The summer transfer window is just under three months away from opening but Manchester United have already suffered one setback, with Geovany Quenda opting for a move to Chelsea rather than Old Trafford.
United held a firm interest in the 17-year-old who had shot to prominence at Sporting under Ruben Amorim. The head coach was keen on a reunion with one of the hottest prospects in the game and United had been monitoring the teenager even before appointing Amorim.
Quenda looked a natural fit for the right wing-back role at United after playing 18 games for Amorim in his breakthrough year at Sporting, but a deal that looked to have a lot going for it is now off. The confirmation of Quenda's summer move to Chelsea took plenty of United supporters by surprise.
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It has been claimed that the player preferred a move to London because he saw his future as a winger rather than a wingback. Since Amorim's departure from Sporting, he has returned to a role on the wing.
There probably isn't a great deal of difference between the positions, and Amorim has referred to his wing-backs as "wingers" during his time at United, but having landed one specialist in the winter, it might well be back to the drawing board for another this summer.
Patrick Dorgu has looked a shrewd addition for an initial £25million from Lecce. He has added the kind of attacking impetus on the left that Diogo Dalot and Noussair Mazraoui were struggling to provide. Dorgu will also allow Dalot to play on the right, a position he looks more comfortable in.
Mazraoui has looked like a stand-in wing-back at best, and questions persist over Dalot, who has had a difficult season swapping flanks. The pursuit of Quenda suggested Amorim wanted a more attacking option for that position and that is likely to remain the case.
Amad started his journey under Amorim as a right wing-back and offered the kind of incision that the Portuguese head coach wanted from those roles. However, he had shifted to a No. 10 position before sustaining the injury likely to rule him out for the rest of the season.
He offered the kind of attacking threat we have started to see from Dorgu down the left, and Amorim wants his wing-backs to offer more in the final third. When Dalot and Mazraoui started in those roles, they were too easily pushed into a back five.
Quenda might have been the perfect candidate for that right-sided role. Amorim wants flexibility with his players and has mentioned playing wing-backs on their 'wrong' side. Quenda is a left-footer who plays on the right and could also operate in one of the No. 10 roles.
Instead, he will do all of that for Chelsea next season. United will need to be in the market for another wing-back this summer. Mazraoui could be used more regularly as a centre-back with Victor Lindelof and Jonny Evans set to leave. Luke Shaw's fitness issues have prevented him from contributing, and Tyrell Malacia is set to leave on a permanent deal.
Amorim will want another option on the right, and having lost out on a deal for Quenda, he will have to go back to the drawing board. Not many teams operate with a back three, so there isn't a big market for wing-backs, but the United boss knows the characteristics he wants from that role.
He will hope United's reshaped football department can find someone who fits that criteria. The January deal for Dorgu is shaping up to be a success, but now they need to repeat that on the right, and the top target has already decided his future lies elsewhere.