With the clock winding down on transfer deadline day in 2016, Tottenham looked set to end the window with just two new signings - Victor Wanyama and Vincent Janssen.
They had swung and missed on Georginio Wijnaldum and Sadio Mane, who visited Spurs' training ground but would sign for Liverpool instead. Mauricio Pochettino was a huge admirer of Wilfried Zaha, but Tottenham were unable to get him out of Crystal Palace. The club were in the market for a player to 'break the lines'.
That, somehow, led them to Moussa Sissoko, put up for sale by Newcastle and one of the headline members in their hall of infamy. The France international had even dived to win a penalty against Spurs in their 5-1 humiliation on the last day of the 2015/16 season, so he was far from popular with either set of fans.
Tottenham's window sprung into life with hours remaining. Georges-Kevin Nkoudou - who was meant to join in a deal alongside Michy Batshuayi about two months prior - finally signed on the dotted line. Don't open that champagne too quickly, lads.
They weren't done there. Sissoko was heading to Everton for a medical, but as the story goes, he turned his phone off and stopped replying to the Toffees once he heard Spurs were interested. By the end of the night, he had signed a five-year deal at White Hart Lane for a fee of £30m, instantly becoming the joint-most expensive player in the club's history.
And no one backed him to be a success. For the first year or so, they were right. Sissoko spent much of his time on the wing, attempting to stretch play and inject some much-needed pace into Spurs' attack. It didn't work.
Being surrounded by much better players than those at Newcastle meant Sissoko wasn't necessarily relied upon and his deficiencies as a key player weren't exposed, but he nonetheless looked out of his depth. There were times when you could see his brain shut down when on the ball, the sense of occasion overwhelm him, and he became the butt of every joke in N17.
But Spurs had committed to him with that five-year deal - he wasn't going anywhere, even if they tried their darnedest. Written off as one of the flops of the 2016/17 season, he began the following campaign on the up.
While Mousa Dembele was recovering from surgery, Sissoko had the chance to play in the centre of midfield again, battling Harry Winks for the spot next to Eric Dier.
They filled different needs for the team, and Sissoko's standout additions to the lineup were his energy and steel. He hadn't quite yet found the eye for a pass, nearly getting Nkoudou's leg snapped in a 1-0 win over Bournemouth because his straightforward pass when through on goal was woefully overhit.
Spurs fans had finally warmed to him, though. Ahead of their meetings with Real Madrid in the Champions League, they lined the capitals of Spain and England and sang 'who needs Bale when you've got Sissoko?'. Just slightly tongue-in-cheek, even if the Frenchman ran rings around Toni Kroos and Casemiro at Wembley.
When Dembele returned to the fold, Sissoko dropped out again, but was on hand to take on a similar role the following season.
Except he played as if he had been given a million of those FIFA Ultimate Team attribute boost cards. Hell, he looked so superhuman at times that he made mincemeat of Jorginho, N'Golo Kante and Mateo Kovacic (at the same time) and tried to run off a hamstring injury (on two separate occasions).
Spurs, having signed literally no one in the summer window of 2018, went into the season with a half-fit squad who were desperately tired after the World Cup. Sissoko ran until his Stan Lee-designed body couldn't take it anymore. He plugged the gaps, he carried the load, and most importantly, he bossed Ajax's midfield to ensure Spurs reached the Champions League final (just don't mention what happened next).
There were huge question marks over whether he could sustain this form. While Tottenham's squad was in need of refreshing, the club opted to hand Sissoko a bumper new four-year deal, to the bemusement of even Pochettino. At the time it looked foolish and it still does to this day, with Sissoko returning to being little more than a squad player once again.
He leaves for Watford as one of the most beloved players in the Spurs changing room, and fans will not a bad word to say about his effort, his passion for the club, or his drive to win - Newcastle supporters had warned us of the complete opposite.
Sissoko's lasting legacy is that you can't look back and marvel at the success of the Pochettino era without him. That, in some way, makes one of Spurs' strangest signings a successful one.