Following Sunday's defeat away at Sunderland, new Tottenham Hotspur boss Roberto De Zerbi might well be asking the same question as his predecessors - why, oh why, did Daniel Levy sell Harry Kane?
Losing the England skipper was perhaps an inevitability considering he had just a year left on his contract at the time, with arguably the bigger concern having been the club's plan to replace him.
Indeed, it took 12 months before a direct centre-forward successor was signed, albeit with that club-record deal for Dominic Solanke having since backfired, with the injury-hit Englishman scoring just six times across 2025/26.
As was evident again at the Stadium of Light, the 28-year-old simply can't be relied upon as Spurs' starting striker. Something needs to change.
Solanke is starting to look like another James Maddison at Spurs
For the most part, there's been no doubting Solanke's quality, with the ex-Bournemouth man arriving after netting 19 Premier League goals in his final season on the south coast.
A total record in north London of 22 goals in 62 games, almost one in three, isn't a disaster either, with the bigger concern having typically been keeping him fit and available for much of the last two years.
He certainly fits in the James Maddison category in that regard, the type of talent who could well have kicked on even further, had it not been for repeated injury setbacks.
Like Solanke, when Maddison does feature, he is a centre-piece of this side at his best, having totalled 37 goals and assists in his 75 games since signing from Leicester City.
And yet, the playmaker hasn't been seen since the days of Ange Postecoglou, while notably missing the Europa League final, proving sadly unreliable for a team in such a predicament right now.
Solanke is in that camp too, while even his return to action of late hasn't inspired a dramatic turnaround, notably registering just 18 touches of the ball at the Stadium of Light.
Considering Spurs fashioned just a solitary 'big chance' at the weekend, De Zerbi's attacking configuration was certainly not effective, ensuring a new solution could now be needed.
De Zerbi could now replace Solanke with £73m-rated Spurs star
If there was to be any positive from the loss on Wearside, it might well have been the performance of the two men on the flanks, with Randal Kolo Muani looking bright down the right.
The Frenchman came close to earning a penalty for his side in the first half, while on the opposite flank, Richarlison was his usual chaotic self, getting himself into promising openings, yet only managing to fire straight at Robin Roefs.
Having those two recognised strikers making driving runs inside from a wider role did look to be a sensible option, albeit with Solanke failing to knit things together in the centre.
With that in mind, one alteration that could please all parties would be the introduction of Xavi Simons in something of a new role as a false nine, with the Dutchman having been a surprising absence again from the starting lineup.
Also overlooked in Igor Tudor's final game in charge, the 22-year-old just hasn't found any consistency in a Spurs shirt to date, even while enjoying the highs of his brilliant brace at home to Atletico Madrid not too long ago.
Operating as a number ten that night, Simons showcased what an effective link man he can be, registering three 'key passes' in what was arguably his finest outing in north London to date.
The shift to Premier League life has been far more difficult, while finding a consistent place in the side has also been a continued problem, with the ex-RB Leipzig star flitting between a left-wing role or a number ten berth.
He may not have the physicality to operate as a lone striker, but as a false nine who drops deep to link play, Simons could well flourish, having operated in that role a handful of times during his time at PSV Eindhoven, as well as in the Paris Saint-Germain youth ranks.
Almost in a similar vein to Kane in his pomp, having Simons drawing out the centre-backs could then vacate space for the advancing Richarlison and Kolo Muani in behind, with the Netherlands star boasting the creative quality to thread the ball in behind for the pair.
Solanke, by contrast, completed only four passes last time out and lost the ball seven times from his 18 touches, hardly the mobile, progressive centre-forward that De Zerbi is likely to be in need of.