This man led the English club charge on the Champions League
English football received something of a bloodied nose with all three clubs bowing out of the Champions League in the last 16.
For the second time in three years no English team will compete in the quarter-finals of Europe's elite club competition.
It is a blow to the Premier League's reputation and certainly poses serious questions for anyone holding the belief that our top flight is the best league in the world.
We examine some of the factors behind this latest failure and the consequences for English football, coming as it does just six years on from the Premier League having three of the four Champions League semi-finalists.
For the Premier League's big guns, this latest season of failure means they are further than ever away from being on the level of Europe's big guns.
Real Madrid, Barcelona and Bayern Munich operate on a scale that is out of reach for the top English clubs. Their respective records in the Champions League are confirmation of that.
The Spanish giants have won the trophy three times between them since 2009. Real have been in the semi-finals for four consecutive seasons, Barcelona in five of the last six seasons.
They are ultra-consistent at this elite level and simply do not implode in the same manner their English counterparts do.
Bayern have played in three of the last five finals, winning once, and made it into the semi-finals four times in five seasons.
It makes sorry reading for England's top clubs, who between them can muster just one semi-final appearance in the last four years.
As with almost every sport at the top level, success tends to come in cycles.
Manchester United's win in Barcelona in 1999 marked the end of a long period of underachievement for English teams, stemming all the way back to the late 1980s and the total ban on English participation in Europe.
Sir Alex Ferguson made it his goal to put English football back on the map and that unforgettable success against Bayern did just that.
Although it would take a little while longer for the English 'Golden Era' to kick in, the late goals from Teddy Sheringham and Ole Gunnar Solskjaer in the Nou Camp were the catalyst.
Six years later, Liverpool raised the bar in terms of the unlikely fightback, defying the odds to overcome AC Milan in Istanbul.
Over the next four years, Premier League clubs would account for five of the eight teams contesting the Champions League final.
It was unparalleled glory but it now already seems a distant and glorious past.
The decline for English football, much like the ascent, has its roots in former Manchester United boss Ferguson.
The great Scot turned the Red Devils into a genuine continental force. Over a 17-year period, Fergie's Red Devils missed out on the Champions League quarter-finals just five times. It was a stunningly consistent era, unmatched by any English club.
They reached the semi-finals seven times and made four finals, adding victory in Moscow in 2008 to their Catalan success nine years earlier.
When Ferguson departed, United's place amongst the elite went with him.
It did not happen instantly, but this season for the first time since 1995/96 Manchester United are not at Europe's top table - they didn't even make it for the after-party in the Europa League.
During England's dominant era, United were the one true constant. Without them, things are falling apart.
As a club, Manchester City have failed to get to grips with European football. Too long on the outside looking in, the Citizens have yet to make any lasting impact.
We can of course recall United's early struggles under Fergie and allow them a degree of wiggle room, but this City squad has been assembled at great cost, includes many world-class players and, by now, should be doing much better.
For Arsenal, there is also a sense of underachievement.
The Gunners have a proud record of appearances in the group stage of the Champions League but for all that it is admirable, Arsene Wenger's team have only once threatened to win.
Their defeat to Barcelona in Paris in 2006 is effectively a blot on an otherwise underwhelming copybook, meaning if anything we should not be surprised at their failure against Monaco.
For all his domestic success, Wenger seems unable to pick his way through the knockout stages of the Champions League and perhaps that is the lesson Arsenal need to learn more than any other as they ponder their 20-year association with Wenger this summer.
Mourinho's failure with Chelsea this season was much more unexpected.
The Portuguese 'wrote the book' on this competition and he looked to have Chelsea well placed to go deep into the knockout stage this time around.
Where the others have unsurprisingly come up short, Chelsea have undoubtedly missed a trick this year.
With both Real and Barcelona looking fallible, the Blues had a big chance to make an impact and blew it - seemingly owing to complacency against a Paris Saint-Germain team they had on the rack.
Liverpool are now being forced to find their feet amongst this calibre of opposition again and that will take time, although like everything else Brendan Rodgers is doing, there is a feeling he can bring about improvement.
The prospects of an English winner in the near future appear to rest entirely in Chelsea's hands.
Luckily for Premier League clubs, the monopoly on qualification places is not under threat with England's co-efficient still ranked second in the all-important UEFA listing.
That means the ongoing battle for places in the top four each season will go on as intensely as we have become accustomed to.
The lure of this competition has not diminished for English clubs - no surprise given the financial rewards on offer.
Results have suffered, however.
The presence of two Ligue 1 clubs in the last eight - both at the expense of English opponents - must be a warning shot that is heeded by Premier League clubs.
Gone are the days when England's representatives will routinely make the last eight, semi-finals and final of this competition.
A re-drawing of the boundaries means Premier League teams are back to where they were when Ferguson began to make his mark. They must earn the right to be considered among the greats once more.
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