In what form is the money now?
Is it liquid? Is it in securities that are readily marketable in Spain? Or is it tied up in some land development scheme and you must first find a buyer?
Before you can have it sent here, it must be in a form that can be wired by a bank and readily converted.

How is the money being handled at the other end? Who has it now?

I think before you can get answers to your first questions, you need answers to the more basic issues of form and circumstance.

It is sitting in a bank in Madrid. It's in Euros.

With the low cost of travel to Europe right now, they are simply using this trip an an excuse to get away for a few days.

You will need to follow official channels to move the money. Several others have suggested that trying to smuggle huge sums into the USA is a good way to run afoul the US Customs laws.
Money laundering and all that good stuff.
And beleive me, a pile of banknotes will be quite obvious on x-ray equipment.

I would get the details of the account in Spain, talk to big banks here, find out what fees it will charge, what exchange rate it will offer, and go from there. I suggest you know the spot exchange wholesale rate for that day, and negotiate from there.

If it is in liquid form in Spain, why can not some of it be left there in euro form? You can withdraw it over here with atm cards just like you can draw on your US account in Europe. There are limits of course, but larger amounts could be wired when needed.d

I am sure some kind of business trip reason could be hatched to make it a business expense.

"With the low cost of travel to Europe right now"...

??? Perhaps you mean, given that your friend has a bank account with euros to draw upon, this will make the trip cheaper than using $US or $CAN (?)

As has already been said, there is not only no need to take a trip to accomplish an international financial transfer, but any attempt to handle shipping money yourselves could have unpleasant consequences.

To paraphrase the Bible, this is a good case for rendering unto the tourists that which is the tourists', and unto the banks/tax lawyers that which is theirs - to competently and legally administer. In other words, if your friend wants to take you on a trip, or even if you just want to accompany him on your own dime, fine, but keep the two goals completely separate.

Winnipeg: That is a serious amount of money. Unless your friend has an immeidate need for the money, PLEASE STOP TAKING ADVICE FROM PEOPLE ON THIS SITE (INCLUDING ME) AND GET SOME PROFESSIONAL ADVICE.

Buy your friend some books on money and investing, and tell him to take his time before he decides to do anything.

Cicerone,

You're right. I simply started this post wondering if anyone knew of any benefit to using a half baked way to exchange the money.

In Oct 2002, while in Germany someone had told me that it is possible to make out better by using some exchange system. Just thought someone might have known something.

Anyway, thanks for all the input.

OK, one more question. What's this person going to do with this amount of money once it gets over here to the US? If he is using the services of a good trust department, bank, or stock broker, for example, I would think any of those people would be happy to arrange all the details of the transfer for a very small fee -- or perhaps no fee at all if they are the ones who will be "investing" or "managing" it for him. A good way to get great advice for free or for a very worthwhile fee as opposed to the wild rantings of us here. If he's trying to beat the "system" and avoid paying anyone anything to help him or give good professional advice, I suspect he will end up like many others -- losing a great deal of it by making bad mistakes.