As he told talkSPORT, Darren Ambrose believes Tottenham should have signed Calvin Bassey prior to his move from Rangers to Ajax.
Bassey, a former Premier League player who is a Spurs fan as a child, believes the Dutch champions should invest heavily in him.
Rangers have paid 23 million for the 22-year-old defender (Sky Sports), who was a star performer during the second half of last season for the Gers.
Spurs have been quite busy this summer, including adding centre-back, Clement Lenglet, to their ranks following his loan move from Barcelona.
Ambrose believes Tottenham should have taken a risk on Bassey after watching him for a brief period last season, particularly in Europe.
I saw him in the Europa League, especially in the final against Frankfurt, and I thought he was exceptional, according to Ambrose. I think this is a fantastic signing for Ajax.
He stood out and I was, as a Spurs fan, thinking, we should go for Calvin Bassey. They (Ajax) have just sold Martinez to Manchester United, so it has freed up space.
That is a snip. For me, it's a pearl (of a signing).
CLUBS FROM THE PREMIER LEAGUE WERE KEEN ON BASSEY
Bassey was wanted by several teams in England this summer, including Brighton, Aston Villa, Arsenal, and West Ham United.
Tottenham has added, and is likely to continue to seek, another centre-back to their squad as they prepare for the Premier League season and a Champions League return.
Antonio Conte was ecstatic to welcome Djed Spence, a Nottingham Forest promotion winner and Boro defender, to the team, and this shows his willingness to enter the market for players who aren't playing in the most established leagues.
Bassey would have gone that route, given that Scotland's top-tier isn't exactly well-known for its high-quality.
The hard-hitting defender will be playing Champions League football next season, just like Spurs, and he may find himself facing the north London club.