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Grading the 2019 transfer window: A Cartilage Free Captain roundtable

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The dust has settled on the transfer window. It’s time to check in with the masthead for our thoughts.

Tottenham Hotspur Unveil New Signing Giovani Lo Celso Photo by Tottenham Hotspur FC/Tottenham Hotspur FC via Getty Images

It’s (mostly) over. The English transfer window has slammed shut, meaning Tottenham Hotspur has finalized its incoming transfers for this summer, until January. The European transfer window remains open, meaning that there’s still a chance that some players could leave the club, however.

It’s been a wild couple of days, but with the dust now starting to settle on this roller coaster of a window, we thought we’d take some time to reflect on how things went. Below, members of the masthead have evaluated the transfer window and given it a letter grade.

We’d also like to hear from you! How would you evaluate the window? What grade would you give it? Are you happy? Disappointed? Still want to fire Daniel Levy out of a cannon?

Have your say in the comments. And on behalf of the entire masthead, thanks for reading Cartilage Free Captain.


Dustin Menno

After a solid 500+ days with no transfer signings, I progressed straight through the depression and existential ennui this spring and came out the other side. After last year’s magical run to the Champions League final, it was pretty clear to me that this was going to be a monster window for Tottenham. And it was! Spurs ended up signing quite literally the two best available midfielders that they could’ve expected to go after and landed both of them. Fans may not know yet just how good Tanguy Ndombele and Giovani Lo Celso are yet, but they will, and it’ll be glorious. And don’t sleep on the signings of Ryan Sessegnon and Jack Clarke, who are super young and are potential stars of the future.

Was it a perfect window? No. There remains a glaring hole at right back, even without the sale of Kieran Trippier, and the potential departures of Christian Eriksen and Toby Alderweireld loom large, even if there’s danger of doing too much in a single window. Likewise, I’ll always wonder what Paulo Dybala might have brought to the table, even if he was a luxury signing.

However, as Voltaire said, the perfect is the enemy of the good, and this window was very, VERY good. Spurs took their greatest weakness last season — the midfield — and turned it into what could be their greatest strength and the fruits of that will be enjoyed for years to come. This is maybe the best and most fun window I’ve experienced as a Spurs fan, and yes, I’m including the Bale 7.

Grade: A+


Sean Cahill

We knew what our weakness was going into this window: The midfield. Spurs got early business done with Tanguy Ndombele, then went further on Deadline Day and nailed down Giovani Lo Celso with some brilliant accounting all around. Ryan Sessegnon as our left back of the future is a great pick up and Jack Clarke as a lottery ticket for the window is a nice piece of business. I think we’re all concerned about right back, but given the market was thin, I can give it a pass. This team is now loaded....and if Christian Eriksen re-signs somehow, it’s time to challenge for the title.

Grade: A


Kim McCauley

I’m worried about the right back situation. I won’t be happy to see Christian Eriksen leave for Real Madrid if that’s what happens. But Tottenham got one of the best prospects in England for a reasonable fee and the two absolute best midfielders they could have conceivably signed. I can’t give the window anything but an A+.

Grade: A+


Pardeep Cattry

Anything was probably an improvement on last summer, but it’s pretty clear from the business done that the decisions were smart. The team targeted (some) areas of need while also adding some much needed depth, particularly so if Christian Eriksen sticks around. With all players signed being 23 and younger, Spurs are also set up for the future, which serves as a very nice perk.

Tanguy Ndombele is the most obvious example of that strategy. The 22-year-old will easily strengthen Spurs’ midfield, making things easier for all involved, from his teammates to Mauricio Pochettino, who had to do a lot with a little last season.

Deadline day signings Giovani Lo Celso and Ryan Sessegnon will primarily add to the attack. Both, though, possess a versatility that will no doubt be useful over the course of a long, multi-tournament season.

Clarke is a great pickup, and sending him back to Leeds for at least another season looks to be a great decision for his own development.

Questions still remain about right back, which is why this can’t be considered a perfect window. However, all of the players should be more than useful this season, and in the future.

Grade: A


Jake Meador

The only scenario in which this window is not an “A” is if we’re living in a fantasy world where Spurs can spend City-level amounts of money. But that isn’t Tottenham’s situation.

To recap: We have so far brought in a decent bit of money for players who were never going to feature for us — Vincent Janssen and Josh Onomah — around £20m reportedly. We also may see Georges-Kevin Nkoudou, Christian Eriksen, and Marcus Edwards leave before the European window shuts. We sold a 28-year-old right back coming off a poor season for over £20m to Spain. That’s £40m in sales already with the potential for that number to jump up over £100m depending on what kind fees Eriksen and Edwards can attract should they leave.

In terms of incoming, we bought the two best central midfielders available in the market (or two of the three best depending on how you rate City’s new signing, Rodri). We also added two promising young players in Ryan Sessegnon and Jack Clarke.

Yes, right back is a concern. But a team with our financial constraints is almost always going to have a position or two that look like big liabilities. Given our quality in central defense and midfield, it is probable that we can manage a below-replacement level RB for a little while. There’s also the possibility that Juan Foyth will do his own version of the Eric Dier Leap, moving into a brand new position and turning out to be extremely good at it thanks to a capable surrounding cast that limits what he needs to do to succeed.

I’ve followed Tottenham since 2009. We have never had a window this strong in the time I’ve followed the club. We identified obvious future stars, bought young, and managed our expenses—all while screwing PSG in the process. This window is a huge success. All hail Daniel Levy.

Grade: A


Alex Greenberg

Some of you owe Daniel Levy an apology. Yes, Spurs waited until the very end of the window to announce their last two signings. Yes, Paulo Dybala didn’t end up joining, but Spurs accomplished what they needed to do most this summer. By signing Tanguy Ndombele and Giovani Lo Celso they have significantly reupholstered a midfield that was so thin last season. Ryan Sessegnon joins as a 19-year-old who already has a lot of experience, but still has tremendous potential, and he counts as a domestic player for registration. My only qualm is that the club may need a right back, depending on how KWP fares. Dybala joining would have been loud, but he wasn’t great last year, and he would’ve cost a ridiculous amount of money when all things were considered. Levy was willing to pay €70 million just for his transfer fee. He did pay significant sums for players who did sign. It’s tough to question his willingness to spend after all that.

Grade: A


Joel Wertheimer

Fine, I know this is cheating, but my grade recommendations are true. Spurs did an incredible job landing two of the ten best young central midfielders in the world. Maybe even five best. They saw a hole, and fixed it with aplomb. If fullbacks didn’t exist, you could argue that Spurs have the best squad in the league. But fullbacks do exist and there’s a big hole at right back right now. Christian Eriksen still looks set to walk on a free next year. This offseason was almost perfect, and maybe it will all work out at right back, but we’ll have to wait and see. Still, come next year, with Jack Clarke in and Sessegnon hopefully fullback whispered, the future is super bright.

Grade: A- (2019), A+ (2020)


Jake Meister

There are so many positives trending in Spurs direction and to be even be in the same discussion as some of Europe’s top clubs proves that the culture is changing. I believe that with Lo Celso and Ndombele we’ve bolstered our midfield to an elite level when everyone is healthy. Had Dybala signed as well it’s a firm A. I understand the concern for a right back as well but you can do a lot worse than throwing out a consistent three center backs with Jan, Toby, and Davinson with a sprinkle of Foyth and Sessegnon on the flanks.

Grade: A-


Joe Patrick

While I’m sure the entire group here at CFC is happy with the players Spurs signed—albeit maybe slightly disappointed with one or two other additions that were left on the table—that’s not what’s consuming my being at this moment. It’s the surreality of it. Spurs (!) made not just two smart signings, but two massive financial statements of intent. Obviously this was the plan: build the stadium, increase revenues, etc, etc. But despite the fact that we knew this kind of window was going to happen at some point, I’m just in dreamland to see the plan manifest here and now.

Grade: A