Apart from some second hand jokes and that strange look what did he do wrong? Any tax laws broken? If so prove it, if not leave him alone.
Well, in fact there has been a principle in place for some years now that if there are a series of transactions or measures taken purely for the avoidance of tax then these will not be effective. This has been confirmed in numerous court cases. It doesn't matter whether all the steps are themselves legal, HMRC is able to look at the whole.
This particular scheme, if it is what the newspapers are reporting, would not be effective in my opinion. Frankly I was pretty amazed, I thought things like this had disappeared some time ago, and HMRC have successfully challenged and shut down things working on the same principle.
In this case you have a UK resident with UK earnings routing them through I imagine a company (ie, people don't hire or pay Jimmy Carr, they hire or pay Jimmy Carr Ltd) held in an offshore trust. The company then loans Jimmy Carr the individual the money.
If so, this is in clear violation - the sole purpose of these arrangements is to avoid tax. I'm not commenting on whether this is right or wrong.
If this is all it is - basically a loan-based scheme - it will almost certainly not be effective for tax purposes. It sounds like a very simple and actually quite old idea that has been around for a long time, and I thought that HMRC had effectively squashed them.
Either there's rather more to this than the papers have reported, or else I think some people are likely to get a large tax bill.