His appointment was 'topic du jour' among senior governance circles when it was announced by MediaWorks chairman Rod McGeoch.
Weldon had a reputation for prickliness.
He could be a bit petulant.
At the NZX his leadership had been undermined by leaks during the latter part of his reign. He did not suffer fools gladly - particularly if they happened to be journalists.
But he was kind to those he respected.
And he was a business visionary and possessed of strong strategic abilities as you would expect from a McKinsey & Company alumnus.
Some members of MediaWorks' then banking syndicate were concerned the new appointment was from outside the news media industry.
But there was also support from those that felt radical changes would be the only measures to ensure the company's survival.
Unfortunately, when it came to the execution of his CEO role he ran too far and too fast for MediaWorks' strong tribal culture to absorb.
He was definitely not "one of them" - which was the fundamental point of his appointment.
This situation clearly called for deft and able chairmanship.
If Weldon has failed (and it is fair to say that irrespective of his resignation he has made many good moves) part of that failure must also be shared by the board and in particular McGeoch.
Don't get too far in front of your troops or you will get shot in the ass.
The Australian-based McGeoch did not create enough obvious public support to ensure Weldon had sufficient space to bed in change smoothly.
McGeoch has considerable charm. But he is also a very focused and imposing figure whose occasional bombast would be intimidating for some.
The situation was complicated by the position of Julie Christie on the board.
Christie is a talented player with a strong media pedigree.
But she left the news world years ago to build a reality TV empire and can be a tad dismissive of those that still hold to journalistic values.
An experienced chief executive - particularly one that has to take a company through a major business transformation at pace - would also have been aware of the management maxim: "Don't get too far in front of your troops or you will get shot in the ass."
Particularly, if those troops can easily rally support from journalists from media rivals who have been through repeated restructurings as digital disruption undermined the basis of their traditional media.
Like its rivals, the MediaWorks board was endeavouring to transform its business.
At the directors' behest, Weldon was making major changes across every level of the business: replacing the top management tier; integrating the television and radio businesses; introducing an 'audience first' focus; bumping high-priced talent that wouldn't make an accommodation over the shape of their programmes; launching NewsHub and more.
This was all survivable.
Even the non-renewal of former Campbell Live host John Campbell's contract.
But the recent axing of the prize journalistic investigative team was a step too far for the MediaWorks' journalistic tribe. Newshub host Hilary Barry's resignation was the final straw.
Companies sink or swim based on their internal culture - as former TV3 news supremo Mark Jennings and a host of former journalist stars - were quick to point out during their indulgent out-pouring of "Weldon freude" after the CEO resigned.
The former news executives and staffers have made much of their culture of giving 120 per cent. Certainly, TV3's journalistic prowess was something to be envied.
But MediaWorks is about more than its journalistic strengths.
Its prize-winning record and justifiable reputation for courageous current affairs stories was clearly central to its brand.
But the company itself was a repeat financial basket case.
It is instructive to ask whether the alignment incentives between Weldon and the board blinded the latter to what steps were necessary to keep the CEO in check.
Like Weldon they stood to gain hefty financial bonuses in the event a successful IPO or trade sale was achieved.
But the trouble was, they forgot about the tribe.
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