As he told it, Villas-Boas had wanted Spurs to sign Joao Moutinho, but the Porto midfielder was way down the list of targets compiled by the club's data team - and some way behind Mousa Dembele, who came out on top statistically.
Spurs signed Dembele but did not move for Moutinho until it was too late, eventually missing out on his signature by a minute after time ran out on deadline day.
"It drained me emotionally to the point where, here was a guy that the data was not showing all that he represented from the coach's perspective. He was a player that knows your leadership, a player that knows your style, adaptability to your style," Villas-Boas said.
"We had massive, massive arguments in the beginning because of this with Moutinho. It was unfortunate, because we were going to build up a very strong midfield." Villas-Boas (right, top) was relaying the anecdote to illustrate the challenges coaches may face as data and Al play an ever-increasing role in identifying transfer targets.
Spurs, plainly, have been using data to inform recruitment decisions for well over a decade, but today they are emerging as one of the smartest English clubs in the field - and Villas-Boas's latest successor is more relaxed and confident about the practice.
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