Chris Liddell's new job as US Deputy Chief of Staff in the Donald Trump administration means he's in for the possibility of public humiliation and a lot of court politics, "the likes of which we haven't seen since Henry VIII in England", according to senior lecturer in international relations Van Jackson.
Dr Jackson, who is from Washington DC and lectures at Victoria University, says working for Mr Trump will be a challenge.
"Liddell's coming in to be Trump's economic man essentially, and that happens to put him at odds with most of official Washington."
Mr Trump's current crusade is what's being described as a fast-moving opioid crisis.
"If we don't get tough on the drug dealers we're wasting our time, and that toughness includes the death penalty", Mr Trump says.
Dr Jackson warns Mr Liddell's responsibilities could be wider than expected.
"Chris Liddell may expect to take on some surprising challenges."
Ivanka Trump tweeted her congratulations, saying, "In this new role you will undoubtedly continue to apply your many talents to skilfully serve our country and administration."
Speaker of the House Trevor Mallard tweeted, "Whatever we think of Donald Trump, Liddell's appointment is significant and has a chance of being important for New Zealand."
Mr Liddell was Dux of Mount Albert Grammar School in 1975, and Headmaster Patrick Drumm says he still provides scholarships for students and staff.
But is he likely to last in the job?
"Nobody lasts - maybe a few months, a year," Dr Jackson says.
Mr Liddell wouldn't comment on the appointment on Tuesday.