There’s something in the water when it comes to Wellington’s recent political history — and the name Justin Lester keeps floating to the top.

Lester, who served as Mayor of Wellington from 2016 to 2019, has kept a relatively low political profile since losing office. But recent moves online, coupled with past controversies, are dragging old questions back into the light. And, Wellingtonians are asking: Was everything above board during Lester’s time in charge?

Shelly Bay: A Development or a Deal?

The Shelly Bay development saga remains one of Wellington’s most divisive urban projects. At the centre of it? Property developer Ian Cassels and his firm, The Wellington Company — the same developer who made a financial donation to Lester’s 2016 mayoral campaign.

Now, a $2,000 campaign donation doesn’t scream corruption — but when that same mayor goes on to champion Cassels’ highly controversial redevelopment at Shelly Bay, some Wellingtonians couldn’t help but raise their eyebrows. The optics, if nothing else, were murky.

Yes, Lester technically recused himself from voting on the project — but is that enough when his public support for it continued loud and clear? Opponents of the plan, including high-profile locals like Sir Peter Jackson and members of Mau Whenua (a Taranaki Whānui breakaway group), argued the development disrespected the land and may not have followed proper process. In a city increasingly cynical about backroom dealings, this one didn’t pass the sniff test for many.

Was Lester simply doing what he thought was best for urban development — or was there more grease on the wheel than the public was told?

Let’s Get Wellington What, Exactly?

Then there’s the matter of Let’s Get Wellington Moving — the mega-budget $6.4 billion transport initiative. Under Lester’s mayoralty, the program ballooned into a bureaucratic black hole, eating up millions without delivering much in the way of actual movement.

Estimates suggest that around $90 million may have been spent before a single shovel hit the dirt. And while Lester wasn’t solely responsible — the program was a joint effort — many felt his leadership lacked the grip needed to keep such a massive initiative accountable. Some in the capital still question whether the money was mismanaged, or worse, funnelled into the wrong hands through bloated consultancy fees and politically convenient contracts.

Was it just inefficient government, or were some players a little too cosy with suppliers and stakeholders?

Facebook Face-Off: From Mayor to “Wellington Alive”

Since leaving office, Lester’s behaviour online has raised eyebrows for a whole new reason. In what many see as a calculated swipe at popular local community page Wellington LIVE, Lester has recently rebranded his personal Facebook account as Wellington ALIVE — a near-identical name clearly designed to confuse or leech followers.

It’s not just a rebrand. He’s reportedly been trolling the original Wellington LIVE team, posting jabs, harassing admins, and even going so far as to DM family members of the page’s team with inappropriate and abusive messages. Screenshots making the rounds in private circles suggest a level of online hostility unbecoming of a former public figure.

Petty? Sure. But it paints a picture of a man more interested in clout and control than community.

Patterns or Coincidences?

In isolation, each of these incidents — the campaign donations, the urban development approvals, the failed infrastructure spend-up, and now the digital antics — might not scream scandal. But when taken together, a pattern begins to emerge: one where political power, private developers, public money, and personal grudges swirl uncomfortably close together.

No smoking gun? Maybe. But where there’s this much smoke, it’s fair for the public to ask who’s holding the matches.