Cashing out Simple IRA Withholdings

[MM1976]

I've got a computer illiterate family member who knows I come here for advice that needed some advice that I didn't know the answer to. Despite all the ill-advisement against it, he is cashing out a simple IRA prematurely. On the IRA Distribution Form the company sent him when he expressed his interest in cashing it out, we figured everything out except for one part:

Under Federal Tax Withholding, there are two options:

- Check this box if you wish 10% Federal Income Tax withheld from your proceeds. If this box is not checked, no taxes will be withheld.

OR the other box says:

- Yes, withhold Federal Income Tax of _____%

So what's the best option? Basically, he doesn't want to get hurt at tax time next year even if he has to have more withheld now. He called the company and they explained that the first option is the IRS penalty if you don't put it back into another IRA within 60 days. Which yes, he's not planning to do, but wouldn't the second option be better put in his tax bracket so he doesn't owe next year?

Sorry if these are dumb questions but you guys are always helpful.