Chelsea what ifs: John Terry converts that penalty in Moscow

The 2008 Champions League final hurt. But what if John Terry had converted that penalty and Chelsea won the Champions League four years earlier?

Chelsea won the Champions League in 2012, but many newer fans will not know how close it came in 2008. Older fans do not want to remember. On a rainy night, captain, leader, legend John Terry stepped up to take the shot that would win it. He slipped and missed. Chelsea lost the Champions League (and the Premier League that season, narrowly) to Manchester United.

In reality, Avram Grant departed the club just afterwards. Luiz Felipe Scolari came in just after and was sacked in the same season. Carlo Ancelotti brought the Blues to new heights only to be unfairly sacked for failing to match those heights again. Andre Villa-Boas was supposed to be the second coming of Jose Mourinho, but all he really did was cause issues that Roberto Di Matteo needed to solve to make Chelsea champions in Munich.

But what if Terry had not missed that penalty? What if Chelsea had won that Champions League four years earlier? How different would the club look now?

The immediate effect is Avram Grant is given the job full time. His Chelsea side may not have been the prettiest, but it did rebound from Mourinho’s early struggles to push United within two points of the title.

Chelsea makes big money splashes in the market afterwards, look to capitalize on their successes. The next season starts well for Grant, but the style of play has not improved greatly. It appears to casual observers that it is less a case of him managing the team than the team managing itself. It is working though as the Blues smack away all in front of them.

The title is close, but this time the Blues prove victorious. The cup competitions do not go as well however. Chelsea seems to struggle on one off days against their rivals. The Premier League title in 2008/2009 saves Grant, but an increasingly demanding Roman Abramovich wants more.

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He does not get it. 2009/2010 was Ancelotti’s rampant season in reality, but in this reality the team running itself finally comes to its natural conclusion: chaos. Grant is sacked before October as the Blues struggle in midtable. Ancelotti is unavailable in October in this time line as he stayed with Milan, so Chelsea turns to Guus Hiddink for (in this reality’s) the first time.

Hiddink succeeded after Scolari because he was able to let the squad do its own thing again. With Grant’s hands off approach preceding him this time, Hiddink’s calmness only makes things worse.

He lasts until February as the Blues remain marred deeper and deeper into the middle of the table. Ray Wilkins is given control until the end of the season as Chelsea misses out on the Champions League.

The Blues do not stay down long however. Carlo Ancelotti finally arrives at Chelsea, a season later than expected, and recreates the Blues into a juggernaut. Without the Champions League, the Blues romp to the title even faster than they did in reality. It continues in 2011/2012 with another Premier League title and deep cup runs, albeit no 2012 win in Munich. Chelsea has begun to integrate youth and rebuild, however, and the prospects going into Ancelotti’s third season seem great.

Next: Chelsea what ifs: The season was never delayed indefinitely

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