The former All Black coach reveals in his recently released book, Final Word, he nearly come to the Highlanders early in his professional career.
In 1997, the Highlanders finished dead last in the old Super 12, while Henry's Blues won a second consecutive title.
There was a feeling Auckland rugby was getting too dominant. At a meeting in Wellington, it was proposed Henry take his talents to South Dunedin.
''It was discussed by the New Zealand Rugby Union at the time,'' Henry told the Otago Daily Times recently.
''It didn't eventuate, obviously. Auckland took steps to keep me, which was nice. They put some things in front of me which I couldn't say no to.
''It would have been an interesting situation. I think I would have enjoyed it. I'd obviously had some experience of living in Dunedin.''
Henry, who studied in Dunedin and played rugby and cricket in the city, went on to coach Wales the following year, setting in motion a remarkable international career.
The Highlanders did just fine under Tony Gilbert and Peter Sloane, reaching the semifinals in 1998, 2000 and 2002, and the final in 1999, so Highlanders fans can hardly lament the coach who got away.
''I think there's a lot of what-ifs there over a period of time. To be honest, most of the what-ifs are situations you look back on and say, I'm pleased I didn't get that job.
''I don't think the Highlanders would have been one of those situations.''
Henry was a regular visitor to Highlanders country during his All Black tenure, and remains in touch in his role as a mentor to coaches.
He said Jamie Joseph had done a fine job building a competitive side through his first two seasons.
''I guess the challenge now is to try to get into the finals. A big key for the Highlanders has been to get the community behind them. I think that's starting to happen. When I used to go to Carisbrook as an All Black selector, you might be lucky to get 5000 people there.
''There's been a big turnaround. Your stadium is brilliant and your team is highly competitive.''
Henry played a major role in helping Highlanders talisman Adam Thomson blossom at international level, but he revealed assistant turned head coach Steve Hansen had been the major backer of the loose forward.
Thomson was ranked behind Jerome Kaino but now had an opportunity, even at a relatively advanced stage of his career, to make the No 6 jersey his own.
''Adam's one of the best lineout forwards in the Super 15. He's brilliant, and on opposition ball as well,'' Henry said.
''He's played some outstanding rugby for the Highlanders. Adam's challenge is to really take that step up to the next level.
''I think it's still a challenge for him. He's an outstanding Super 15 footballer. If you picked a team from all the 15 franchises, he might be your No 6.
''He hasn't really nailed international rugby the same way. I'm sure he understands that.''
