Spurs sold Kyle Walker to Manchester City in 2017, and that's where the problems really began, with replacement Serge Aurier failing to really settle and impress in the Premier League on a consistent basis.
Kieran Trippier impressed up until the 2018 World Cup, but he struggled last season and was sold to Atletico Madrid, with Mauricio Pochettino deciding not to bring in a replacement in a curious move.
Kyle Walker-Peters doesn't quite look to be of the standard Spurs need, whilst Juan Foyth – primarily a centre back – has been injured this season, and is yet to really have a long-term run at right back.
In 2020, Tottenham have to solve this nightmare, most likely with a new signing whilst letting Aurier go, but their problems look even worse with a former Spurs right back impressing in the Premier League.
Pochettino sold Ryan Fredericks to Bristol City in 2015, after more than six years coming up through the Spurs ranks, though quickly joined Fulham to be back in London.
Now 26, Fredericks has developed into a fine Premier League right back, showing blistering pace to get forward to support attacks and create, as seen with his assist against Crystal Palace, whilst he's also improved defensively too.
West Ham signed Fredericks for free last year, and he would now be worth millions having proven himself as a quality Premier League player, who may well get into the Spurs side at right back at the moment.
Maybe Pochettino letting him go helped him become the player he is today, so it's hard to say the decision was a mistake, but seeing a former Spurs talent impress in the position Tottenham are having major problems has to sting – especially as it's all coming with a London rival.
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