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Arsenal vs. Tottenham Hotspur: Q&A with Cartilage Free Captain

We check in with the white dot in the sea of red in North London.

Tottenham Hotspur v Arsenal - Premier League Photo by Justin Setterfield/Getty Images

The North London Derby is tomorrow, in case you weren’t aware. The Arsenal. The Tottenham. For pretty much all the marbles. If Arsenal win, they clinch a Champions League place and celebrate St. Totteringham’s Day. If they draw, Arsenal need to win one of their remaining two matches (or have Spurs lose). If Spurs win, Arsenal need to beat both Newcastle away and Everton at home (again, assuming Spurs win their final two).

I checked in with my favorite Spurs supporter, Dustin George-Miller (@dustingm), Site Manger at Cartilage Free Captain (@CartilageFree), for some insight on how things stand across North London. Although “favorite Spurs supporter” is kind of like favorite vegetable — it’s good for you (to have friends who support Spurs) but how much do you really like them? I kid, of course. Dustin is a great guy, really funny, and does neat things with computer-generated A.I. with his free time (the Recurrently Generated Football League is one of my favorite things any SBNation site has ever done). Big thanks to him for taking the time to chat!

You can check out my responses to Dustin’s questions here. And you should! I had a lot to say.

As a friendly reminder, TSF has a reciprocal discipline policy with Carty Free, meaning that if you go over to their comments and do something that gets you suspended or banned, you will be suspended or banned on TSF as well, no questions asked. So don’t do that. Friendly banter is fine. Being a dick is not.


TSF: What’s the mood like on the other side of North London ahead of the NLD and as the season winds down?

Carty Free: I can’t (and won’t) speak for all Tottenham fans, of course, but my sense is that supporters are both cautiously optimistic and exceptionally fragile. It’s been quite a year. Spurs started out the campaign still reeling from the disastrous Mourinho era, farted their way into hiring Nuno Espirito Santo, sacked him after three months, and somehow lucked their way into one of the best football managers in Europe. How does that happen? That, combined with Conte’s infuriating tendency to hint at taking his ball and going home every other week has led to fans’ moods wildly swinging from elation to existential nihilism. It’s been a ride, man.

That said, I feel like most Spurs fans kind of chalked this season off as a loss when Nuno went out the door, so to even be in a situation where Conte has us competing for a Champions League place feels pretty astonishing. And under Conte, the football has, for the most part, been quite good. That said, now that we’re here, it would be pretty disappointing if we didn’t qualify, and it’s especially terrifying that our qualification mostly boils down to whether we can beat you lot. It’s not at all hyperbole to suggest that this is the most important and consequential North London Derby in… what, 10 years? 15? Rivalries are way more fun when the teams are evenly matched like this and the stakes matter. I’m nervous as hell going into the NLD, but I’m not sure I’d want it any other way.

TSF: I’m guessing the answer to this question hinges a great deal on how Spurs finish the season, but has it been a successful one for the club?

Leaving aside your premise (which is correct), I think it really depends on how you define “successful.” No trophies, crashed out of the European Conference League, Top Four Is Our Everything, etc. But taken in context, I’d say a qualified yes – this has been a successful year. If you were to tell me at the lowest point in October that Spurs would be playing good football, have clinched at least Europa League this season, and have a puncher’s chance at Champions League while playing for Antonio Conte, I’d probably have gnawed your arm off. Spurs are playing well, and things are looking pretty rosy in the medium term, so long as Tottenham can keep Conte happy and feeling supported. It sure could be worse, and until recently it was!

Now the focus turns to this summer, and it’s not at all overstating it to suggest that this could be one of the most important summer transfer windows Spurs have had in a very long time. What happens over the next two months will have a huge impact on whether next season is more successful than this one.

TSF: What’s the latest on Antonio Conte? Is he staying? Is he leaving? Which of those would you like to see?

Carty Free: I’ll be honest, the will-he-or-won’t-he game that Conte has been playing in the media over whether he’s going to stay at Spurs has been exhausting. But that’s Conte’s thing – he’s an incredible coach, but he’s also a maniac and who demands that his own incredible ambition be backed by the clubs who employ him. It’s a package deal – you get the good football and (hopefully) the trophies, and in exchange you have to put up with the constant threat that he will one day explode in a cloud of rage and pique.

That said, I don’t think he goes this summer. The tea leaves lately have indicated that he’s gotten assurances that he’ll be financially supported, and the transfer rumors I’ve seen are already of a different caliber to the kind you usually see in May. He appears to be… dare I say it… content? Seems good. The only thing I can see that would upset the apple cart is if PSG can’t get Zidane and decides to back a truck full of money to Conte’s doorstep. In that event, all bets are off, even if I don’t think Conte is a particularly good fit in Paris.

Otherwise, Conte has never stayed at any one club for longer than three years, so that seems like a reasonable expectation for the length of his tenure at Spurs. The good news is that when he invariably does leave a club, unlike Mourinho he rarely leaves a smoking crater behind him. That bodes well and suggests that he’ll leave his successor at Tottenham plenty of tools with which to continue the club’s development.

TSF: Same question about Harry Kane. Will he be at Spurs next season?

Carty Free: Unequivocal yes, he will be at Spurs next season. Harry’s big chance to leave was last summer, and he blew it. He doesn’t appear to be interested in moving abroad, and he wants to win trophies, so his list of potential clubs is already pretty miniscule. Now that City have purchased Erling Haaland, where’s he going to go? The only real option left is Manchester United, and that club is both behind Tottenham in just about every metric and also an absolute hot mess.

That said, I think his and Conte’s futures are tied together. If Conte goes, I think it’s likely that Kane will push to leave as well. But I don’t see it happening. My guess is that Conte will stay, Kane will eventually sign a short and lucrative contract, he’ll break Jimmy Greaves’ scoring record and push Shearer, will be a deserved club legend, and will eventually retire as a place kicker for the New England Patriots.

TSF: Shifting focus to the NLD, where do you think Tottenham have an edge over Arsenal?

Carty Free: This match is really going to come down to both clubs’ defenses and whether they can keep the other team’s attackers neutralized. Spurs’ back line has been rock solid over the past 3-4 matches – they should’ve beaten Liverpool at Anfield last weekend and only drew due to a freakishly deflected shot – and if they can put in that kind of a performance at home against Arsenal, I rate them against Nketiah, Saka, or whomever Arsenal can throw at them.

By contrast, Son Heung-Min is red-hot right now, and we know Harry Kane loves a good North London Derby. Dejan Kulusevski has the ability to create scoring opportunities for others from virtually nothing – he’s the Premier League assist leader since January. Spurs are ruthless on the counter and will gladly exploit any space behind the back line if offered. If Arteta sets up Arsenal to actually try and play football against Spurs, I think it plays right into Tottenham’s hands.

However, anyone who’s been paying attention should already know the best way to neutralize Tottenham. When Spurs have struggled lately, it’s been when teams have played an organized mid to low block and has tried to clog up and destabilize the midfield. Brighton and Brentford both did variations of that strategy to good effect. Arteta’s best bet would be to bunker and turn the most anticipated NLD in a decade into a grim slog-fest. If he wants to try and trade punches, I think Spurs win it, if narrowly.

TSF: [tongue in cheek] Spurs score one goal - on the break, Kane drops deep, quickly spins it for Son to run onto, and somebody puts it away. How do they keep getting away with this?!

Carty Free: Because they’re really, really, really, really, really, really good at that. Seriously. Kane-Son is one of the best attack partnerships I’ve ever seen. I swear they Vulcan mind-meld before every match.

TSF: What scares you most about Arsenal vis-a-vis Spurs? Say the Gunners win the NLD. What went wrong?

Carty Free: If Spurs lose the NLD, it’s because one of two or three things happened. Either Arsenal successfully takes the air out of the ball and forces Spurs to try and play through a bunkered defense, Spurs play well but are inexplicably wasteful in attack and have one major defensive miscue, or Arsenal score the worst goal ever off a corner via Rob Holding’s big dumb head. Defensive set pieces have been an issue for Spurs all year and that would definitely be the stupidest way to lose a home NLD.

TSF: And of course, a prediction.

Carty Free: I probably shouldn’t be optimistic about this match, it only leads to pain. But I am. I feel good about this team and the way they are playing, especially after the draw at Liverpool. That’s an incredible team and we played them toe to toe; all respect but I can’t imagine getting a tougher challenge from Arsenal. Spurs have all the motivation they need, they’re playing at home in front of a raucous crowd (did you know they’re doing tifo? They’re doing tifo!), and it’s just a massive, massive opportunity. It won’t be easy, but I believe in my team, all evidence to the contrary.

Tottenham 2-1 Arsenal.