Transfer deadline day is always liable to turn up a couple shockers, either in completed deals from out of nowhere or transfers that appear imminent only to collapse right before the crossing of the final T. Real Madrid’s failed attempted to buy David de Gea from Manchester United is one of the latter, and what a hilarious disaster it was.

Some backstory: de Gea came up through the Atlético Madrid youth system, eventually became one of the youngest and most promising starting keepers in Europe, and was then brought in by Manchester United to be their rock in goal for the next decade. Despite thriving for one of the biggest clubs in the world, it was always an open secret that Atlético’s cross-town rivals Real Madrid wanted to make the Spaniard the successor for their own homegrown legend between the sticks, Iker Casillas.

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United, believing themselves second to no one in the international soccer hierarchy, never took well to the idea that quite possibly the best keeper in the world would ditch them for a so-called “bigger” club and thus rebuffed Madrid’s advances at every stop. However, with Casillas finally and ignominiously getting forced out at Real earlier this summer, club president Florentino Pérez launched Operation: de Gea in earnest.

This set into motion a months-long cold war of sorts between the two clubs. Madrid inquired about de Gea’s availability; United scoffed; Madrid brought up the fact that de Gea had run down his contract to its final year by refusing renewal offers, making it clear that the player wanted out; United countered by saying they didn’t need the money and that this was a point of principle; de Gea himself told the club he wanted to leave; United responded to Real that if they wanted de Gea so badly, they should give over defender Sergio Ramos in an exchange deal; Ramos began flirting with United, eventually agitating for the move; Real gave Ramos the raise he was really after, taking him off the board as a bargaining chip; United stood firm, intimating that anything short of a €45 million record goalkeeper fee would be met with laughter and a “Fuck off”; and a frustrated Real started letting out that they would promise de Gea a huge signing bonus if he’d decide to stick out his final year in England and then sign with them for free next summer. As recently as a couple days ago, the two superclubs had appeared to talk themselves into a stalemate.

Then news broke yesterday. According to all reports, Madrid had brought United their first official offer: something like €20 million upfront, plus another €10 million in bonuses, and the inclusion of Keylor Navas, a stud keeper in his own right, in exchange for de Gea. It wasn’t quite the record fee United had said they wanted (depending on how you valued Navas’s inclusion), but it was a whole lot for a player who could and certainly would leave for free in a year’s time. With some qualms, United accepted.

Even at that point, the deal still had a long way to go before being finalized. For his part, Navas joined Real a couple years back last year with the expectation that he would be the club’s starting keeper. Instead, he was made the aging, confidence-shorn, increasingly despised Casillas’s backup, forced to bide his time before the man ahead of him was mercifully shipped elsewhere. Casillas’s move to Porto was supposed to be Navas’s chance to man the posts for the world’s most famous club ... until the whole de Gea chatter came about.

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For Navas, the situation was simple. He wanted either to be given the starting job at Real or else be sent someplace where he would be first choice. A starting keeper swap between Real and United looked like the best, most expedient solution for everyone involved. Because of the late stage of negotiations, United had to convince Navas to join them, agree to contractual terms, then have him pass a physical all in the span of a few hours. The two parties reached an agreement so late that there wasn’t even time to fly the Costa Rican to Manchester for one of United’s own doctors to administer the exam; one of Real’s doctors had to do so there in Madrid.

Still, as the hours wore on, the deal remained on to all outward appearances. Things got a little tighter as the clock neared Spain’s 12:00 a.m. local time deadline, but surely two sophisticated clubs could hammer out the fine print of the deal before it was too late. Then the clock struck midnight and all hell broke loose.

Immediately following the realization that somebody done fucked up, it was unclear exactly what went wrong. That didn’t stopped the rampant rumors and speculation. The first story making the rounds was that United submitted their finalized papers at 12:01 a.m. Madrid time, one minute past deadline. This and the deal’s collapse in general sparked a furor among certain heavily biased pro-Real corners of the Spanish media. A cursory look at some of the tweets from El Chiringuito TV, a popular pro-Madrid TV show, will tell you all you need to know about how this went over among Real supporters.

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(A sampling: “From the beginning Van Gaal DID NOT WANT TO TRANSFER De Gea”; “This is REVENGE by Van Gaal and United. Unitied have NOT MADE THIS EASY.”; “Those most INJURED are Keylor Navas and De Gea. United HAVE LAUGHED at them.” TELL ’EM WHY YOU MAD.)

As time wore on, however, the story got murkier. United came out saying they had proof that they had handed everything required of them over to Real in time. According to this theory, it was some sort of technological error on Real’s part—maybe an inability to open a document that was possibly password protected?—that prevented them from submitting the final documents to the La Liga offices in time for approval. For their part, La Liga officials (and the issue of timing here is that the Spanish league requires all clubs to register their players for the upcoming season with the league office before the deadline; failure to do so means the player is unable to play for the club until the next registration window in January) claimed that they didn’t receive any paperwork at all until 28 minutes after the deadline.

As of last night, it looked like the whole affair was far from over. Real were expected to present league officials either with evidence that they did in fact submit everything on time or to seek some sort of exception to allow the transfer to go through despite the delay. This morning, though, the club decided not to appeal, as La Liga rules clearly state that the deadline is the deadline and there can’t be any exceptions.

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Now, with most of the logistical insanity out of the way, we can try to parse what all of this means. First of all, it’s hard to apportion blame here. On one hand, United have to be looked at as the culpable party, since they are the ones who can afford to lose out on a relative pittance in exchange for another few months at the very least with one of the three or four best keepers on the planet. They always wanted to stick it to Madrid for trying to bully them into selling de Gea, so giving Real hope of signing him right before jamming the knife in their backs just as everything appeared finalized is a persuasive motive to dally when sending the final email.

On the other hand, they are now stuck with what one can only assume is a livid keeper who probably wants nothing to do with the club anymore. De Gea has been great for United for years now, and until this window has handled the swirling interest from Madrid very professionally. Their failure to make his dream move come true, plus the rumors that his relationship with the club had soured as of late because of broken promises and Van Gaal’s brusque management style, makes it hard to blame him if he feels United should’ve done better after all this. Of course, he can’t exactly threaten to sit out his final year with the Euro Cup on the horizon for next summer. It’s hard to imagine him ever really committing himself to the team this year, but the lure of the upcoming international tournament means he has to try—at least until January, when the transfer could theoretically be broached again.

Real obviously feel incensed. To them, blame clearly lies with United, and they said as much in a quietly seething statement today:

The key time appears to be that eight-hour span between when Real sent United the transfer paperwork and United sent back some minor corrections. It’s possible that United spent that time negotiating with Navas, but nobody knows for sure.

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Navas himself has to feel really weird about everything. It is true that in his ideal scenario, Real would never have pursued de Gea at all, leaving him standing as their number one keeper this season. From that perspective, Navas in the end winds up with what he most wanted: the Real Madrid starting job. That, though, ignores the impact of knowing that your employers desperately wanted to be rid of you, might very well hold some resentment towards you for not agreeing to contract terms earlier, and will now just sign their preferred goalkeeper either in the winter or next summer. Navas’s reprieve is temporary at best, and there’s no guarantee his next club is as good of a landing spot as United would’ve been.

The simplest takeaway from this whole debacle is that transfers are hard, especially when they involve multiple players and a tight deadline, so it’s not too much of a shock that this one managed to slide through the cracks. I think that’s a little naïve. Real might accuse United of failing to open negotiations until the start of deadline day, but that’s not a truly honest appraisal of the situation. Both clubs had been negotiating the deal for months in the media, they were both just too proud to get together and knock out a deal when there was ample time to address all the little things that inevitably come up in transfer and contract negotiations

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No, what we really saw last night was a carefully waged power struggle. United like to think of themselves as the biggest team in the world, thanks to their financial might and their history. However, their post-Alex Ferguson struggles and inability to quickly rebuild their squad back to its old heights has weakened their position in the eyes of other clubs and players themselves. De Gea’s interest in leaving, Real’s belief that de Gea was available at the right price, and United’s failure to sign any from an assortment of available superstar replacements all strike out against the club’s self image. Rather than accepting a lower spot on the totem pole, United stuck stubbornly to their principles, insisting on only doing business on their own terms (and, depending on whether you believe the conspiracy theories, maybe even sabotaged the deal intentionally as a further assertion of power).

Real Madrid (rationally) view themselves as Europe’s top dogs, able to sign quite literally anyone in the world they want. When they and a second-tier club want a player (Gareth Bale), he comes to them. When they are through with a player (Ángel Di María), they ship him out to someone smaller. And when one of Real’s inferiors wants to play games with the transfer of a player the Spaniards covet (de Gea), they insist on winning in the end, whether the other club likes it or not.

By scuppering the deal at the last minute, intentionally or not, United upset the status quo about who ultimately calls the shots. It might be strange given the teams involved, but victory for United is victory for the little guy, Pyrrhic or otherwise. We can laugh at Real’s humiliation, laugh at United’s outsized self-image, and laugh at them both over passive-aggressive battle that didn’t quite end up well for either of them; but we can definitely laugh.

All photos via Getty