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Published 17:22 24 Oct 2016 BST
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But when Louis van Gaal arrived, Smalling - renamed 'Mike' by the Dutchman - blossomed into one of United's most consistent performers. Sure, he was still capable of the odd silly sending off (see the ones in the Manchester derby and last season's FA Cup Final), but he looked an all round more composed player in those two years, unbeatable in the air and excellent positionally.
Now back to being called 'Chris' under Mourinho, Smalling has looked shaky again. On Sunday, he was indecisive and as much to blame as anyone in the defensive clusterfuck that led to Pedro's opener. He also made N'Golo Kante look like Lionel Messi for Chelsea's fourth goal.
If United are to be anywhere near a top four place at the end of the season, Mourinho needs to pay close attention to why Smalling isn't playing like the player he's been in the last couple of seasons - especially with Eric Bailly's injury likely to keep him out for the foreseeable future.
History shows that Mourinho has always preferred to use squads made up of two players for every position. Currently, United have several players that appear to fit in where needed instead of being masters in a specific area on the pitch.
A more streamlined squad made up of players that are designated to a specific position would benefit United enormously.
Clearly, his size makes him a real physical presence in the middle of the park but, sadly for the big Belgian, his inability to pass a ball accurately means that on too many occasions he's been completely out of his depth as a midfielder.
Sooner or later Mourinho will have to spend another £90m on an actual defensive midfielder and accept that Fellaini isn't up to the job.
In the mean time...
He's not going to be able to play every match, but as a short-term fix, Mourinho would be daft not to consider him.
While we're led to believe it's a fitness matter that's keeping him out, the addition of a fully fit and firing Mkhitaryan will add a side to United we've yet to see under Mourinho.
While most of the focus may be on the defence following the Chelsea defeat, let's not forget that they were also pretty toothless in attack. Mkhitaryan could make a big difference to this.
As much as he's a handful for defenders, perhaps it could be time to try the pace of Anthony Martial or Marcus Rashford from a more central area in the weeks ahead. A bit of variety in United's attacking approach certainly can't harm them, can it?
You can catch up on the latest episode of JOE's Football Friday Live right here...

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