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TBM mechanic Riaz Ishmail is pictured in front of the Tunnel Boring Machine as politicians speak to the media about the new Eglinton Crosstown construction site in Toronto on Tuesday April 9, 2013.Chris Young/The Globe and Mail

It was the 1910 equivalent of "subways, subways, subways."

Horatio Hocken ran for Toronto mayor in that year's election on a platform of "Tubes for the People." The ambitious scheme called for underground streetcars running into the downtown from three directions, at a cost of $500-million in today's dollars.

Voters supported the plan, but Mr. Hocken lost the race, and the man who took office killed it. Rejigged to lose its routes from the east and west, a plan for a north-south underground was presented again a few years later, at one-fifth the cost, and this time voters balked.

Nothing was built underground until four decades later.

A recent e-book by Ed Levy, a transportation consultant and transit historian, traces this sad story from the earliest ideas to a series of abortive plans through the postwar era. The constant theme of Rapid Transit in Toronto: A Century of Plans, Progress, Politics & Paralysis is the sense of squandered potential.

The discouraging reality is that, while transit expansion is the focus of a rising tide of public debate, the city has been grappling with many of the same questions for a century. And we're still arguing.

A relief line that would take pressure off the north-south routes has been proposed so many times it occasionally feels like a bit of a punchline. But it's as necessary as ever and is once again the TTC's top priority, according CEO Andy Byford.

A council debate this week hinted at why it's been so hard to achieve, though. Ostensibly about transit funding, the debate degenerated into a parade of councillors presenting wish-lists for their wards. After rejecting most funding tools, they passed motions in support of various new transit projects, even as provincial Transportation Minister Glen Murray insisted the work underway would not be changed.

In an interview, Mr. Levy said his project started as a way to collect the most relevant maps and documents from a century of transit planning. But he soon realized he would have to add context – in essence, explain how things kept going wrong.

The regional transit agency Metrolinx hopes to break free of this history and is trying to avoid some of the mistakes of the past. Its non-political board should, in theory, make it less susceptible to the whims of those chasing votes. And it is in the final stages of devising an investment strategy that would produce a steady stream of predictable revenue to fund its $34-billion "next wave" of transit expansion.

The plan is also rooted in some of the better ideas of the past. It includes a line coming into the downtown from the east – dubbed the Downtown Relief Line – an early version of which was proposed in the 1910 plan and which has come up again and again through the decades. An early hint of the Eglinton Crosstown currently under construction can be seen in a 1941 plan to run rapid transit as far as Dufferin in its own right-of-way, on the old Belt Line.

Metrolinx's plan is based on a grid network, though, recognizing the modern reality that not everyone wants to be funnelled downtown. Better transit in the suburbs may also have the bonus of lessening the resentment that helps explain why a downtown relief line has been proposed repeatedly and never built.

Mr. Levy says that the fact that another downtown subway has yet to be built is appalling, and he blames this on parochial suburbanites. "Most of the population is outside the old (City of Toronto)," he said this week. "The most difficult thing is to get people out there to realize that a major improvement downtown will help everybody."

A corollary to the suburban-urban divide is the persistent – and pricey – notion that everything but subways is second-class transit. Mayor Rob Ford and his allies hold this argument dear, and this week's council debate heard proposals for subways on a whole series of new routes.

"There has always been this problem that we want the most expensive option," said Steve Munro, a blogger and activist who has watched transit in this city for decades. "We'll save our pennies and eventually we'll have enough money to build a subway. One. So the political battles are all about who will get the next subway."

At the Feeling Congested? public meetings recently held by the city to tackle gridlock, one of the display panels combined decades of transit plans. In the unlikely event that all had been built, Toronto would enjoy the extensive sort of transit system familiar to Parisians or New Yorkers. Instead, plan followed plan into the dustbin. Almost nothing was built.

"It makes you want to cry," said a participant at the meeting in the west end.

Of course, not all urban transportation schemes are equally valid. Mr. Levy describes many that look foolish in retrospect.

The cancelled 1960s proposal to run an expressway down Spadina, which was stopped after residents fought tooth and nail, is often pointed to as proof that every plan has to be open to change. And Mr. Levy found evidence of a 1943 idea for an east-west route known as Superhighway E – running just north of Bloor in a broad trench that would include streetcar lines and at least four lanes of traffic – that didn't survive into the next decade.

"Surely, this 70-year-old proposal must be seen as either naïve in the extreme or too far beyond being economically or politically feasible to merit serious consideration," he writes.

The underground streetcars proposed in the early 20th century could have hampered the city for decades, with a low-volume existing system postponing the development of proper heavy-rail subways. And sporadic plans to run transit lines along ravines were shown to be foolhardy after Hurricane Hazel sent floodwaters through them in 1954.

Still, the good ideas have been around for decades. And Mr. Levy warns that there is little time to waste after "screwing around" for another generation.

"We're great at doing studies in the city. Oh, boy, are we expert at that," he said. "We're a city of missed opportunities."

Oliver Moore is The Globe and Mail's urban transportation reporter. In a previous life he worked on the short-lived Eglinton subway project, which did not survive Mike Harris's Conservative government.

Mr. Levy will speak about transit Monday at Urbanspace Gallery, 401 Richmond St. West, at 6 p.m.