After nearly three decades as a councillor, Joe Mihevc has filled around 250 storage boxes full of stuff.

Reports, agendas, mementos — they're all packed away. Standing in his now-empty purple office, the outgoing representative for Ward 21 points to the last few trinkets on his table and bookcase: Two model GO trains and commemorative plaques for events like Caribana and the opening of the Wychwood Barns, the arts and cultural space he helped establish a decade ago in of a century-old streetcar facility.

Each one, he says, reminds him of time spent working in this "magical city."

"A lot has changed," adds Mihevc, who first served as a councillor in the former city of York before amalgamation.

"And the struggles we have now with technology and fast media and issues like supervised injection sites and overdose prevention sites and homelessness ... those are things that the next generation is going to have to sort out."

That next generation — a mix of mostly familiar faces and three newcomers — will be sworn in on Tuesday, with this week marking the departure of half of the current 44 councillors.

Some, like Janet Davis and Glenn De Baeremaeker, chose not to run again, either out of a desire to retire from political life or because Premier Doug Ford's controversial mid-election council cuts made their chance of winning in the new 25-ward system slim.

Others were defeated in competitive council races between incumbents, including Mihevc, who lost to Josh Matlow by roughly 4,200 votes.

"I leave here with a deep sense of gratitude that I was part of history," Mihevc says with a smile.

The typically-buzzing hallways encircling city hall's second floor are quiet now, with many offices nearly packed up, while others — including that of bombastic outgoing councillor Giorgio Mammoliti, who lost his race to incumbent Anthony Perruzza ​— have long been empty and dark.

During the October election, Norm Kelly lost in Scarborough to fellow incumbent Jim Karygiannis by 2,600 votes. One afternoon at his nearly-bare desk, he's busy signing election signs as his staff pack up the last few boxes.

It's a fitting visual from the veteran councillor-turned-local-celebrity, whose claim to fame in recent years was a Twitter account where Kelly posts quips and memes about city life — the 77-year-old admits to stealing many of those ideas — or weighs in on hip hop feuds to his roughly 740,000 followers.

"TMZ has called me a number of times over the years," Kelly says. "On one of those occasions they asked me, what has Drake brought to the city? And my response was: an attitude."

The things you find when cleaning out your office... <a href="https://t.co/FuoETCVMA4">pic.twitter.com/FuoETCVMA4</a> —@norm

Kelly first entered politics as an alderman on the borough council of Scarborough back in 1974, marking the start of his long career at the federal and municipal level. He watched entire families grow up, attending picnics, marriages — even funerals — over the decades.

"Over my political lifetime, the city has become multicultural and international in its texture, in its feel, in its appearance," Kelly recalls. "The dynamism, the creativity that has been generated as a result has been incredible."

People used to wonder where Toronto was on a map, he adds. "Today, people know. Canadians don't like to brag, but I think Torontonians should."

But the city and its leaders will face challenges in the years ahead, says outgoing councillor Josh Colle, who plans to return to private industry after stepping down — a move that made room for his father, longtime politician Mike Colle, to enter the race.

After eight years on council for Ward 15 Eglinton-Lawrence, including his most recent stint as chair of the TTC board, the younger Colle became deeply familiar with the transit file.

"The jurisdictional wrangling has to stop," he says. "There has to be a sense of greater clarity on who does what in the region on all facets of transit building and operations."

And there's much to discuss: The long-awaited relief line. The Scarborough subway. The province's promised TTC upload.

"The world is changing so quickly and it's not going to just be about traditional mass public transit," Colle adds.

"The reality is, people access mobility services of so many different kinds and in so many different ways that the city has to get a handle on that and get up to speed with technology and innovation and the way people expect to be served."

After nearly three decades as a councillor, Joe Mihevc is packing up his office and figuring out what comes next. (Paul Smith/CBC News)

His fellow outgoing councillor Mary-Margaret McMahon, who also served two terms in the Beaches-East York area, says the biggest challenge for those taking the reins is simply how to handle their workload, with thousands more residents in each of the 25 geographically-larger wards imposed on Toronto by the province.

"I don't know how they're going to manage," she says.

In her office, now cluttered with storage boxes, the term-limit advocate holds up a massive gold cardboard key given to her by residents following the reopening of a stretch of roadway after a lengthy infrastructure project — an honour dubbed the "Key to Kingston Road," McMahon says.

It's one of her fondest memories, but other moments at city hall were more bizarre or tumultuous. "I would like to write a book, actually," she jokes. "Maybe a screenplay."

There was the Rob Ford era, where councillors had to avoid paparazzi-like reporters as the media followed every move of the beleaguered former mayor amid reports of his heavy drinking and drug use.

And there were the late nights of squabbling in the clamshell, McMahon recalls, including one hours-long council debate over whether or not to have sandwiches. "I wanted to quit my job before I even started," she says with a laugh.

In Mihevc's case, he never felt it was time to quit, and he still doesn't feel ready to leave.

"I do believe there is such a thing as public good," he says. "My hope, frankly, for incoming councillors and communities, as well, is that you seize it. If you have that project that you know is going to be something good for a neighbourhood, grab it. Do it. Have a passion around it. And you'll see real changes."

Looking back at the last few mementos in the office where he spent decades of his life working, Mihevc pulls out one object in particular: A small gold clock presented to him by former mayor Mel Lastman at the inaugural meeting of Toronto's city council back in 1998.

Twenty years later, it's finally stopped ticking.