Former Manchester United transfer chief names 'most difficult deal' he completed - it will surprise you

Tom Keane only worked as Manchester United head of football negotiations for a matter of months, but it was a whirlwind experience that gave him priceless experience. Three years ago, he was appointed in a temporary consultancy role to offset the departure of the former director of football negotiations Matt Judge in the 2022 summer transfer window.

United effectively had to fit a year's worth of planning into just 16 weeks ahead of the window as they looked to hit the ground running under new manager Erik ten Hag. It was a summer that saw six new arrivals at Old Trafford, including the huge deals to sign both Casemiro and Antony.

Lisandro Martinez and Tyrell Malacia both joined from the Eredivisie after input from the coaching team, while Christian Eriksen signed on a free and Martin Dubravka joined the club on loan. Keane effectively moved into the club's Carrington training complex to complete those deals, though there was one move in particular that proved to be more difficult than the rest.

Tahith Chong sale to Birmingham was difficult

Manchester United had a busy 2022 summer transfer window that saw six new arrivals at first-team level and four senior players sold. There were also five players released, as the likes of Paul Pogba, Edinson Cavani and Juan Mata were not offered new contracts by the club.

It meant a lot of paperwork for Tom Keane to sort in his role as head of football negotiations, though one of the most difficult deals was the sale of academy graduate Tahith Chong to Birmingham City. Having spent the previous season on loan with the Championship club, the Dutch youngster made his move permanent for £1.5 million three years ago after lengthy talks between the two clubs.

"I remember one of the most difficult deals I worked on was Tahith Chong," Keane told The Overlap Breakdown. "He signed for Birmingham permanently, and you've got that disparity, I can't remember what he had left on his contract but what he was earning at Man U and then what he was going to earn at Birmingham. You're just trying to bridge that gap, then you're also dealing with a club where it's a good opportunity for him, but they couldn't potentially, on the face of it, match the valuation. Then it's my role to work out what's a compromise or a scenario that can work for everybody. So they were actually some of the more difficult ones.

"Then you had the players coming in like Casemiro, who was obviously a marquee signing. I remember the debates about that position and who they were going to sign, they were lengthy and good debates, stress testing those signings. My experience was every signing was stress tested and debated before a move was made. With him for example, he had three years left on his contract at Real Madrid, it wasn't necessarily the most difficult player contract to do because if you are going to take a player out who has just won the Champions League with Real Madrid and got three years left on his contract, you pretty much know what you are paying - the contract is there in front of you. It was the less high-profile ones that were more challenging."

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