The closest Mourinho has come to an "oops" face.
According to The Guardian, Jose Mourinho is set to confirm his first signing of his second spell at Chelsea in the form of German winger Andre Schurrle. With a rumoured budget of £100 million, it is possible that the Especially Happy One could end up surpassing his transfer total from his first spell in charge at Stamford Bridge.
Some of the £225 million that he spent the first time around was good business. The £24 million fee for Didier Drogba was fully justified on May 19 2012, and Ashley Cole has shown that £5 million plus William Gallas was a far shrewder move than it initially appeared.
However, not all of that eye-watering sum went on quality players. The £30.8 million deal for Andriy Shevchenko may have been orchestrated by a higher power than Mourinho, but there were plenty of other transfers that made little to no sense. Let's take a look at the five worst signings made between 2004-07.
Quality of signing is assessed by looking at the fee paid, length of initial contract, and impact made by the player (if any.)
Jose Mourinho signed Khalid Boulahrouz from Hamburg in August 2006. The Dutchman made 19 starts in all competitions in his first, and only, season, scored no goals and committed 23 fouls. All that for around £8 million.
He was loaned to Sevilla in the 2007-08 season before being sold to Stuttgart in August 2008 at a loss. Boulahrouz's versatility allowed him to play anywhere across the back four, but his ability prevented him from doing well in any position.
Chelsea's defensive issues at the moment could lead Mourinho to look for a similar all-round player this summer. Let us hope that he makes a better buy than Boulahrouz turned out to be.
Shaun Wright-Phillips was one of the first examples of Chelsea inflation. Back in 2005 the Blues signed the nippy English winger from Manchester City for £21 million. Whilst he had showed great potential, that fee was vastly above his real value, even when the home-grown weighting is taken into account.
Wright-Phillips was not quite good enough for the first-team and was quickly consigned to the substitutes bench. He spent three years at Stamford Bridge, scoring nine goals, before moving back to Manchester City in 2008. His second spell with them revealed that he was not "the one that got away" and he was transferred to QPR in 2011, scoring for the Rs at Stamford Bridge in January 2013.
Mourinho brought Tiago from Benfica in his first summer spending spree. The Portuguese midfielder made 34 appearances for the Blues in his first and only season, scoring four goals as Chelsea secured their first Premier League title.
However, he was unable to fulfill his four-year contract as Mourinho found a better option in the summer of 2005. Michael Essien was brought in for £24.4 million, making Tiago surplus to requirements. He swapped places with the Bison, heading off to Lyon for a fee of £6.82 million.
The whole saga proved to be a waste of everyone's time, but probably made a tidy sum for Tiago's removal company.
Jiri Jarosik joined Chelsea in January 2005. A central midfielder, Jarosik was brought into a squad already boasting the talents of Claude Makelele and Frank Lampard. He made 14 Premier League appearances for the Blues and picked up a Premier League winners' medal, but it became clear very quickly that he was not going to reach the standard required by Roman Abramovich.
A successful loan spell at Birmingham City did little to change opinions at Stamford Bridge, and the Czech national was sold to Celtic in June 2006 for an undisclosed fee.
Kezman joined Chelsea from PSV Eindhoven in July 2005 for a fee of £5 million. Having scored 105 goals in 122 appearances for the Dutch club, expectations of the Serbian were sky-high. However, his seven goals in 41 appearances failed to set the Premier League alight.
Constantly in the shadow of fellow newcomer Dider Drogba, Kezman moved to Atletico Madrid in 2006 for £5.3 million. Small profit aside, this particular saga could have been worthwhile if Fernando Torres had been part of the deal with Atletico. Alas, that was a different story for a different manager in a different time.