Spurs began the campaign as reigning Europa League champions with genuine hopes of competing on multiple fronts, only to end up fighting to preserve their Premier League status and falling short in every domestic and European cup competition they entered.
With De Zerbi now in charge, the club has already committed more than €200million to two new midfielders this summer, and further incomings are expected to be balanced by significant outgoings.
Richarlison is among the leading candidates to leave, despite playing a key role in Tottenham's fight against relegation, scoring 11 goals in 32 appearances during the campaign.
The Brazilian has only a year left on his contract, and both player and club appear to accept that their time together is coming to an end.
As a result, Tottenham are seeking an amicable exit, and one club has already emerged with genuine interest.
Journalist Yagiz Sabuncuoglu reports that Fenerbahce are prepared to move decisively for the forward, with the Turkish club looking to make a major investment this summer and having identified the Brazilian striker as a key target.
Richarlison joined Tottenham from Everton in 2022 in a deal worth £60million, but has never fully lived up to that price tag amid persistent injury problems and inconsistent form.
Other reports in Turkey suggest an official offer has already been submitted for the forward, with Fenerbahce officials reportedly in London as talks over a move continue to develop.
Should the deal go through, Richarlison would follow the path of several Premier League players to have moved to the Turkish Super Lig in recent years, giving him regular European football that has become harder to find at Tottenham.
For Spurs, cashing in now would allow De Zerbi to continue reshaping his attacking options this summer as the club looks to move past a deeply disappointing campaign and start afresh under its new manager.