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Other valid and antiquated instances of this loop-hole: marry great-granddaughter/-son.
That's covered in the article (tl;dr: explicitly not allowed).
Where?
"How about a grandfather marrying a granddaughter? That’s prevented here in Massachusetts by MGL Ch. 207" and it goes on to list details.
But it doesn't include great-granddaughter.
Sigh. Too many greats (and hyphens). Thanks for the correction.
I don't see "great" anywhere (as verified by a search) and I don't see anything that would amount to it ("daughter of grand-daughter" or similar, but that is harder to verify by search).
I feel like it's implied, but indeed I see that I mis-read the question. Given that newborns likely can't get married, I'm not sure how likely it is. It does occur to me, given a time machine, a lot of laws would have loopholes. ;-)
If every generation of a family marries and has kids as soon as marriage is legally permitted (15 in some states, if memory serves), one can theoretically be 60 when their great-grandchild becomes eligible for marriage. Unlikely, but certainly possible.
as far as i heard, Immigration, before issuing the marriage-based Green Card, may grill very seriously (various pretty intimate details, etc...) trying to determine whether the marriage is real. Don't think that IRS would do less when it comes to (multi)millions.

For example: http://marriage-and-immigrationlaw.blogspot.com/2007/09/must...

While this is an interesting side-effect of the expanding legal status of marriage, to my knowledge this 'wealth-passing' matter has been mostly solved by savvy accountants and tax attorneys. Dynasty Trusts generally provide a satisfactory mechanism for bypassing the GST.

See: http://en.wikipedia.org/wiki/Dynasty_trust

This article begs the question: Would entering into a marriage to evade GST be against any specific law(s)?
Lol yeah Jeremy Irons was the first person I heard to figure this out, Stephen Colbert did some HILARIOUS bits on this past year