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Published 17:24 28 Jan 2022 GMT
Updated 17:25 28 Jan 2022 GMT
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Belgian international Dembele was an important player for Mauricio Pochettino's Spurs side, but with his contract expiring at the end of the 2018-19 season, and injuries starting to take their toll, Levy chose to cash in on him six months before.
Trippier has since described the decision as 'baffling' due to the impact that the midfielder had on the team.
"For me, the big one was selling Mousa Dembele that January. I think I can speak on behalf of the players who were there," Tripper told Alan Shearer for The Athletic.
"In the dressing room, he was an unbelievable person and all the lads loved him, but on the pitch he was the kind of player who would make a couple of per cent difference. That's what wins you things.
"It baffled me that they would sell him. I know he was going to be a free [transfer] in the summer, but with the things we were challenging for, I would have kept him there and then let him go. He was the difference between winning a trophy or not."
Trippier recently completed a move to Newcastle United from Spanish giants Atletico Madrid, but he believes that he was treated unfairly before he joined Diego Simeone's side for £20m from the north London club in July 2019.
The 31-year-old is also 'annoyed' at Spurs' chairman for supposedly offering him to other clubs behind his back ahead of his departure.
He admitted it "just wasn't happening" for him at Tottenham anymore, despite him being a regular choice under then boss Pochettino.
The ex-Burnley defender explained how the Champions League final defeat to Liverpool felt like the right time to bring his Spurs career to an end, admitting that he needed to venture to a new club abroad to "clear my head a bit."
"What annoyed me… as you know, people in football speak and there are always rumours, but I know 100 per cent for a fact – and this is what I was most angry about – that two months before the end of the season, Daniel was offering me to other clubs," Trippier claimed.
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