over a new contract but no progress has been made.

He said: "It's been a conversation the club have been having for a while. His contract is clear where it's at. For me, it's about making sure James is playing at the best level he can be. He's staying available and fit.

"It'd be great [if he signed a new contract]. He's a top player in the league, he's shown that in his time here gradually. You can see that development take place. We improve players and give them great conditions to work in. But I won’t be begging a player to stay. They get great support here and if they’ve been here, they understand what the club is about."

James Maddison earned a spot in the England squad but did not feature at the World Cup (AFP via Getty Images)

Maddison, who last signed a new deal in 2019, has just over 12 months left on his deal and could be allowed to leave the King Power Stadium in the summer. United could come back in for Maddison, with the England ace now more experienced and capable in playing in a number of positions; versatility is something Ten Hag likes.

Newcastle reportedly saw a £40million bid rejected for Maddison last summer and were once again linked with the midfielder in January - but chose to spend their money on Anthony Gordon instead. They could come back in for Maddison at the end of the season but a lot may depend on whether they qualify for the Champions League.

Meanwhile, Arsenal are long-term admirers of Maddison, having first been tipped to sign him in the summer of 2021 before they made a move to sign Martin Odegaard. Mikel Arteta wanted the player but Leicester stood firm and kept Maddison amid interest from the north London club.

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If he continues his purple patch during the business end of the season, there is sure to be plenty more interest in the Leicester playmaker this summer.

Kieran King