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Grading the window: Cartilage Free Captain evaluates Tottenham’s summer transfer business

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The window has closed. It’s time to evaluate how Spurs did.

Tottenham Hotspur New Signings Gareth Bale and Sergio Reguilon Visit the Tottenham Hotspur Stadium Photo by Tottenham Hotspur FC/Tottenham Hotspur FC via Getty Images

The window is closed. It’s time to evaluate. Tottenham Hotspur had one of their busiest transfer windows in recent memory, bringing in six senior players into the first team (nine including youth/development player), their largest transfer haul since the Bale Seven. Which is ironic considering this summer’s acquisitions includes... Gareth Bale.

It’s a good time to look at everything in the window — the incomings, the outgoings — and do a quick evaluation. We asked members of Carty Free’s masthead to review Spurs’ business and assign a letter grade to the window. For our UK and international readers, we are using the American system of A-F letter grades, including + and - grades.

Be sure and put your own grades (and reasons) in the comments!


Dustin George-Miller

There’s a lot to like with this window. Tottenham came into the season desperately needing a squad refresh and knowing there were gaping holes in the team that needed addressing. To a large extent, the club has done that — two new fullbacks, a new midfielder, a backup striker, a backup keeper, and a shiny (if slightly scuffed) Gareth Bale. Few of these signings, apart from Sergio Reguilon and Bale, are stars with huge impact potentials, but they are all hopefully effective cogs in a machine that needed working parts.

My slight concern with the window is less that Mourinho was backed, and others may touch upon Mou’s perceived willingness to accept a broader range of players, and more that there doesn’t seem to be a clear plan for the future. Tottenham spent for mostly established, peak performance players, which is fine, but I’m a touch concerned about what the club will look like going forward when stars like Harry Kane and Son Heung-Min start to lose a step. Spurs are definitely a better team now than they were in June, though, and that’s a really good start.

Grade: B+


Sean Cahill

It’s weird to go into Deadline Day and basically have business wrapped up. While Spurs missed out on adding to center back depth, I don’t think we can be upset with this window in the slightest. Daniel Levy did work and he showed why he’s still one of the best at negotiating transfer deals. Spurs got Pierre-Emile Hojbjerg for basically Kyle Walker-Peters and a few bags of potato chips before plucking Matt Doherty away from Wolves, addressing two needs for the club. Adding Joe Hart on a free transfer isn’t something I expected, but at least he was cheap? Then the window got turned upside down with that loss to Everton.

I know the nostalgia tour with Gareth Bale is what everyone wants to talk about and, if he’s healthy and good, this attack is downright terrifying. However, Sergio Reguilon is the gem in this window. We’ve already seen his quality and seeing Levy do a 180 on his general stance of buyback clauses makes me wonder if a doppelganger is actually in the Lilywhite House. Vinicius is a cromulent backup striker that can provide the cover needed for Harry Kane. I get that Skriniar was too expensive, but I would have liked to see Monster come in. All in all, I can’t be mad, though. This was a good window that I had little expectation for, given the situation.

Grade: B+


Pardeep Cattry

Under José Mourinho, Tottenham’s transfer strategy has clearly switched from prioritizing pre-peak players to thinking more in the short term. As a result, the six signings the team made were all over the place — a mix of younger and older players, automatic starters and rotation. The overall good news is that Spurs now have depth they previously didn’t, even more important in a season where fixture congestion will be less forgiving. How far that will go is another question.

The highlights of the window are without a doubt left back Sergio Reguilón and midfielder Pierre-Emile Højbjerg. Both answered dire needs to upgrade in their positions, and have already demonstrated their value in a season that’s only a few weeks old. 28 year old Matt Doherty is the most obvious example of Mourinho’s short-term mindset, and is also a very clear example of the depth Tottenham needed — he isn’t world class, but having players to rotate at right back is a plus. Carlos Vinícius and Gareth Bale remain unknowns at this point, but the club negotiated fairly low risk deals for both. There’s a well-established spirit of improvement in mind, in some cases more dramatic than others, but it makes one signing particularly puzzling. The club’s signing of Joe Hart on a free, now clearly to take the place of Paulo Gazzaniga, is a terrible execution of a fine idea — if you can make a profit on a backup goalkeeper, go for it while replacing him with an inexpensive homegrown. The problem is that Hart has not shown in the last several years an ability to be better than Gazzaniga, and while it may not come to cost Spurs this season, it makes Hugo Lloris’ fitness more vital to the team’s success.

Grade: B


Alex Greenberg

I’ll be honest, I was pretty significantly whelmed when Spurs signed Pierre-Emile Hojbjerg early in the transfer window. It was a move that we knew was happening, and thus it didn’t have a ton of spectacle associated with it. But after his performance against Manchester United, that move looks like a steal. PEH absolutely dominated the park, and showed that he has the ability to be the progressive-passing DM who Spurs have desperately needed over the last two years. Sergio Reguilon has tremendous potential, Matt Doherty seems to be inspiring Serge Aurier to play even better, and Carlos Vinicius seems like a perfectly cromulent back-up striker.

And I mean, come on…Gareth Bale is back! I know his last couple years in Madrid were “meh,” but I’m still a believer and think his ceiling for performance is pretty damn high. And even if not, the nostalgia alone will be worth it. My only issue with the window is that Tottenham is now relying on Joe Hart to be the No. 2 keeper. That could hurt us at some point. Other than that, I think we may have had the best window of any club in England.

Grade: A-


Kyle Yost

Look, maybe I am a victim of recency bias here, but I find it pretty hard to complain about a window that brought in four players that will potentially slide right into the starting XI. Even though last summer saw both Tanguy Ndombele and Giovanni Lo Celso make their way to North London, too often we are crying out for impact players during the transfer window and instead see Daniel Levy make a couple speculative buys but hesitate to open the purse strings. But against all odds, the chairman went out and made multiple moves during a time of extreme financial uncertainty, and that seemed like a pipe dream just months ago.

Players like Pierre-Emile Hojbjerg and Matt Doherty may not be superheroes, but their impact has been clear already. Combining their stability with more speculative adds such as Gareth Bale and Sergio Reguilon helps cement a squad that has talent but lacked the depth required to contend across four different competitions. With the loan of Carlos Vinicius, Tottenham now has at least two legitimate options at each position, something that has not been said for a very long time. And perhaps just as important as the window itself is what it represents: Spurs are going for it.

Grade: A-