It has now been claimed by the Dail Mail that Mauricio Pochettino asked Daniel Levy to sign him two players back in 2016 who went on to lift the Champions League trophy last season.
After mounting an unexpected title challenge in 2016, Pochettino wanted to strengthen his squad in order to go for the big prize next season.
The Mail say that he highlighted both Georginio Wijnaldum from Newcastle and Sadio Mane from Southampton as transfer targets.
However, Daniel Levy failed to follow through on these requests and both players eventually joined Liverpool.
Over the last three years, both Wijnaldum and Mane have developed into some of the best Premier League players in their positions, while also lifting the biggest prize in Europe.
Meanwhile, Pochettino went 18-months without bringing in a single signing during the latter stages of his reign, acting as a stark contrast to Jurgen Klopp at Liverpool.
How good could Spurs have been with Mane and Wijnaldum?