Tottenham Hotspur were confident they were going to sign Liverpool attacker Cody Gakpo in the final days of the summer transfer window,
Having landed Savinho and Omar Marmoush from Manchester City, Roberto De Zerbi wanted one more forward in his Tottenham squad, and the Dutchman was his number one target.
The talk was that once the Reds landed a replacement for the Netherlands international, they would be willing to let him leave for Spurs.
The transfer saga took another twist when it was revealed that Manchester City were actually in advanced talks with the Merseysiders over a £85m transfer, with the 27-year-old wanting to join the eight-time Premier League champions instead of Tottenham.
Of course, Gakpo ended up remaining at Anfield and the north Londoners switched their attention to Mykhailo Mudryk, who moved across London on loan with a £75m option to buy.
Tottenham were lauded for their incoming transfer business across the summer as they spent more than £300m to add 10 new players to De Zerbi's squad, but it has so far yielded just one point from nine available at the beginning of the Premier League season.
With so many players arriving, it was inevitable that there would be a number of player exits too across the summer.
Alejo Veliz
Alfie Devine
Luka Vuskovic
Will Lankshear
Manor Solomon
Ashley Phillips
Cristian Romero
Djed Spence
Dane Scarlett
Radu Dragusin
Guglielmo Vicario
Souza
Pape Matar Sarr
Kevin Danso
While a number of first-team players whose minutes would have been very limited this season left, as well as people like captain Cristian Romero, Spurs also sold a number of their promising younger players who had been tipped to breakthrough at the Tottenham Hotspur Stadium in recent years.
Tottenham Should Already Regret Lankshear Deal
One of De Zerbi's top priorities in the final days of the transfer window was to bring in a new centre-forward, to provide competition for Dominic Solanke.
Spurs ended up buying Marmoush, who can play through the middle and in a variety of attacking positions, and it was expected that Richarlison would leave after the Brazilian continually told De Zerbi throughout the summer that he wanted to leave.
The 29-year-old has since been left out of the north London outfit's Premier League squad and failed to secure a move to Turkish side Trabzonspor, or former club Everton, with the Saudi Pro League the most likely move now as their window doesn't close until October 12.
De Zerbi suggested with his comments about Richarlison after the opening day defeat to Brentford that he likes a centre-forward who can hold the ball up.
"Richarlison, also I love him, but he has to play much better than Brentford.
“In Brentford every one of us we made mistakes, and we were wrong in the game, me as the first always.
But for us, the number 10 and especially when the opponent defend man-to-man, we need the striker to keep the ball, defend the ball and give us the time to go up.
One player who does have the attributes and physical stature to do that is Will Lankshear, who Tottenham decided to sell to Championship promotion hopefuls Middlesbrough in a deal that could be worth up to £20m, including significant add-ons.
The 6ft 2in striker was in demand among a number of Championship clubs following his goalscoring exploits for Oxford United during the 2025-26 campaign, but it was Boro who ended up winning the race after meeting Spurs' valuation.
It was a decision that some Tottenham fans were against, as they believed that Lankshear had the potential to make a breakthrough in the first-team in the coming seasons, and potentially even this term.
Perhaps it was seen as money they couldn't turn down, but it is already looking as though the north London outfit may have made a mistake.
The 21-year-old has been in outstanding form for Boro so far, scoring seven goals in seven appearances for the Championship club, who sit in the automatic promotion places after five league games.
His stats are impressive too, although he is showing that some improvement is needed in terms of winning duels, which he will hope will improve as the season goes on.
We know that De Zerbi likes experienced Premier League players, but with Richarlison on his way out and still some doubts over the profiles of their other centre-forwards, Lankshear could have been a very useful option this season.
Judging by what he is producing at the Riverside Stadium so far, an initial £10m fee could prove to be a bargain for Boro, and a big mistake in the transfer market for Spurs.