Oracle Team USA wanted him, but Team NZ landed the man who was tutoring Jimmy Spithill, the youngest skipper to win the America's Cup, and other sailors new to multi-hulls to win the America's Cup in Valencia in 2010.
The one-on-one deed of gift match against holders Alinghi was the culmination of years of court wrangling which forced a challenge on the water.
Spithill, in a video tribute to Glenn Ashby in 2010, having raced USA17, an imposing 90-ft (27.4m) trimaran, said: "I think I really speak for the whole sailing team when I say that [we wouldn't have been ready without Ashby]. Most of us did not come from a multi-hull background and he was a natural pick ... to push ourselves and go beyond our limits.
"That gave us an edge, not just on the technical side of things but on the sailing side too. If you look at the performance of the two boats, we definitely pushed harder and got quite a bit more out of our boat."
Team NZ have similar sentiments about Ashby; the chirpy Australian has become a vital part of Team NZ's senior crew and brains trust along with skipper Dean Barker and tactician Ray Davies.
In his job as the trimmer of the giant wingsail, he makes hundreds of adjustments to the 40m sail which powers the boat so efficiently.
Oracle weren't the only team that wanted Ashby but he has loved the shift to the Kiwis.
"Certainly, Team NZ has really been the team that I thought I could be involved with and make an impact in a new class of boat. They are a group of guys, experts, going into new, uncharted territory with the AC72s and I thought that would be a good challenge.
"I am very, very privileged to be with such a great group of guys and to be part of this team. They have a great culture and I enjoy being part of it.
"I have always had a strong affinity with New Zealand anyway; I have holidayed here and sailed there a lot and Auckland is only three hours away from [Australian home] Melbourne - and that's been important from a family point of view.'
Wife Melissa and small girls Holly, almost 2, and Larni, 4, have called Auckland home for three-and-a-half years now and love it, he says.
There won't be a lot of time for eyeballing anyone during the racing but, when the America's Cup match starts for real in 11 days, you fancy Ashby might keep half an eye not only on Spithill but an old mate in Oracle's Darren Bundock.
The pair won the silver medal for Australia at the 2008 Beijing Olympics in the double-handed Tornado catamaran class and have been three times world champions together. Bundock has won the world championships seven times in all, four with previous partner John Forbes.
Ashby has won more world titles than you can shake a goanna at - 14 across three catamaran classes, including his favourite, the single-handed A-Class, in which he is a seven-time world champion.
So you can see that the rivalry stakes in this 34th America's Cup are high. Professional yachting is a lot like professional football or rugby these days, with athletes crossing the tracks on a regular basis.
Ashby could not have been blamed had he chosen to stay with Oracle - he was extremely highly regarded, he had a winning background and their 21-strong team of sailors consists of seven Australians, seven New Zealanders, two Dutchmen, two Italians, one Canadian and only two Americans.
The OTUSA sailing crew is a world-class.
Chief executive Sir Russell Coutts himself, Spithill and Sir Ben Ainslie are in the vanguard of top international sailors. Rising fast is Australia's Tom Slingsby, regarded as one of the biggest talents to emerge in recent times and one of the yachting heroes at the 2012 Olympics.
But this Aussie chose New Zealand and, when the America's Cup action starts, keep an eye on Ashby. Not only does he have a key role trimming that brute wingsail, he is at the centre of what is turning out to be a close-knit and cohesive sailing team.