Within a week of the December 2 break-in at the Waiouru Army Museum, Comeskey was convinced he knew who had grabbed the medals and where they were. His mission then was to broker their return before the thieves sneaked them out of the country to broker a sale on the international art and collectables black market, where they would be worth millions.
But as national and international media shone a spotlight on the case, the two men holding the booty became increasingly nervous. Gang members were sniffing around seeking a piece of the action. And even Comeskey was getting anxious.
"I could have been scooped up and thrown into the drink," he speculated.
For 10 weeks, in endless back and forward discussions, he spent hundreds of hours talking to the men under the cloak of lawyer-client privilege. He hit the jackpot on Friday afternoon.
He had some top line conditions that all involved had already agreed to. First he would refuse to supply any legal advice about how the thieves could avoid being caught by police. And the second, crucially, was the medals had to be kept intact, undamaged and must not be taken out of New Zealand.
Comeskey says he will never forget Friday as long as he lives.
"I was so overwhelmed I was speechless. Holding the Upham medal in my hand, knowing what it signified was something else. It was better than the day my kids were born," he said.
The first breakthrough had come a month earlier when the thieves had agreed to give up one of the George Cross medals to police as "a sign of good faith" that more was to come.
In a secret exchange four weeks ago, Comeskey handed over the medal to police with an undertaking others would follow on the condition he was given space and time to keep negotiations alive.
Police had little choice but to agree to his cone of silence conditions.
In the end, they had to trust Comeskey's powers of persuasion.
After convoluted negotiations between Comeskey and the two men, which involved discussions in code for the drop-off, the remaining 95 medals were eventually delivered to his Auckland office. And there they were, laid out gallant, gleaming and safe on his polished wooden desk when the police arrived.
Comeskey says he can't reveal who the two male perpetrators are - and never will.
He doubts whether police will ever find them or discover the "ingenious" hidey hole they used to secrete them away for 10 weeks.
And he is sure the men feel guilt and remorse over what they've done.
"They're not bad guys. In fact they were quite likeable. I just think they had no idea what a furore this would cause."
Last night one of the men said through Comeskey: "I deeply regret what has happened and I apologise to the people of New Zealand."
To Comeskey, the 96 medals were precious badges of courage - New Zealand military treasures. Like many New Zealanders he was angry and disbelieving at their December theft. And he made a personal pact to find those responsible. There was no better-suited seeker. As an ex-cop and criminal lawyer, he'd built up contacts in all walks of life over 20 years in the law. Many were unsavoury characters, but they too were appalled by the heartland hijack and wanted to help.
It took him three days to locate whose hands the 96 medals, including Charles Upham's Victoria Cross and Bar, (the only double VC decoration awarded to a New Zealand combat soldier) rested in.
Early on police had launched a manhunt focusing much attention on the Waiouru area where rumours abounded of an "inside job".
British billionaire Lord Ashcroft - who owns the largest VC collection in the world - was so outraged he offered $200,000 reward for the medals' recovery. But while police were searching without a lead, Comeskey was already in touch with the two thieves, having been swiftly directed by his underworld contacts.
"I made inquiries with a lot of people within a short space of time. And let's remember New Zealand is a small country," Comeskey said.
He said the pair initially denied any involvement in the heist, but later relented after what he described as "some powerful persuasion" on his part.
"They were always confident they could keep them hidden forever. But perhaps the daunting nature of what they had achieved brought some sense of realism - probably, shock-induced. "They were aware there was international media coverage, but they really had no idea of the scale of this."
What followed was more than 100 hours of negotiations between Comeskey, some meetings face-to-face, other discussions on the phone. Most of those talks involved "thrashing out the detail" about the conditions under which the medals would be returned.
"Towards the end I thought this has become too hard. But I kept at it because of the importance of what I was trying to achieve."
Four weeks ago the men finally agreed to hand over a George Cross medal to show police they were genuine. One of the conditions, however, for the return of the other medals was that they receive a slice of the reward money.
By this stage word was filtering through to the gangs that the two men had the medals in their possession. They knew they were worth big money overseas and wanted them for themselves.
"The situation was fast getting out of hand. Things were turning pear-shaped," Comeskey said. "These guys could have tried and sold them overseas, but they didn't. They thought better of that and decided to go with what I was suggesting."
However, there were concerns that police might tail Comeskey in the hope it would lead them to the men responsible. Comeskey sought assurances from police this wouldn't happen, and told the men they "could rely on me".
"In order to recover the property, there needed to be free rein to move without the big police party pouncing. This was a case where the property was of such huge importance that the detection of the offenders had to become a secondary thing."
A plan was devised for the remaining medals to be returned on Friday with messages sent between the parties in code to ensure nothing went wrong.
There were "three false starts", but once that hiccup was over things went like clockwork, Comeskey said.
Comeskey is pleased that finally the whole drama is over.
Inquiry head Detective Senior Sergeant Chris Bensemann would not say how much of the reward had been paid, but that "an amount" would be transferred to a third party tomorrow.