Rewind the clock back to the 2017/18 season and Tottenham left it very late in the summer transfer window to do any business.
Having parted with the likes of Kyle Walker, Federico Fazio and Clinton N'Jie in July, it wasn't until the final eight days of the transfer window when the club finally brought a player in through the door.
Davinson Sanchez and Paulo Gazzaniga were the first two players to sign on the dotted line, with Juan Foyth, Serge Aurier and Fernando Llorente doing likewise prior to the deadline.
Defence was always going to be an area Mauricio Pochettino targeted in the summer and he did just that with Sanchez, Foyth and Aurier all coming in.
Well, things may have panned out differently on the transfer front had Mateo Musacchio not turned the Lilywhites down.
Then starring in La Liga for Villarreal, the Argentina international opted against a move to N17 and instead elected to join AC Milan.
The 29-year-old's agent, Marcelo Lombilla, opened up on his client's future during an interview with Milan News (via Sport Witness) and recalled the battle for his signature in 2017.
Admitting that the centre-back turned down Spurs twice, Lombilla made it clear that Milan was always the club Musacchio was intent on joining.
“In December, to give you an idea, when he was playing and was at a very high level, as well as the team, at that time I was in Italy with him. I saw Mateo of the national team and Villarreal again,” he said.
“He didn’t want me to talk to two very important Spanish teams and an English team, he didn’t even want me to sit down to listen.
"He didn’t want to, the way he felt involved in Milan and how well he was doing.
"He’s fine at Milan, he’s always loved the club and he’s always wanted it.”
“In 2017 we said no to Tottenham twice, and in 30 seconds we said yes to Milan.”
