EU national resident in the Uk for 15 years - entitled to i-esa?

If an EU national has been resident in the UK for 15 years but never worked (officially) or claimed benefits what is the likliehood of them now being entitled to i-esa? EC directive 2004/38 states that after being here 5 years you get a right of permanent residence but as a ‘qualified’ person. He has not worked (legally) or been self-employed and has no family here so I don’t see how he can be deemed qualified. I initially thought we could argue that he was self-sufficient but it looks like the proviso here is that you also have to have adequate health insurance.
He is an entrenched homeless street drinker who finally claimed JSA 3 months ago. If he were to now claim i-esa would he fail the residency tests in your opinion? 

Thanks.

You caught my attention by saying “never worked legally”. What is the implication of this - was he working but illegally? If he is “old” EU (not A8/A2) then he had the right to work in this country, so he could only be working illegally if there was some illegality about the contract itself.
If however he is A8/A2 then he has been resident in this country since well before his country of origin joined the EU and that residence itself was quite possibly illegal. He can’t found any EEA rights on a period when the country of origin was not in the EEA.

As Ariadne says where the client is from may affect the matter.  If from the old EU states before 2004 then he would have the right to work and the work would be illegal only if some illegality was involved.

If they are from the A8 or A2 states then why and on what basis did they come to the UK.  i.e. did the seek asylum under ithe Immigration Act 1971 and was this granted?,  Did they come on a work visa?, etc

Thanks for your help with this everyone, it has really clarified matters for me.
With regards the matter of working ‘legally’ I now see that this is in fact a red-herring. He is from the Netherlands so any issues arising from any work he may have done would be related to possible owing tax, I would think, than a question of legality.

Thank you.

The guidance from the Commission does not sit so well with the caselaw on this issue. In W(China) v SSHD[2006] EWCA Civ 1494 the Court of Appeal said “That argument overlooks the fundamental reason for the insurance requirement that was identified as the basis of the scheme of the Directive in Chens case[2005] QB 325 to prevent the presence of the European Union citizen placing a burden on the host state. Use of free state medical services exactly creates such a burden”

This approach was followed in CH 15/09, although the claimant in that case was found to have sickness insurance through a provision in Regulation 1408/71 which allowed reimbursement of NHS costs where another member state is paying the claimant a pension. The replacement of 1408/71 by Regulation 883/04 doesn’t seem to change much, with a similarly limited number of instances where health costs can be reimbursed by another member state.

I agree with Damian- I think though that W(China) (and later Liu) definitely did not consider (at all) 1408/71 etc (as neither of the child EU nationals in those cases could have possibly been covered under that rule).

It is probably an area ripe for a reference to ECJ.