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Carty Free grades Tottenham Hotspur’s 2021 transfer window

It was a long, weird summer. How did Spurs do overall?

Tottenham Hotspur v Manchester City - Premier League - Tottenham Hotspur Stadium Photo by Nick Potts/PA Images via Getty Images

Tottenham Hotspur’s summer transfer window has finally closed after a long, torturous summer that included a (contractually required) SAGA and ended with new faces arriving and some familiar ones leaving.

Tottenham’s summer business resulted in five additions: Pierluigi Gollini, Cuti Romero, Pape Matar Sarr (on loan at Metz), Bryan Gil, and Emerson Royal. A bunch of players also left, including Toby Alderweireld, Moussa Sissoko, Erik Lamela, Serge Aurier, and Juan Foyth.

Now that the dust has started to settle on a somewhat subdued (by Tottenham standards) deadline day, it’s worth taking a look at Spurs’ overall business and analyzing it. It was a weird summer after an even weirder year, with COVID finances dominating things and casting a shadow over incomings and outgoings. The market was strange, and it led to some deals and some really incredible transfers across football.

Letter grades never feel like the best way to evaluate something as complex as a transfer window, but it’s also one of the more approachable ways to assign value to something, so that’s what we’re going to go with.

Most of the staff is currently ignoring Tottenham completely for a couple of days (fair!) but I did manage to berate a couple of staffers into giving me their opinions on the window, along with a letter grade.


Dustin George-Miller

Is it possible to be both underwhelmed and, uh, whelmed at the same time? That’s sort of how I feel. Tottenham brought in the Serie A defender of the year, a couple of very promising young midfielders, a right back, and a backup keeper, and managed to get money for Toby Alderweireld, Erik Lamela, Juan Foyth, Moussa Sissoko and even (lol) Joe Hart. They also managed to hang on to Harry Kane and Tanguy Ndombele, even if neither really wants to be here. Considering the financial climate and the ongoing prospects of COVID struggleball, this wasn’t too shabby. If we had managed to ship off any of Serge Aurier, Harry Winks, or Matt Doherty and brought in a good striker I’d be a little higher on this window. As it is, we’ve improved for the future and kicked the can down the road a bit. I’ll take it.

Grade: B

Sean Cahill

Not a bad window. I’m glad we shored up the defense with Cristian Romero and Emerson while adding Bryan Gil in attack could be a huge payoff down the road. Pape Sarr for the future is another solid piece. I’m disappointed that we missed on some targets like Moriba, but I understand we couldn’t be free spending unless we sold Harry Kane. I would have liked to shed more deadwood in the squad but getting actual money for Moussa Sissoko and Joe Hart is not something I expected. All in all, it’s a fine window where I’m eager to see the guys we brought in but wishing we had done a bit more.

Grade: B-

Pardeep Cattry

Tottenham clearly approached the market with a pair of decent ideas, buy young players with some upside and get rid of players who won’t play much this season, but end the window with mixed marks for execution. No two incomings embody the first idea more than Bryan Gil and Pape Matar Sarr, but they, alongside Pierluigi Gollini, also spotlight a problem of the idea: prioritizing players for later is only so helpful for a team that also needs players to make an impact right away. Cristian Romero and Emerson Royal are the incomings in prime position to do so, showing the powers that be appropriately prioritized bolstering the defense. It’s something, but definitely not enough for a Spurs team that for years has been desperate for a complete squad rethink.

The real victory for Spurs is the club’s execution on the second idea. The gutting of the squad is clearly not complete, and a few positions could still use the upgrade. Still, sending players like Moussa Sissoko and Serge Aurier off is an important part of any roster reshuffle, and it was definitely a productive few months in that department.

Grade: C


Obviously, we’d love to know your opinion as well. What did you think of the window? How would to rate it? Would you even bother assigning it a letter grade, and if so, what would it be? Have your say in the comments.