Tottenham chairman Daniel Levy has faced mounting criticism in the aftermath of their botched deal for Eberechi Eze, and talks for Man City winger Savinho haven't exactly been plain sailing either.
Eze ultimately chose a move to boyhood club Arsenal ahead of Spurs, despite agreeing personal terms with the latter, when Mikel Arteta's side swooped in at the last second and offered him a chance of returning to N5.
Tottenham also had a verbal agreement with Palace over the finances of a deal for Eze, but as the old saying goes - a signing is never done until all the contracts are signed.
Arsenal's dramatic late hijack leaves Thomas Frank still without a star number 10 to replace the injured James Maddison, nor does the Dane have an heir to club legend Son Heung-min out wide.
Just under two weeks ago, Tottenham entered talks for both Eze and Savinho in separate deals, prompting huge excitement among the fanbase, but there is the possibility that Frank ends up with neither.
Eze is completely off the table, but in Savinho's case, the north Londoners are not giving up, despite City blocking the deal as things stand.
Reports from Brazil earlier this week claimed that Tottenham are vowing to go all out for Savinho behind-the-scenes after losing out on Eze, and his agents are in London right now attempting to facilitate a deal (Globo Esporte).
Spurs could even submit a club-record £69 million bid for the Brazil international, but Pep Guardiola has previously insisted that he wants him at Eastlands for "many years" amid Levy's interest.
"I don’t know. If it is Tottenham in that case or another club, if any club wants a player, they should call the club like we do," Guardiola said in a press conference before City's 4-0 win over Wolves.
“I am only concerned right now that Savinho will be with us for the rest of the season and hopefully many years because at 21, with the potential he has, he is an extraordinary player.
“Otherwise, he would not have played more than 3,000 minutes last season. At the end, the desire of the players is above everything. But then they have to find an agreement with the club. If they don’t take an agreement, the player will be here."
Savinho is out injured right now, funnily enough, but an alternative to the 21-year-old could be Real Madrid star Rodrygo - if Spurs can't agree a deal for the City man.
Tottenham make approach for Rodrygo amid chance of Real Madrid loan deal
Frank and Guardiola are poised to come head-to-head this weekend, and it gives club officials a chance to hold further talks over Savinho, as widely reported elsewhere.
However, City appear to be making this very difficult, and Rodrygo's pool of suitors is running low.
The 24-year-old Brazil star, who bagged 14 goals and 11 assists in all competitions last season, has struggled for starts under new manager Xabi Alonso, and Defensa Central have claimed that Real could sanction a loan-to-buy deal as Tottenham take note.
Now, Mundo Deportivo, relayed by Sport Witness, have an update on the story - reporting that Tottenham are the only side to have approached Real over signing Rodrygo - and his potential exit remains a 'live' possibility heading into the final stretch of this summer.
Jude Bellingham called the ex-Santos star their most "underrated" and "gifted" player this year, and if a deal is there to be had, it is certainly one worth considering.
Rodrygo would be the statement signing that Tottenham are crying out for after a very testing window, and one that could seriously lift spirits around N17.