What Taylor Swift can teach us about transfer window heartache 2 years ago

What Taylor Swift can teach us about transfer window heartache

'It's a cruel summer.'

Tell me about it sister. The summer transfer window can be a cruel maiden at the best of times, but never more so than this year. The drastic rescheduling of the footballing calendar has resulted in a concertinaed close season that will bleed into the new campaign as well as overlapping the end of the current term. Anyone hoping for less melodrama and heartache as a result of the shorter time period is sadly mistaken. If anything the usual roller coaster of emotions is only heightened. There is the same slow-burning infatuation with prospective targets, the same mixed signals and gaslighting, and the very same sense of desolation when a player you've seen photoshopped in your club colours for weeks ends up in the arms (and pristine new home kit) of another. It's a muppet movie with no happy ending.


As such, there is no one better placed to navigate us through the heartbreak and headfuckery of the transfer window than the Princess of Pop herself, Taylor Swift. That's right, she may be better known for her infectious melodies, soaring vocals and empowering lyrics, but T-Swizzle can also teach us a thing or two about negotiating fees that your heart can't pay upfront without performance-based add-ons. And nowhere does the Nashville songstress address the cruel chaos of close season contretemps more than in her 2019 masterpiece 'Cruel Summer'. On the surface it's an anthemic paean to doomed love, combining swirling synth-pop with a crushing sense of romantic fatalism. But scratch a little deeper and it says something profound about the latest transfer gossip. Here's a deep dive into why and how. And indeed whom...

'Fever dream high in the quiet of the night, you know that I caught it...'


Straight off the bat, Tay Tay is exemplifying precisely what it's like to first become obsessed with a particular target. You chance upon a rogue report on social media, or perhaps a throwaway remark on TalkSport and immediately, you're smitten. It makes so much tactical sense. Before you know it, you're including them in various formations and contemplating how they'd best fit into your team. Of course it can only end in ultimate disappointment, and you fool yourself into thinking you're not emotionally invested. But let me tell you honey, you are.

'Bad, bad boys. Shiny toy with a price. You know that I bought it...'

Delving a little deeper, Swift examines the fickleness of the modern football fan, and really, who amongst us can deny that a sobering mirror is being held up to our gluttonous fat faces. If we're being honest with ourselves, we do treat the latest talented prospects as mere objects we can haggle over and buy - a 'shiny toy with a price'. That said, such frivolous whimsy can very quickly turn into something far more sustained and real. Once we've digested all the 'stat bombs', feasted on each and every YouTube compilation, and gobbled up every long-form read on their humble beginnings, we are well and truly smitten.

'Killing me slow out the window, I'm always waiting for you to be waiting below...'


Ah, the bane of every football fan's summer - the transfer saga. As much as we're desperate for a deal to be concluded within days of the transfer window opening, these things take time. It can become a soul-destroying tale of claim, counter-claim, progress, snag, major development and frustrating standstill. The bigger the prospective signing, the longer the pantomime. It's certainly a waiting game and doesn't Taylor know it! 'Killing me slow out of the window' is self-explanatory whilst 'I'm always waiting for you to be waiting below' uses Romeo and Juliet imagery to symbolise scrolling through your timeline for that elusive 'Here we go!' announcement.

'Devils roll the dice, angels roll their eyes. What doesn't kill me makes me want you more...'

They say that 'absence makes the heart grow fonder' but the same can be said of protracted transfer talks. As much as we get frustrated by the convoluted dynamics of a full-blown summer saga, it only serves to whet the appetite further. In fact, the longer and more complicated the negotiations, the more the player seems worth it. If everything is sorted with the minimum of fuss, you start to question why no one else was interested - and why the selling club were so happy to offload. 'Devils roll the dice, angels roll their eyes' is clearly a thinly-veiled dig at Manchester United and their repeated inability to get a deal over the line.

'Oh, it's new the shape of your body, it's blue the feeling I've got. And it's ooh, whoa oh it's a cruel summer. It's cool that's what I tell 'em, no rules in breakable heaven. But ooh, whoa oh, It's a cruel summer with you...'


The chorus is as prescient as it is irresistibly catchy. With just a few infectious bars, Tayto is able to express the twisted beauty and perverse pleasure that comes from the transfer merry-go-round like perhaps only Fabrizio Romano can. 'It's new the shape of your body' is a playful reference to players returning to their clubs having enjoyed the summer break a little too much. It also points to the vital importance of having new recruits on board before pre-season training begins in earnest.

'It's blue the feeling I've got' is very clearly a nod to Chelsea and the heavy investment their squad would undertake this year. Remember the Stamford Bridge outfit were still barred from signing any new players when Swifty penned the ditty and so she was foreshadowing Roman Abramovich making up for lost time.

As much as 'Cruel Summer' is a crowd-pleasing classic of the pop-angst genre, it is of course laced throughout with the pain of ultimate heartbreak. That sense of having loved and lost. No where is this clearer than in the 'oohs', the 'ohs', and especially the soul-crushing 'whoas' of the titular lines. That's because, in this particular case, T-Bone is telling us that the summer long pursuit of her number one target has proved unsuccessful. Who knows the exact ins and outs. Perhaps the Swiftdog missed an arbitrary early August deadline, or maybe she was gazumped by Selena Gomez or something - it's hard to tell.

One thing is certain - it's over. She has no choice but to move onto other targets. Perhaps Douglas Costa on loan with an option to buy. Although clearly inconsolable about the one that got away, the Swiftmeister General is philosophical to the last, admitting that there are indeed 'no rules in breakable heaven'. Alas, the bright yellow bar of life does not shine on her. Think on that, Ed Woodward. Think. On. That.