The courts have not only released about $250 million of his money that had been locked up in a dispute over his joint venture with Watson, it has also ruled that he was wronged and ordered payment of another $50 million – with a further decision on costs yet to come.
That's a lot of money even in the world of a global shipping magnate.
How do you look at money now? I ask Glenn.
"I have to take a very quick look," he says. "It doesn't last long in my hands."
In fact, he says he doesn't really handle money much these days.
"It's a commodity. It's just like keeping the books - income and expenditure."
Glenn, who is estimated to be worth about $500m, certainly didn't grow up with wealth.
"I never inherited any money," he says. "What I have, I made."
After spending his early years in India as the child of expat British civil servants, Glenn's family moved to New Zealand 1952.
He fell into classic suburban Kiwi life and has loved this country ever since.
At Mt Roskill Grammar, says Glenn, he and his brother did well. But opportunities were limited.
Every holiday from the age of 13 he worked at George Courts – the same department store where Sir Stephen Tindall got his first taste of the retail trade.
He saved money to buy boots and a stick for hockey – a game he still loves and supports through his sponsorship of NZ Hockey.
He also bought half a bike. "My brother brought the other half," he says. "My father just didn't have the income."
In the days before student loans, that meant university wasn't an option - something that would later inspire Glenn's funding of the Auckland University Business School and a business scholarship programme.
"My father was very ill – he was in hospital, he had tuberculosis and then he got cancer of the lung. So we didn't have any money. Basically had to cash in the equity in the house, sell the car and everything.
"We lived in Mt Eden and he was in Greenlane Hospital. My mother used to walk every day from Balmoral Rd to Greenlane hospital and home. She was in her 60s. We struggled through all that."
There was no vocational guidance at school, he says.
Clearly, somewhere along the way Glenn discovered a knack for business. But he says it wasn't especially obvious back then.
He didn't much like homework, he says, but he could listen and take stuff in and got pretty good grades.
When he left school he took a job at the bank. It was considered a good career path, but when it came to the crunch, the expectation was that he would have to head to a provincial town somewhere to manage a branch.
That's when he decided it wasn't for him.
He left and worked in a range odd jobs: "a wool store, a foundry, wallboards" and saved enough money to head to England for the big OE, where he worked as a butcher and plumber, among other things.
"By the time I got back, I knew what I didn't want to," he says.
Glenn liked travelling though, and got a job with TEAL (the company which evolved into Air NZ) in the cargo division.
That was when the passion for freight and logistics started to emerge. "Nobody knew anything about air cargo then but I read everything I could get my hands on."
Ultimately, it was the application of air cargo processes to the shipping industry that gave him the edge in the freight business, he says.
That and a great deal of drive and determination to prove a point.
Glenn had a series of freight logistics jobs in Sydney and back in London, where he ended up working his way up to the top of the corporate ladder, only to see it crumble as the business was sold out from under him.
That's when he resolved to do it himself and went on to build the billion-dollar business that became known as OTS Logistics, which he sold out of in 2012.
Since then Glenn has been a regular fixture in the New Zealand media as he has dived into both philanthropic, and sometimes political, causes.
He expresses frustration that at times he has struggled to get traction with politicians and officials on ideas he thinks could improve things.
Has he ever thought about starting a political party? I ask.
"Oh bloody oath," he says enthusiastically. "But there might be blood on the streets ... politically. Because I would challenge things.
"Look at Trump," he says. "He could say things better but he's getting things done."
Glenn says he'd like to see more accountability from our politicians.
It's not that he has any particular axe to grind on the left or the right. "I just want them to do better.
"We're lacking vision. I don't think we have a had a statesman running this country for some time."
New Zealand isn't alone on that front, he says. "Funnily enough, you have to go back to women – Golda Meir, Indira Gandhi and Margaret Thatcher."
Economically there is no great secret, he says. "We have to broaden our base of products and services and we're not incapable of doing that."
It is attitude that holds us back, reckons Glenn. "Cheering the All Blacks is one thing ...cheer New Zealand.
"We punch above our weight in so many different ways. We're trusted as a nation and we should be proud of ourselves. We can do a lot more. And we can do a lot more for people in New Zealand. Those that are incapable of helping themselves."
Meanwhile, Glenn still has plenty of business plans to keep him busy - property, resorts, blockchain ...
He isn't about to slow down. "I get 12 to 15 things across my desk every week," he says. "I'm not sure what retirement means – other than pushing up daisies."
