Tottenham and Jack Grealish are almost synonymous with transfer windows.
There have been plenty of transfer windows in the past where Grealish has been linked with a move to Spurs, with 2018 when he came close to making the move to north London from Aston Villa.
Tottenham were keen on signing the then 22-year-old, but missed their opportunity when haggling over the transfer fee. Spurs looked set to sign him but when the deal took too long to complete and Villa got new investment, there was no longer an opportunity.
Grealish would make the move to Manchester City three years later for a whopping £100million and he has gone on to win every piece of silverware going with the Citizens.
City boss Pep Guardiola has effectively told Grealish to find a new club, with the 29-year-old not part of the squad for the Club World Cup in the United States of America.
Speaking about his omission, Guardiola said: "He had a conversation with the club and decided the best [thing was to miss the tournament]. Jack is an exceptional player but he didn’t [play a lot this season]. We decided he has to play.
"We decided don’t come here. What happens I don’t know but if he doesn’t [leave] he is a player for Man City and he will be back."
Spurs are the favourites with the bookmakers to sign Grealish this summer as Thomas Frank looks to make his mark on the squad having replaced Ange Postecoglou at the helm.
But Grealish's past admission gives Frank something of a transfer dilemma when it comes to making a decision over signing him.
Speaking way back in 2020, Grealish said: "I love that No 10 role. I'll play anywhere, off the left or right, but that No.10 [is my favourite]."
Tottenham already have a number of options when it comes to the ten role. James Maddison wears the No.10 shirt and primarily played there under Postecoglou, with Dejan Kulusevski also impressive when playing in that role. Do Spurs really need a third option there?
Grealish admitted he could play off the left or right too, but captain Son Heung-min is the preferred choice on the left, although there are question marks over his future in N17, with the South Korean more open than ever before to leaving the club where he has spent the last ten years.
Spurs have already completed the permanent signing of Mathys Tel, following a successful loan period, with the young Frenchman also playing off the left or right, with Brennan Johnson, Richarlison, Wilson Odobert and Mikey Moore all available in those positions too. As is Kulusevski.
Having signed Tel, Grealish might not be the best use of funds, but Frank will want strength in depth to challenge on all fronts next season and Grealish is a talent.