In total, during spells in charge of Chelsea, Manchester United and Tottenham Hotspur, Jose Mourinho won 217 games in the Premier League.
Mourinho won three league titles with Chelsea, something he was unable to repeat at Man United and Tottenham, two clubs who are currently a long way off of that level of glory.
In terms of the most expensive signings of Mourinho’s managerial career, even encompassing his time abroad, all four were at Old Trafford.
Paul Pogba, Romelu Lukaku, Fred and Nemanja Matic are the top four in that order, names who don’t feature in Mourinho’s top five worst signings despite their mixed success.
5. Baba Rahman – £20m
Left-back Baba Rahman arrived to replace Filipe Luis at Stamford Bridge for in excess of £20m in 2016 – Chelsea’s latest attempt to find a replacement for Ashley Cole.
Chelsea spent a sizable chunk on the Ghana international who only went on to play for the club 23 times despite being on their books until 2023.
Rahman went out on loan several times to the likes of FC Schalke, Stade Reims, RCD Mallorca and even Reading in the Championship.
Now 30-years-old, Rahman is playing his football for PAOK Salonika in Greece.
4. Juan Cuadrado – £27m
Colombian winger Juan Cuadrado was arguably joining Chelsea at the peak of his career in 2015.
Chelsea parted with £27m for Fiorentina star who was unable to replicate any of that form under Mourinho.
After just 15 appearances in blue, Cuadrado was loaned back to Juventus in the Serie A before leaving the club permanently in 2017.
Now 36-years-old, Cuadrado is still going in Italy, recently making the switch from Inter Milan to Atalanta where he’s playing alongside another former Chelsea great, Mario Pasalic.
3. Mateja Kezman – £5m
Admittedly, the £5m Chelsea paid to sign Kezman from PSV Eindhoven was a bigger deal back in 2004.
Kezman arrived at Stamford Bridge amid a lot of excitement, after all, he had just scored 31 goals in 29 Eredivisie appearances the campaign before.
However, Mourinho failed to get a tune out of the Serbian who was even handed the number nine shirt recently vacated by Jimmy Floyd Hasselbaink.
Kezman scored just seven goals in 41 appearances and was soon moved on to Atletico Madrid, where he didn’t do much better.
2. Andriy Shevchenko – £30m
It was something of a ‘stop and stare’ moment when Chelsea secured the £30m signing of Andriy Shevchenko in 2006.
The Ukraine international was truly a world-class talent, he had just won the Ballon d’Or in 2004.
However, Shevchenko’s time at Stamford Bridge felt incredibly forced and his 22 goals in 77 games somewhat tarnished his reputation as one of the best ever.
In fairness to Mourinho, Shevchenko was thought to be more of a Roman Abramovich signing, but the Chelsea boss still failed to get a tune out of one of Europe’s best strikers.
1. Alexis Sanchez – Swap deal
The only player who didn’t join Chelsea on the list – Mourinho saved a real rotter of a signing for his time at Old Trafford.
In 2018, Alexis Sanchez left Arsenal during the prime of his career – he was doing incredible things at the Emirates Stadium.
Man United fans were laughing when they effectively swapped Henrikh Mkhitaryan for the Chile international, who was handed a £350k-a-week contract.
However, almost from day one, Sanchez looked like a shadow of the player we saw at Arsenal whilst wearing a United shirt.
For Arsenal, Sanchez scored 80 goals and provided 44 assists in 166 appearances.
Yet, under Mourinho at United, the forward only managed five goals and nine assists in 45 games before being offloaded to Inter Milan.
