Roman Abramovich’s decision to buy Chelsea Football Club has created a platform for the Blues to have legitimate dynastic aspirations.
With the exception of signing Petr Čech and Ashley Cole, the large majority of Abramovich’s transfer dealings have been economically inefficient.
For a self-made billionaire, he bizarrely screws himself over by consistently giving in to hard-line transfer negotiation tactics from opposing clubs.
The Claude Makélélé deal epitomises this thought. Real Madrid president Florentino Pérez wanted the Frenchman out and Makélélé didn’t want to stay at a club that devalued his services. How on earth did his transfer fee inflate to £16.8 million? Real’s loss was Chelsea’s gain because Makélélé was superb throughout his tenure with the Blues—hence why he won’t be on the list.
So, what are the prerequisites for a big transfer miss? It has to be a player that didn't live up to an inflated transfer fee.
With regards to why Adrian Mutu isn’t on the list, José Mourinho suspected the Romanian was on cocaine, but there wasn’t any concrete evidence to conclude that Mutu was an addict.
The Blues were right to take a risk on him because he was one of the most naturally gifted footballers in the world.
Mateja Kežman was disappointing during his spell with Chelsea but £5 million for a forward that had scored 78 goals in his last 86 games was a bargain—that is why you can’t include Kežman as a big transfer miss.
Shaun Wright-Phillips built up a good rapport with Robbie Fowler and Nicolas Anelka during his last season with City.
Anelka, who was clearly Kevin Keegan's best player, was sold for £7 million, whilst Wright-Phillips went for tripled that amount.
Maxi Rodríguez, Espanyol's magician, was available for a fraction of the fee Roman Abramovich dished out for Wright-Phillips.
If you didn't follow Wright-Phillips at Chelsea, think Stewart Downing at Liverpool.
When Wright-Phillips struggled, he received so much criticism, most of it warranted because his finishing was downright awful.
Yuri Zhirkov wasn't an elite left-back because his defending was nonexistent, yet he wasn't anything special as a winger or a left-sided forward.
He's the type of player that is signed for £1.8 million and becomes a useful squad player.
Paying £18 million for Zhirkov's services is absurd.
Signed from Benfica for £21 million
Was David Luiz even that good for Benfica? Just a caveat: I didn't watch him week in, week out, so I can't answer that question. But, I did watch him enough to concluded that his defending was dreadful.
In the infamous 5-0 drubbing to Porto, Jorge Jesus made one of the biggest managerial gaffes in recent memory, by throwing Luiz to the wolves at left-back.
The wolves being Fernando Belluschi and Hulk, who teamed up to humiliate Luiz to the extent that Jesus had to protect Luiz by moving him back into his natural position of centre-back.
To be fair, Fábio Coentrão, who replaced Luiz at left-back, was also ripped to shreds.
Ironically, both Coentrão and Luiz garnered inflated transfer fees to Real Madrid and Chelsea, respectively.
Luiz was all over the place when Hapoel Tel Aviv surprisingly won 3-0.
He and Roberto were fortunate that Carlos Martins' four assists gave Benfica a big enough lead to see off Lyon, who scored three goals in the last 16 minutes.
A few weeks prior to that entertaining win over OL, Luiz had no idea what he was doing as the French side hit the woodwork three times and missed several gilt-edged opportunities.
To provide some context: Nicolas Gaitán was sent off before half-time and Claude Puel's side were just a class above Benfica.
Somehow, someway, Benfica manage to stretch Luiz's transfer fee to £21 million.
Unsurprisingly, the same defensive deficiencies he showed at Benfica has reared its ugly head at Chelsea.
Luiz has all the tools to be a world-class box-to-box midfielder but he'll never come good as a centre-back.
Andriy Shevchenko was caught in between a cold war with José Mourinho and Roman Abramovich.
Abramovich loved Shevchenko but Mourinho didn't. The Special One treated Shevchenko with disdain and damaged the Ukrainian psychologically.
Case in point, when Mourinho went out of his way to emphasise that Shevchenko wasn't good enough to earn the status as an "untouchable."
That's £30.8 million down the drain.
Signed from Liverpool for £50 million
Fernando Torres has become a more complete player but he's not the Liverpool Torres.
Statistically, he's excellent with four shots per goal and a healthy six goals from 12 games.
Though, with Juan Mata producing clear-cut through balls like Szabolcs Huszti, plus a world-class Eden Hazard and Oscar's class—you can't help but conclude that Chelsea's three special attacking midfielders are carrying El Niño.
How many goals would Falcao have scored?
It's wonderful to see Torres scoring goals but every game, he seems to hesitate in front of goal, either shanking his shot or not taking a shot at all.
With three special attacking midfielders behind him, it's odd that he averages a pretty low 2.9 shots per goal. There are 108 players in Europe's elite leagues that average more shots per game than the Spaniard.
It goes to show how indecisive he is. When will it cost Chelsea?
If Falcao has scored 10-plus goals more than Torres heading into the January transfer window, the Blues have to sign the Colombian.
Regarding the £50 million transfer fee, it was widely panned as one of the worst transfer deals ever at the time.
Juan Sebastián Verón, who didn't have a future at United because he couldn't adapt to the Premier League, was given a second chance by Chelsea.
Sir Alex Ferguson shouldn't have been in the power position because he was so wrong about Verón.
Remember the great manager's famous quote about the Argentine?
He [Veron] is a f___ing great player and you're all [media] f___ing idiots.
The Argentine hardly even played for Chelsea as he spent most of his time out on loan.
Signed from Porto for £16.2 million
José Bosingwa has no shame.
He is one of Chelsea's worst players and he hogged the UEFA Champions League trophy as if he played like Paolo Maldini.
Paying £16.2 million for Bosingwa, whose marauding runs masked his inability to have any positional and tactical discipline, was an unnecessary punt that backfired.
I have no idea how he made the Euro 2008 Team of the Tournament, when his defending was hit and miss.
Chelsea actually won titles in spite of Bosingwa's ineptitude.
Why didn't the Blues sign Stephan Lichtsteiner from Lille?