Sheer luck, against Bahrain, helped the All Whites get to the World Cup in South Africa and good timing - in the form of a bunch of self-made professionals coming together - drove the crusade magnificently along. Herbert's greatest fortune is being the national coach in the era of Ryan Nelsen, who took control of those history-making All Whites along with his old mate Simon Elliott.
Herbert's own good management may have more to do with what has happened at the Phoenix. The club - while potentially shackled by rumours connected to the former owner Terry Serepisos - continued to make good A-League signings. There are tough, committed professionals in that lineup: Andrew Durante, Ben Sigmund, Vince Lia, Tim Brown, Manny Muscat, Chris Greenacre et al.
The quality of the Phoenix signings are impressive, especially when you consider the flotsam and jetsam that passed through the two dismal Auckland franchises. Herbert has not only discovered a player like Muscat and lured Ifill and co to Wellington, but is keeping them there.
"He knows what people are all about and gets the best out of you," Muscat has said, a sentiment that would not be repeated everywhere in New Zealand soccer. But then again, virtually no coach is universally popular, with players or those he is in contact with.
Unfortunately, the Phoenix have been seriously below par against Brisbane - a team of elegant aspirations - and now Central Coast, who tore them apart from the outset and should have won by six over a team missing Brown and Durante.
Brown is a popular everyman character whose tireless work on the field is matched by innovation off it, as when he pushed pre-match publicity for the All Whites' famous match against Bahrain, and organised - with Sigmund - a special pre-World Cup training camp in Australia.
Brown and the similarly suspended Durante, the captain, were badly missed at Gosford. But if their absence is all it takes to turn the Phoenix second-rate, then the club is jumping on thin ice. Considering the mainly poor effort at home against Brisbane, a malaise is taking hold, one that Herbert has to figure out tactically and spiritually. Either that or the Phoenix have been found out. The Phoenix skill is heavily weighted to the flanks. Paul Ifill's passing is so exceptional that even in this lacklustre performance at Bluetongue Stadium, a couple of his passes have stuck in the memory as highlights.
There are many players of Ifill's ilk around the world, but finding one who feels at home in the Wellington environment, doesn't long for higher levels and can match his skill to the surrounds is the key - and the club has struck gold in his case. Ifill's cameo style is so good that it is often the main act.
I kept looking for Leo Bertos to spark something against Central Coast but he appeared as an add-on to something that wasn't working anyway.
So the Phoenix have slumped in results, but especially performance. A bandwagon-in-waiting is inviting passengers to get off. The Phoenix must lift again.
There are players known as coach-killers, whose ability to always find career-saving performances are as inevitable as the future heartache they will cause. Herbert's teams have thrilled at international and club level - remember not only Bahrain and what followed but also that magical Phoenix finals run a couple of years ago. Yet I wonder if Herbert is a club killer, good enough only to keep the Phoenix out of the small print yet not bad enough to invite criticism in a New Zealand soccer environment still forming its expectations.
Has he raised the club above fair predictions, or is he failing to take them to the limits? Given New Zealand's erratic, mainly low-key soccer history, such judgments are very difficult to make, although in his favour for now.
And Herbert is a man of surprises, or one who has been involved in them. A somewhat remote character, he is no Harry Redknapp. Where the Spurs boss could sell an ice-making machine to Eskimos, Herbert would struggle to sell them thermal clothing - yet most of his club players are very loyal.
Yes, the riddle and and the mystery, making it doubly difficult to predict how the rest of the Phoenix's A-league season will play out.
MAGIC MOMENT
Canoe star Lisa Carrington stormed to national titles as she builds up to London Olympics.