Henry's tango with MediaWorks continued when he returned in 2014 to host the Paul Henry Show. He was eventually moved to the ambitious AM Show, which was simulcast live on TV and radio, before again leaving the company to enter a period of "semi-retirement".
Devlin said Henry played an important strategic role, not only in attracting an audience but also in defining what the brand represented.
MediaWorks put Henry on the Drive show so that he wouldn't have to compete with the morning ZB juggernaut that was Paul Holmes.
Devlin said that the plan was to attack ZB on two fronts, with Marcus Lush and Henry working together to win listeners in the afternoon.
However, when Henry left, this scheme was severely undermined.
Devlin said the changing guard made it more difficult to define exactly what RadioLive offered in a market already well serviced by established players.
"Even now, 13 years later, I still don't know what that radio station is," Devlin said.
"We were told we wanted to be somewhere between Radio National and ZB, but I think they've really struggled to decide whether they wanted to be edgy or straight-laced.
"If you're going to be edgy, you've got to be edgy all the time."
'Complete dysfunction'
Devlin said there was added complexity with RadioLive because of the efforts to integrate the TV and radio news teams across the business.
"[RadioLive] should have been called '3News' or '3News Live'. But that was never the case. So what you had instead was competing companies within a company," he said.
"There was complete dysfunction between us and the television news crew."
The difficulty in integrating disparate entities within a business isn't unique to RadioLive.
A 2003 research paper titled 'Cultural Conflict and Merger Failure: An Experimental Approach' published in Management Science explained that most corporate mergers fail due to cultural conflict and the tendency of previously disparate arms to blame each other when things go awry.
The only difference, in this case, was that the two arms were supposed to be on the same team from the beginning.
A new song and dance
MediaWorks seems to now have pulled back on the outright integration approach, with a source suggesting to the Herald this morning that the Magic Talk team will be relocating to a new office in Ponsonby.
Mark Jennings, who was the head of news at MediaWorks when RadioLive launched, told the Herald that the integration efforts have had the added negative effect of complicating a potential sale of the radio business.
"Overseas buyers appear to be looking for a nice clean radio business and don't like the complexity of a bundled radio and TV operation, especially when the TV arm is unprofitable," said Jennings, who now works as the co-editor at Newsroom.
"I think [MediaWorks CEO] Michael Anderson has come to this conclusion and has started moves to de-couple the businesses. The next sign will if he separates out the sales teams as I don't think combining them has really worked. It's a nice idea but the products are very different and the cultures are different."
Jennings also anticipated that there may be a few more changes on the horizon.
"Magic Talk will move into radio's new headquarters and it will be very much under the control of radio's boss Leon Wratt," he said.
"It will be very easy to drop the simulcast TV programmes out of Magic's format now. It is simply a flick of a switch and Magic is a pure music play."