Any hope that Tottenham Hotspur fans might have had that last season’s injury woes would depart with Ange Postecoglou promptly disappeared during Sunday’s draw against Newcastle United in Seoul.
A day of celebration as the legendary Son Heung-min bade a tearful farewell after 10 years of service turned sour when James Maddison jarred his knee after getting his studs stuck in the turf.
Before their penultimate pre-season friendly of the summer, Tottenham faced the prospect of replacing their most high-profile attacker.
After it, plans were hastily being drawn up to source a stand-in for their second most prominent one.
“It’s most likely he has a bad injury, we need to be honest with that,” Thomas Frank said. “It’s the same knee as the previous injury.
“Of course, we don’t know the full assessment of it, so we need to see that.”
Spurs would have benefited from recruiting a creative midfielder before Maddison’s misfortune.
Acquiring one has now become an absolute necessity, especially with Dejan Kulusevski also sidelined with knee trouble of his own.
Rodrigo Bentancur, Yves Bissouma and Pape Matar Sarr all stepped up and delivered in the Europa League final, but no supporter would relish watching them line up together each week. Each are defined more by industry than invention.
Of course, had Spurs got their way (and not poked the Evangelos Marinakis hornet’s nest), they would already have a Premier League-ready No 10 primed to fill the Maddison void.
Alas, Morgan Gibbs-White has joined Rivaldo, Willian and Leandro Damiao in the folklore of failed Tottenham transfers.
Perhaps there is an obvious solution to all this. Tottenham need a silky playmaker capable of operating centrally and off the left.
Jack Grealish needs a fresh start after being frozen out by Pep Guardiola. Grealish to Spurs, who says no?
Like Gibbs-White, Grealish once almost joined Tottenham, but ultimately remained in the Midlands instead.
In 2018, with Aston Villa mired in the Championship and dire financial straits, Spurs tried lowballing them for their prized asset, offering £3m plus Josh Onomah for the then 22-year-old.
Villa held Tottenham off at arm’s length before an overnight takeover eradicated any fiscal fears in an instant, squashing any need to sell their talisman. Spurs came back with a £25m bid but Villa stood firm and Grealish stayed put. The rest is history.
Much has happened in the intervening years. Grealish led Villa to promotion and Premier League consolidation, briefly became England’s biggest pin-up since David Beckham, made a record-shattering £100m move to Manchester City, won the treble, and fell out of favour, spending this summer training alone.
Plenty of Premier League players need a move this summer, but few more than Grealish, whose stock has decreased incrementally ever since his booze-fuelled, rain-soaked, shirtless celebrations atop City’s open-top bus two years ago.
You would imagine plenty of clubs would be willing to take him off City’s hands. Napoli, who have had great success reviving Premier League cast-offs, were linked earlier in the summer. Everton and West Ham have been mooted as obvious landing spots.
There is a prevailing sense that for all the glory Grealish enjoyed in Manchester (seven winners’ medals including three Premier League titles, an FA Cup and a Champions League), his mercurial magic was dimmed in sky blue. A player renowned for his individuality moulded to conform and become part of the system.
Frank’s teams have been less synonymous with bold, daring football than his predecessor’s were, but the Dane has talked up the importance of playing in a style befitting of Spurs’ To Dare Is To Do maxim.
Grealish is far better suited to a team geared towards playing on the front foot than one set up to counter.
Whether Grealish holds the same appeal to Spurs now that he did seven years ago remains to be seen. Over the past two years, Tottenham have largely reverted to their noughties type in the transfer market by prioritising promising prospects over ready-made stars.
They deviated from that strategy to acquire Joao Palhinha on loan from Bayern Munich last week, with the tough-tackling Portuguese becoming their first 30-plus recruit in three years.
Would adding another soon-to-be thirty-something (Grealish turns 30 next month) to the squad on what would likely be a similarly pricey loan deal appeal to Spurs? City would have to make compromises for it to happen, you suspect.
Nevertheless, with the obvious exception of Villa, it is difficult to think of a better fit for Grealish than Spurs, whose motto was coined with mavericks like him in mind. It is easy to visualise Grealish in the white shirt, gliding across the Tottenham Hotspur Stadium pitch, socks slung low, shackles off.
With Son LA-bound, Spurs are lacking the sort of star power that Grealish offers. Signing a talented player with a point to prove and an England place to reclaim to fill an obvious void in the squad may not be the worst idea.