Four hundred issues. Four hundred!
I know I say this at every milestone, but it really is just so enormously cool that this little indie newsletter has been able to survive and grow and thrive like it has. Thank you for reading and supporting this work.
You wouldn’t necessarily think there’d be such a strong market for a hyper-obsessed municipal government newsletter that routinely runs thousands of words each week, but then I suppose we’re all mad here.
Speaking of mad:
Thanks to Joy San for contributing the cover art for this milestone issue. It’s definitely the most surreal cover yet, and I love it for that. Where else are you going to see mayoral candidates playing croquet, using a squirrel for a ball and geese for mallets, overseen by a deranged Cheshire raccoon that bears a striking resemblance to someone?
You can check out more of Joy’s work and commission your own art on her website.
This issue isn’t just big because it happens to be a round-number issue. It’s also big because there’s a lot packed into it. I’ve got a new edition of LOBBYIST WATCH and the launch of a new regular feature covering the latest from the 25 ward races.
But before that, there’s the big headline: the launch of a brand new interactive feature that, I hope, will help you figure out how much you align with your local councillor. I’m calling it SimCouncillor.
Let’s check it out.
✨ This issue runs a bit long. If it gets cut off in your email client, read it on the web.
— Matt Elliott
matt@cityhallwatcher.com / Archives / Subscribe
Introducing SimCouncillor: Tell us how you’d have voted — and find your match
Over the last three years, I’ve collected the results from over 100 important Council votes taken by Mayor Olivia Chow and Council and fed them to the COUNCIL SCORECARD. The Scorecard allows for all kinds of useful analysis about how councillors operate: their ideological disposition, their loyalty to the mayor and any and all shifts in perspective over time.
All this data is also useful, it turns out, in the context of a municipal election.
Launching today, SimCouncillor puts you right in the fancy shoes of your local councillor. You’ll be presented with 15 real votes and asked how you’d vote. Just like in the real Council Chamber, there’s no way to abstain. On some issues, you’ll have to consider whether it makes sense to compromise, or whether you’d like to stay rigid and hold out for a better outcome. Some issues will seem hyperlocal, and maybe require you to do a bit of research. (Like, does anyone really remember what that dispute over the Humber Yacht Club was actually about?)
You don’t have to stand up and give a five-minute speech explaining how you’d vote, but you can, if you’d like. Your cat, or your kid, or your coworkers, might like it.
After running through a set of 15 questions — and maybe a few tiebreakers — SimCouncillor will tell you a few things:
How your views compare with the two members of Council running for mayor: Mayor Olivia Chow and Councillor Brad Bradford.
How your views compare to your local councillor.
Who your closest match on Council is.
It only takes a minute or two, so try it out. Choose some priority categories if you care more about some issues — you’ll be guaranteed to get more of those kinds of questions in your random set, and scoring for those issues will count more.
You can take a quick screenshot to share your results with friends. They’ll probably be like, “Wow, a municipal politics game? I’m cancelling my GTA 6 preorder! This is all the fun I need!”
I mean, maybe. It’s plausible.
Results are 100% anonymous. I can’t trace them back to you, even if I wanted to — and I don’t! But I will be regularly reporting on how many people match with each member of Council, though. I’m curious to see if anyone else in the world could possibly have the exact same views of some councillors. It’ll be a fun experiment.
Try it out and let me know if you have any feedback or notice any bugs.
Special thanks to Andrey Levkovski for his help vetting the questions and testing the app.
Pretty cool, right? If you like this kind of thing and want to support more independent journalism, consider becoming a City Hall Watcher subscriber. It costs just six bucks a month or sixty bucks a year, plus HST.
Lobbyist Watch for August 2026: Waymo rolls on, Oracle sees an opening, and more
Lobbyist Watch is City Hall Watcher’s monthly summary of activity on Toronto City Hall’s Lobbyist Registry. In August 2026, City Hall Watcher reviewed 258 registered lobbyist communications and 74 new subject matter registrations.
Disclaimer: Toronto’s Lobbyist Registry requires lobbyists to register and record all communications they have with politicians and staff, but it does not require them to provide much detail about the extent of those communications. As a result, a meeting noted below could be a long conversation with some deal-making or a passing chat of no real consequence. The data presented below is current as of September 4, 2026.
A bit more Waymo
Robotaxi service Waymo continues to try to steer its way to establishing service in Toronto. On August 12, the company — a subsidiary of Google — sent Head of International Policy & Government Affairs George Ivanov and Head of Public Policy for Canada Caitlin McClung to meet with Adam Chaleff, the mayor’s Director of Legislative Affairs & Issues Management. The trio met on August 12.
McClung appears to be a new addition to the self-driving effort. She previously worked as a public affairs director for Restaurant Brands International. She was also a director at StrategyCorp and worked for the provincial government in the Dalton McGuinty era.
McClung’s registration tells us her job is to talk up “the potential development of by-laws and regulations related to autonomous driving technologies, including as it relates to operational authorizations, commercial operations, goods delivery operations and ridehail operations.”
Sabrina Geremia, a longtime Googler who currently serves as VP & Country Managing Director for Canada, is listed as the Senior Officer on the file.
In addition to the McClung and Ivanov meeting with Chaleff, Waymo also continues to employ the services of StrategyCorp’s Aidan Grove-White. Grove-White met with staff from Transportation Services on August 10.
Ask the Oracle
Senior staff from City Hall’s Technology Services division heard much from the Oracle in August. Reps from Oracle America, the tech company founded by billionaire Larry Ellison, logged 20 communications to City staff.
The company is pitching their products and services, including “cloud applications, platform services and engineered systems.” A contingent of staffers met with a large Oracle contingent on August 13. The meeting was followed by an email to Deputy City Manager for Corporate Services Sonia Brar on August 23.
The meetings, of course, come in the midst of an escalating trade war with the United States. Ellison has been a staunch supporter of the current U.S. administration.
Lobbying grab bag
Reps for engineering firm AECOM logged a big meeting with senior staff from Toronto Water on August 27. The company has a long history helping the City upgrade wastewater facilities and other water-related infrastructure.
SmartCentres seemingly has some issues with the signage at the Vaughan Metropolitan Centre subway station. Maybe it’s because the name is ridiculously long and probably pretty hard to fit on a lot of signs? Anyway, Grant Gonzales, Director of Corporate Affairs for SmartCentres REIT, logged a meeting with senior staff at the TTC on August 25 to discuss the matter. The meeting included reps from the transit agency’s Wayfinding & Signage department and the Marketing department.
Raly Chakarova, Executive Director of the Toronto and Area Road Builders Association, logged a meeting with Chief Procurement Officer Geneviève Sharkey on August 12.
Dr. Kenneth Chan, a partner with professional services firm Optimus SBR, logged meetings with Councillor Chris Moise, Councillor Rachel Chernos Lin, Councillor Josh Matlow and Medical Officer of Health Michelle Murti on August 18. Chan is part of an effort to pitch City Hall on Optimus’ services. They’d probably describe them as prime.
Representing restaurant group Pegasus, lobbyist Kim Wright logged a meeting with senior staff from City Planning and Corporate Real Estate Management on August 28. The company’s portfolio includes The Wheat Sheaf, O’Grady’s, Palais Royale, Figo and more.
Lyft Canada’s Public Policy Manager Amanda Arella logged meetings with Craig Ruttan, chief of staff to Councillor Brad Bradford, and Adam Chaleff, senior staffer to the mayor, on August 4. Stefano Hollands from Crestview Strategy logged the same meetings as part of the lobbying firm’s work with Lyft.
Tech 4 sale
Ouster Canada, makers of tech that uses LIDAR sensors to optimize traffic signal timing, has registered to pitch their tech to City Hall. No communications yet.
Global Public Affairs’ Ellen Chin was keeping busy representing eStruxture Data Centers as the company continues to look for opportunities to convince City Hall of the virtues of data centres. She logged several phone calls and emails to staff with Toronto Building, City Planning, Development Review and the Environment division. On August 12, she logged a meeting with Environment, Climate & Forestry Executive Director James Nowlan.
The City continues to see vendor presentations from cybersecurity companies. In August, they heard from Cybersnap, Beauceron Security, Hoxhunt, Kyndryl and others.
Code 4 Canada CEO Dorothy Eng and Director of Partnerships Andrew Lui logged meetings with staff from Transportation Services and Technology Services, hoping to discuss the City’s “digital capacity to design, develop and deliver user-centric public services that meet people's needs.”
Familiar faces
Kema Joseph, a former advisor to John Tory, is representing the Coalition of Innovation Leaders Advancing Respect. These CILARs are looking to gain City support for things like “inclusive AI and digital-skills training, mentorship, career pathways and entrepreneurship opportunities.” Joseph met with current mayoral advisor Adam Chaleff on September 2.
Amir Remtulla, long ago the chief of staff to former mayor Rob Ford, is representing beer giant Molson Coors. The company has some concerns about the City’s sewer surcharge.
Toronto’s top lobbying charts for August 2026
Most Lobbied Officials: Adam Chaleff, Mayor’s Office (9 communications); Sebastien Gibson, Councillor Matlow’s Office (4); Nika Lennox, Councillor Matlow’s Office (4); Councillor Lily Cheng (4); Craig Ruttan, Councillor Bradford’s Office (4)
Lobbyist Watch will return in October.
Candidate Chaos: Labour Day labour endorsements, Nunziata and Padovani get into a heated rivalry, John Tory lurks
The mayoral race gets all the attention, but there are also 25 separate contests for Council seats happening. Here are some tidbits from the CANDIDATE CHAOS of the last week.
A TORY STORY: It’s not clear yet how much of an active role former mayor John Tory will play in this fall’s elections, but a pair of sitting councillors are claiming his endorsement. Both Councillor Mike Colle and Councillor Frances Nunziata have posts saying they’ve got the backing of the longtime mayor.
LABOUR OF LOVE: Candidates were out in force at the Labour Day parade yesterday, expressing their appreciation for unions. But the love isn’t necessarily 100% mutual in all cases. Both CUPE Local 79 and the Toronto & York Region Labour Council have come out with slates of endorsements. CUPE 416 has so far endorsed just one candidate: Beaches-East York’s Natalie Johnson.
Here’s where things stand:
ALSO ENDORSED: Colle also has the support of MP Marco Mendicino, while Nunziata is counting the support of MP (and former councillor) Jennifer McKelvie. Diana Yoon scored a notable endorsement in University-Rosedale, getting the backing of former MPP Suze Morrison. Councillor Chris Moise, meanwhile, earned kudos — and an endorsement — from former Medical Officer of Health and noted scarf aficionado Eileen de Villa.
In Scarborough North, challenger Han Dong is touting the support of CK Fung, husband of the late former councillor Cynthia Lai. And it seems notable that Conservative MP Melissa Lantsman is guesting at a fundraising event for Willowdale challenger Ardeshir Zarazade.
TURNING UP THE HEAT: In York South — Weston, challenger Chiara Padovani and Councillor Frances Nunziata have developed something of a heated rivalry over the idea of a max temperature bylaw.
Padovani posted a video with a lot of hot-weather effects and footage of people fanning themselves, claiming Nunziata “recently voted to kick the can down the road, pushing a decision on a Maximum Heat Bylaw to next summer.”
Nunziata fired back, saying “some people either can’t read or are disingenuous with the facts.”
“To be clear,” she wrote, “I voted with Mayor Olivia Chow and 21 other members of Council to move forward with a maximum indoor temperature by-law and to bring it back for approval by June 2027.”
But what do the facts say? Well, as is often the case with this stuff, it’s a bit complicated. There have been a lot of votes on the question of a maximum temperature bylaw over the years. Nunziata has generally been supportive of the idea. This dispute centres on a vote from May 2026, in which Councillor Josh Matlow moved to accelerate the development of a bylaw so that it’d be ready for June 2026.
Several councillors, including members of the mayor’s Executive Committee like Councillor Alejandra Bravo and Councillor Gord Perks, argued at the time that this was not a realistic timeline. The Matlow motion was defeated 8-16, with Nunziata on the opposing side. (Notably, both Mayor Olivia Chow and Councillor Brad Bradford supported the accelerated timeline motion.)
So Padovani is right to point out that Nunziata was opposed to a motion to speed up implementation of a maximum temperature bylaw, but with the caveat that Nunziata was far from alone in believing that the motion was not realistic.
Nunziata can instead point to her support of another motion moved and passed by Bravo at the same meeting, calling for the development of a “framework” for a maximum temperature bylaw. That motion led to a subsequent debate at the June Council meeting in which Council voted 23-1, with Nunziata joining the majority, in favour of developing a bylaw for June 2027.
BRIEFLY:
Toronto Centre candidate Curren Stikuts is pledging to expand the operating hours at Riverdale Farm.
Former councillor Mike Layton is making me jealous with his cool cargo bike.
Both Councillor Jamaal Myers and challenger Han Dong ended up at the opening of the Toronto Zoo’s new glow-in-the-dark exhibit. Looks pretty trippy.
Councillor Josh Matlow shared a post pointing out that the torrential rain last week didn’t seem to cause the roof to cave in at the Ontario Science Centre. Go figure.
Scarborough Centre candidate Krissan Veerasingam raised some money by hosting a food tour.
In Etobicoke North, challenger Chloe Brown has signed something called the Community-Led Planning Champion Pledge. “I believe in a holistic approach to development that empowers our youth, supports local businesses, and meets the needs of working-class families,” she says. The pledge is a project of the Coalition for Responsible Community Development. Thirty-three other candidates have signed so far.
News briefs are compiled primarily from Instagram posts. If you’re a candidate and haven’t been followed by the official City Hall Watcher account, get in touch, and we’ll add you.
The week at Toronto City Hall
THURSDAY: 🎭 The TO Live Board meets on Thursday to discuss the City’s theatres. An update from the Corporate Real Estate Management division reveals that two options for fixing up the St. Lawrence Centre for the Performing Arts will be presented in January. Option One will be a more bare-bones $84 million reno. Option Two will include “enhanced upgrades” but will require additional philanthropic and federal government funding.
NEXT WEEK: A special Council meeting scheduled for September 16 was cancelled. Dry your tears. It’s going to be okay.
Weekly wrap
📽️ ELECTION PROJECTION: City Hall Watcher’s Election Projection remains unchanged as we wait for new polling.
But here’s something new: School boards are now tracked in our election dashboard! You can see each trustee election, including where incumbents are running, as well as the wards that have already been decided by acclamation. View the full projection by Alex Olson.
📊 CouncilScorecard.ca ACCESS CODE: Subscribe to get access
🗳️ CANDID CANDIDATES: The 2026 Election Candidate Tracker remains available. I’ve added a section at the bottom listing registered third-party advertisers. As of today, there are four registered: ABC Advertising Company, More Neighbours Toronto, R. Michael Teper, and United Steelworkers USW.
🪧 SIGNS OF THE TIMES: 875 QUEEN ST E: Firehouse Subs; 3278 MIDLAND AVE: Molly Tea; 5 GRENOBLE DR: Flemmingdon Park Community Church; 0 BOROUGH DR: Alta at STC; 55 BLOOR ST W: Spier & Mackay; 801 BAY ST: Infinity Vape; 101 STOKES ST: Camh; 250A QUEENS QUAY W: Rabba Fine Foods; 3478 LAWRENCE AVE E: Angara Indian & Hakka Cuisine; 44 FASKEN DR: Budget Shelves; 0 SHAW ST: Camh; 5845-5955 LESLIE ST: Tim Horton; 150 SILVER REIGN DR: Poulet Rouge; 1050 MILITARY TRL: University Of Toronto; 2280 DUNDAS ST W: Shoppers Drug Mart; 1245 DUPONT ST: Pet Valu; 1142 CASTLEFIELD AVE: Bloomsbury Fine Cabinetry; 20 WELLINGTON ST E: Axis Therapy & Performance; 1780 MARKHAM RD: Punjabi Haveli; 1350-1400 CASTLEFIELD AVE: Fit 4 Less; 100 CONSILIUM PL: Hitachi; 5 EIREANN QUAY: Corleck; 365 PARLIAMENT ST: Bmo; 8450 SHEPPARD AVE E: Rouge Valley Community Recreation Centre; 45 EAST LIBERTY ST: Tim Hortons; 23 SPADINA AVE: Concord City Place Way; 70 CALEDONIA PARK RD: Nest; 200 WILMINGTON AVE: Honey & Barry Sherman Campus; 3250 MARKHAM RD: Marquee; 900 DUFFERIN ST: Canadian Blood Service. (Sign Permit Applications since August 31, 2026)
City Hall Watcher #400
Thanks for reading! That’s four hundred issues done and dusted. Next week: our highway series continues with Issue 401. But don’t worry: after much consideration, I have decided NOT to sell Issue 407 to an international conglomerate of investors.
If you liked this issue — and the 399 that came before it — tell a pal.
Congrats on 400!
Congrats on hitting #400, Matt! Here's to local journalism