Tottenham’s rebuild will demand hard calls, and selling five familiar names may be the first step towards leaving a chaotic season behind.
Tottenham do not need a cosmetic rebuild. They need a proper reset. After a season that drifted towards embarrassment before survival was finally secured on the last day, the club now stands at a point where sentiment cannot be allowed to lead the planning.
The arrival of Roberto De Zerbi has naturally shifted the conversation towards new signings, new ideas and a fresh identity, but this summer cannot only be about who walks through the door. It must also be about who walks out of it.
That is often the harder part. Selling players is not just about quality. It is about timing, tactical fit, injury record, market value and whether a squad is carrying too many names who no longer feel central to the next phase. Spurs have enough evidence from the last campaign to know that standing still is not an option.
A team that spent so much of the season looking fragile, imbalanced and unsure of itself cannot simply hope that better days will arrive by accident. This is why the outgoing market matters so much. Some departures would be painful, some would be unpopular, and some would feel harsh on individuals who carry talent to offer. Yet difficult summers usually demand difficult calls.
If Tottenham truly want to move from survival mode to top-four ambition, they have to be ruthless in places. Pape Matar Sarr, Cristian Romero, Richarlison, Destiny Udogie and Radu Dragusin all fit into that conversation for different reasons, and each case says something important about where Spurs are and where they want to go next.
Pape Matar Sarr
Sarr is perhaps the most debatable name on this list because he is not the sort of player supporters would instinctively push towards the exit. He carries energy, mobility and enough technical quality to suggest there is a useful midfielder in there.
Yet Tottenham are entering a summer in which usefulness may not be enough. If De Zerbi wants more authority in central areas, more control of rhythm and more certainty on the ball, then Sarr becomes a player whose role can be questioned rather than protected.
His numbers do not scream failure. He made 26 Premier League appearances last season, scoring twice and supplying four assists, which points to a midfielder who still contributed in moments even during a difficult campaign.
But that return masks a central weakness: the 23-year-old contributes in moments but seldom directs the team’s shape. In a team that was frequently short of calm and structure, Sarr functioned as a piece within the puzzle rather than one of the midfielders capable of solving it.
That is why a sale would make sense, even if it is not a straightforward one. Tottenham appear to be rethinking the entire make-up of midfield, and when a club starts chasing upgrades, younger players with decent value often become expendable.
Selling Sarr would not be a declaration that he cannot succeed elsewhere. It would simply be an acknowledgement that Spurs may now need a different type of central midfielder if they are serious about climbing back towards the top end of the table.
Cristian Romero
Romero is the biggest decision on this list because, on talent alone, he remains one of Tottenham’s strongest defenders. Even in a poor season, he still logged 23 Premier League appearances, played 1,873 minutes, scored four goals and added an assist, which underlines both his availability across much of the campaign and his influence at both ends of the pitch.
There is a reason he continues to attract attention, including from Real Madrid and Barcelona. Aggressive, front-foot defending carries value, and his style should, in theory, suit a manager who wants bravery in possession and conviction out of it.
Yet this is exactly why Spurs should at least consider cashing in now. Uncertainty around a senior player can quickly become corrosive, especially when a club is trying to rebuild with clarity. Tottenham have already moved to reshape the backline by agreeing a £52 million deal for Jan Paul van Hecke, while Andy Robertson has signed and Marcos Senesi is also on his way, giving De Zerbi fresh defensive options before the window has properly settled.
Once that groundwork settles, Romero’s case tilts: keeping him becomes the emotional choice, not the brave one. There is risk in selling him, of course. On his day, he still looks like the defender most capable of carrying authority through chaos. But timing matters in football. If the market in Spain is strong and Spurs can command a major fee while also reducing uncertainty around the squad, this may be the moment to act. Rather than waiting for his value or influence to decline, Tottenham could choose to turn a difficult season into the right point of separation.
Radu Dragusin
Dragusin’s case feels far less complicated. The signs have been there for months that he is not trusted enough, and once that impression hardens across multiple coaching changes, it becomes very difficult to reverse.
The Romanian defender never looked like a player who truly established himself during the campaign, and the lack of usage only deepened the sense that Spurs were carrying a centre-back without a clear path towards importance.
The numbers reinforce that picture. Dragusin made only nine appearances in all competitions, failed to keep a clean sheet in the league, won just 49 per cent of his duels, managed only 35 per cent in ground duels and was charged with two errors leading to goals, even if he did average 5.3 clearances per game.
Those figures reveal the inverse: limited minutes, negligible impact when deployed. They describe a player whose minutes were limited and whose impact, when called upon, did little to change the hierarchy. The transfer activity around him makes the decision even clearer.
Tottenham’s agreement for van Hecke and the arrival of Senesi strengthen a part of the squad where Dragusin already appeared peripheral. Even if Romero leaves, there is no guarantee that Dragusin suddenly becomes central to the new project. Spurs would be wiser to sell while there is still a market, take a respectable fee and move on. This is not about giving up too soon; it is about accepting what the season already seemed to reveal.
Destiny Udogie
Udogie may be the harshest inclusion here because there was a time not long ago when he looked like one of Tottenham’s most exciting long-term pieces. Under Ange Postecoglou, he carried real thrust from left-back and often gave Spurs the kind of athletic drive that changed the shape of attacks. But football changes quickly, and this past season felt like a warning rather than a blip.
He made only 20 league appearances, failed to score and registered just one assist, which tells the story of a campaign interrupted by injury and poor attacking output. Availability matters, especially in a position where intensity and repeat sprints are central to the role.
Spurs also cannot ignore how flat he looked when he did play. For a side that needed energy from wide areas, he too often appeared to be searching for rhythm rather than imposing one. This is where squad-building logic becomes important.
If Tottenham believe Micky van de Ven can cover the role in certain matches, and if they also see Djed Spence and the younger Souza as realistic options, then left-back becomes a position where change is possible rather than dangerous.
Selling Udogie would be a bold move because his ceiling still exists in theory, but Spurs cannot build next season around the memory of a previous one. They have to judge the player standing in front of them now. On that basis, a sale and an upgrade would be a defensible call.
Richarlison
Richarlison is the easiest player to understand emotionally because he carries a habit of producing moments that pull supporters back in. He fights, he competes and he can score timely goals when the pressure is highest. In a survival run-in, those traits matter. But this should be a summer for cold assessment, not emotional accounting, and the broader picture still suggests Tottenham would be right to move on.
On paper, his league return looks respectable. Richarlison made 32 appearances, scored 11 goals and added four assists, finishing as Tottenham’s top league scorer in a team that ended the season 17th. That output means he cannot simply be dismissed as a failure.
At the same time, those numbers also capture the central frustration of his spell in North London: decent production without true command. Even when he contributes, he rarely leaves the feeling that the attack belongs to him.
That matters because Spurs need a clearer attacking order now. Dominic Solanke must be allowed to own the number nine role, Mathys Tel needs room to grow centrally, and the club should still be looking for another forward option to improve the depth and raise the ceiling.
In that context, Richarlison starts to look less like a solution and more like a player whose best value may now be in the market. If Everton or another suitor comes forward with the right offer, Tottenham should take it. Sometimes the right sale is not about getting rid of a bad player. It is about making space for a cleaner future.
