To think about trusting the bugger again?

[solidgoldbrass]

I did some work for him last year on several occasions. He paid me the first few times, then stopped. Eventually, after a series of nasty emails from me he admitted he was going bankrupt, so I just wrote him off.
Quite out of the blue, a couple of weeks ago, he made a payment of half what he owes me into my bank account (unfortunately the one that's hugely overdrawn and being paid off as part of my debt management plan but that's not really his fault). He's just rung me, all full of the joys of living, promised to pay the rest of the money soon and wants to offer me more work.

WOuld I be a total mug to do it given that he has apparently quite a track record of going bust and starting again?

don't do it.

Nope, once he pays the other half off and pays you in advance in future.

Ask him to pay in advance.

Money upfront maybe??

And second half of previous debt must be paid first before you even consider it

As RFASO says.

Please don't do it,

Agree with the others - make sure you have original debt paid first, and either a higher percentage or full fee paid up, up front.

Something similar happened to DH with a client a few years ago. Client made it back into business and now happily sends good sized chunks of work DH's way.
In DH's case he required full outstanding debt paid first and then about 60% of estimate cost up front for any new jobs.

Agree with all the others - payment of outstanding first and then either all up-front or at least 50%.

If he's gone bankrupt what he is doing is illegal.

I'd give him a chance once the balance was paid. I've had problems with clients and just adjust my demands regarding upfront payment, bigger deposits etc. As MoonlightandRoses illustrates, it can work out well.

I think those that are saying not to haven't worked freelance/been self-employed. Few clients carry no problems.

RedHelen - are you thinking about the whole 'trading while insolvent' issue? As long as he's not offering work from the bust company/legal entity, but from a new or different one, then it shouldn't be a problem.

he has probably set up a new company and if its limited then technically he is not doing anything illegal (possibly using his wife or relative as a temporary director) & its very common, lots of loop holes in ltd business. Me & my hubby have a ltd company and are shocked at some of the crazy rules (all legal) that our accountant has helped us with.
I would do as others said, ask him for the rest of outstanding money and get some for the next lot of work up front. You can't really ask for it all but a % of the cash up front and the rest when work is completed. good luck.

Don't do anything until you are paid for your original work. And then 50% up-front before starting any new jobs. And only if you can afford to not be paid the other 50%. I am limiting the work I do for an extremely large corporation at the moment because it takes 4 months to get the cash out of them - I can carry x amount of debt for that time but no more. So do the sums and work out if it's money you can afford to lose or wait for.