From the twenty-seventh floor window most of what you can see is still Len's domain. If you take the lift down to Albert St and jump into a car and speed off, in any direction, after an hour you'd still be driving through suburbs and past homes of people that, more likely than not, have voted for him.
While the view from the tower is grand, the building itself - much like Brown's tenure within it - has its flaws. When the Weekend Herald visited Auckland Council's headquarters $30 million of ongoing remedial work had fenced off half the street entrances and abseiling repair crews were operating right outside his spacious interview room.
The building, bought in 2012 for $104m, was later found to require extensive recladding as exterior slabs of granite were found to be at risk of falling on to the streets below. The public face of the council's headquarters required complete replacement as it was deemed too risky to stay on.
Brown isn't staying on either.
The singing mayor; the rapping mayor; the face-slapping mayor; the first mayor of the Super City - is dressed in a sharp black suit but insists it's not for a funeral. A week from today, when the votes are counted in the first local body election in 24 years not featuring Brown's name on the ballot, his council watch will be ended.
He's not retiring, despite he and wife Shan Inglis moving next month to a new home in horse-and-pasture country at Karaka.
Today Brown celebrates his 60th birthday, normally an age where politicians have the time of their professional lives. But Brown is no ordinary politician: he's a man who's made a habit of dying in public.
He leaves a complicated legacy. He's largely responsible for one of the largest infrastructure projects in the nations' history, as well as one of its most salacious sex scandals. His oft-mocked common touch - honed in the markets, churches and community halls of South Auckland - is based on keen interpersonal skills that seem to work equally well on prime ministers.
Brown has twice died in public. The first, in 2008, was on stage and from a heart attack. The second, slower but even more in the spotlight, was from the drawn-out disclosure in blog posts, newspaper front pages and inquiry reports of his affair with Bevan Chuang.
"In my political career over nine years I've suffered a near-death experience both personally and politically. Both of them were intensely traumatic to me and my closest," he says.
The heart attack came during the Pacific Music Awards while he was, by his own admission, "doing a bit of very poor rapping" from the stage. "And I just keeled over."
A weeks-long stay in hospital followed, including major surgery and complications that at one stage led to the last rites being arranged.
"I have no recollection at all of that event, or two days after that. I certainly didn't have a sense of 'oh this is what it's like to die' because I just lost all my memory. The second that I awoke after the operation four days later, I knew exactly what I had been through and was unbelievably happy to be alive," he says.
The other death he unfortunately remembers too well. News of the Chuang affair broke in the days after his 2013 re-election and persisted for months.
Brown says describing the fallout "unpleasant" would be "the understatement of the century, not least of all for my wife and family. It was traumatic. There's not a lot I want to say about that. I never said much about it. It's just part of my life that I'll have to live with."
He laughs off suggestions he was tempted to face Cameron Slater - whose Whale Oil blog broke the story - in the boxing ring when the blogger participated in the Fight for Life.
"I've been attacked by experts over the years. I just never wanted to lower myself to that. It is what it is, and you live a life: you make mistakes. And people will try to profit out of that," Brown says.
Brown insists his departure from the mayoral office is entirely unrelated to this fracas - "This is not the way things are at all," he says - claiming a long-held intention to only serve three mayoral terms.
This interpretation is disputed by several members of Brown's former mayoral and campaign team who say that within a few months of the affair becoming public, and with controversy still swirling, Brown was a dead man walking.
"It was discussed early on, that 'He won't get f***ed for f***ing, he'd get f***ed for something else'," one adviser says.
The straw that eventually broke backing for Brown was said to be the EY inquiry - which Brown was embarrassingly forced to part pay for - into whether he misused council resources in his pursuit of Chuang.
While the report cleared him of substantive wrongdoing, its comprehensive litany of sext messages and upgraded hotel-room rendezvous were considered terminally damaging.
His advisers summoned him to a meeting last February where it was made clear that Labour Party support in this years' election - including fundraising and a substantial vote-getting ground game - had defected to Phil Goff.
The following month, while Brown was understood to still be taking soundings of his prospects, news of the showdown broke in the Herald. A week after this front page revelation, Brown and his wife settled on the purchase of the block of land in Karaka where their new home out of the city has been built. (Brown says of this timing: "You are most definitely reading too much into that.")
While wistful at missed opportunities, the advisers fondly recount the two-stages victory of the first Super City mayoral campaign. The first involved building a profile for Brown in a Game of Thrones-esque series of manoeuvres also designed to dissuade Labour Party rivals from running.
This strategy involved declaring early - more than a year before the election proper - and timing this surprise announcement with a billboard campaign which also involved placing pro-Brown advertisements directly outside the Auckland Regional Council offices of rival Mike Lee.
With the field thus cleared, the campaign proper was based on the 2008 Brisbane city election - also involving a freshly-amalgamated council - where a candidate championing outer suburbs triumphed over a CBD-based rival.
The resulting campaign - where Brown happily recalls entering some sort of preternatural campaign zone during more than 300 public appearances - was a smashing success with Brown winning 48 per cent of the vote to John Banks' 35 per cent.
(Despite the turbulence that followed, it isn't clear whether anyone else on that inaugural Super City mayoral ballot would have had a less-controversial term in office. Banks was prosecuted and convicted - although later exonerated on appeal - of filing a false electoral return over donations to this mayoral campaign. And the third-place getter? Colin Craig.)
At the subsequent victory party on One Tree Hill, Brown accepted congratulations in person from then-Labour leader Phil Goff, but amid celebrations missed a similar phone call from the Prime Minister.
He was able to make good on this missed contact shortly afterwards when John Key paid a visit to Brown's soon-to-be-departed offices in Manukau. At this meeting, according to a Brown adviser who was present, the Prime Minister and the incoming mayor reached an understanding of sorts on public transport issues.
"Len said 'I'm not going to get in the way of the Holiday Highway', and told Key 'Just give me more time to make the case for the CRL'," the adviser said.
Brown downplays the making of any explicit quid pro quo deal at this meeting, but says his lack of vocal opposition to the Puhoi-Wellsford highway upgrade - and a similar silence over the controversial pokies-for-convention centre deal struck with SkyCity - served a pragmatic purpose.
"What I was doing was building trust. And while it took some of them [in government] a while, certainly the Prime Minister learned to trust me at a quicker pace than others. He's an approachable guy, and he's pragmatic. We always got on well both personally and politically," he says.
Brown acknowledges his relationship with other Cabinet members was occasionally more headbutt than a meeting of minds. "I've got a real thick skull, thick hide too. But there was never any headbutting with John Key: you just don't need to do that."
The pragmatism seems to have paid off: Brown is widely credited, at least in part, for seeing government attitudes to the CRL soften until, earlier this year, it loosened the purse strings and committed funding half of the $3.4b project.
Brown says he focused on the rail link as its presence on the drawing board for so many decades had started to become the city's albatross. "The CRL has become something of a metaphor for Auckland's inability to achieve anything. I felt if we could achieve that we could achieve anything," he says.
He says he's similarly proud of rolling out a region-wide 30-year transport plan, and his former advisers say Brown succeeded in settling much debate around city planning.
"No one now questions the direction of the city. You will not be elected today if you're not pro public transport. You can't rip up planning rule books promoting intensification along transport routes. History will remember him a lot more fondly than the contemporary assessment," one adviser says.
After making public his intention late last year to not run again, Brown has had time to ponder his future. While keen to take time to "smell the roses", he says he's had some discussions - "I'm talking to a number of international organisations" - about a working life outside of council.
He says his experience amalgamating local councils and running a city coping with disproportionate growth was in demand. There are lots of learnings here that could be useful in a discussion for good, efficient, effective and well-managed change in cities globally," he says.
This future, however, is yet unwritten. "There no contract signed, but I'm working on that."
If he had to write his epitaph he'd be happy with "He Gave His Best" and given a chance to freestyle at the end of an hour discussing his past and future, Brown is at a loss of what fresh observation he could give.
"As the singing mayor of Auckland I don't think there's much I haven't let rip on, really," he says.
He nonetheless starts an ode to determination: "I've tried to be fearless in the job. You can have all the dreams and schemes and visions: none of them will mean anything if you do not have the will."
It's late on a Friday afternoon and the finish line to a long public career is in sight. Brown seems to be losing steam but soldiers on to answer this one last question.
"That's been my ballast: just don't be afraid; just go for it. By and large, it's worked out. I've got nothing more to say."
John Banks lets loose
Two-time Mayor of Auckland John Banks begins his assessment of his rivalry with Len Brown magnanimously - "The people of Auckland voted for Len Brown, and voted against me. He won the election fairly and squarely" - before blaming electoral fraud and third-party candidates for his 2010 defeat.
"It's arguable I would have won the mayoralty if the God-fearing Colin Craig hadn't run. He was the ultimate spoiler for the centre-right, and nothing has changed on that front," Banks says. It's probably worth noting that Brown's 13-point margin of victory appears to somewhat exceed Craig's 9 per cent share of the vote.
Banks also says a conviction for electoral fraud (Daljit Singh registered hundreds of people to vote in the 2010 race, providing a single Otara address) proves "we have such a discredited form of voting".
Banks also discounts Brown's flesh-pressing abilities as "being exceptional at high-fives, hongis and glad-handing" and declares: "His mayoralty has been at least disappointing, and at worst disastrous."
But despite the sharp criticism, Banks reserves his most cutting lines for his own sides' inability to mount a single credible challenge to the man widely tipped to take over.
"The centre-right has been a shambles and Phil Goff will be elected by default," he says.
"The National Party told me in no uncertain terms that if I was to stand aside they would pick a high-profile, highly-talented and brilliant woman candidate and wipe the floor with the centre-left. I told them I live on the 23rd floor of an apartment building and haven't yet seen pigs fly past the window."
Banks said the National Party had missed a trick and failed to exploit its recent dominance in general elections.
"They haven't truly engaged with the reality and importance of a successful Super City driving the New Zealand economy and our standard of living. They haven't grasped that, hence they haven't put up high-quality candidates: same old hacks; same old desperate; and very little new blood."