In the lead-up to a crucial vote during which city council flip-flopped on transit plans to approve a multibillion-dollar subway in Scarborough, Jennifer Keesmaat went on the warpath.

In July 2013, the progressive chief planner — whose departure after five years at the helm was announced on Monday — was trying to make it known to anyone who would listen that a seven-stop light-rail line the province had already agreed to pay for, and the city had already approved, was still the better option.

Hundreds of pages of emails obtained by the Star through freedom of information requests over the past two years show how Keesmaat became the subway’s strongest critic on staff and tried — but ultimately failed — to prevent what some have called the biggest boondoggle of Toronto transit politics.

The number of reasons why the three-stop subway was a bad idea added up, Keesmaat agreed in one such email, to an “embarrassment of riches.”

The push to build a subway in Scarborough was one of the most controversial projects advanced under Keesmaat’s tenure at city hall, one that has complicated her legacy as a progressive city-builder. A compromise plan she later moved under Mayor John Tory today continues to unravel.

This is the untold story of how she tried behind the scenes to prevent the subway from being approved in the first place.

By the first week of July 2013, the future of transit in Scarborough was in limbo.

A surprise and illegal motion from Scarborough councillor and subway backer Glenn De Baeremaeker at an earlier May meeting during a completely unrelated debate — a move supported by then mayor Rob Ford — saw council sending mixed messages. They had endorsed a subway while having a signed agreement with the province’s transit agency, Metrolinx, to build an LRT.

Metrolinx, unsurprisingly, demanded clarity, triggering another vote, which was scheduled for a July 16 council meeting.

City staff began preparing a report to help council decide how to proceed, meeting nightly at one point to meet the tight deadlines.

On July 2, Keesmaat emailed her superiors, then city manager Joe Pennachetti and deputy city manager John Livey.

She noted media reports that said TTC CEO Andy Byford was meeting Metrolinx officials to review the costs for proceeding with the subway following De Baeremaeker’s motion.

But Keesmaat was not convinced the subway should be built at all.

“As we have discussed, there are different opinions as to the validity/relevance of these motions,” Keesmaat wrote, referring to the re-opening of the debate.

“I am well aware of the issues,” Pennachetti responded, promising to convene a meeting of staff that day.

The next day, Keesmaat forwarded a proposed outline for the council report to Livey.

“This is the outline we are working with,” she wrote.

Importantly, the outline included an example of what the planning department believed should be recommended: “For the reasons presented, subway is not the preferred technology to meet the future planning and transportation vision for this part of the city.”

Several days later, Pennachetti asked a senior group of staff for further refinements to the draft report.

Keesmaat responded to that request to make a point: “The subway option DOES NOT make the list of (ten) priority projects when compared with other projects across the city.”

It was followed by a warning.

“The quickness of the turn around has meant that we are struggling with a rationale, fair means of assessment,” Keesmaat wrote.

Two days later, Keesmaat sent Byford an email with the subject line “LRT/Subway – URGENT.”

“It is my understanding that your support of a subway for Scarborough is based on the projected increase in ridership,” she began. “I would like a more fulsome understanding of (how) you attained this number.”

“I have not forecast more riders,” Byford responded. “We didn’t reopen this debate so (it’s) up to councillors to say if funds are available.”

The emails reference a ridership number that would soon appear in the final version of the July report.

Though earlier analysis estimated the number of subway rush-hour riders by 2031 would be 9,500. That number had suddenly grown to 14,000.

That number was rarely discussed in any emailed conversations obtained by the Star before that report was tabled.

But the increase came as a surprise to Keesmaat. She was unaware it had apparently come from her own planning department, not the TTC, as the final report would later state.

Keesmaat declined to comment for this story. When asked previously about this exchange, the chief planner admitted the analysis leading up to the July vote was both “rushed” and “problematic”.

Reached by the Star, Pennachetti said he was relying on Keesmaat, Byford and their teams to come up with the recommendations in the report. As for the ridership number, he said: “I don’t have an explanation for that number because it was a transportation planning key issue to determine.”

By July 9, staff had a working draft of their report to council. A copy obtained by the Star shows that language warning against the perils of a switch to a subway was toned done significantly in the final report.

For example, a line that said: “At present, there is insufficient information available at this early stage on the net cost of maintaining and operating a proposed extension of the Bloor-Danforth subway” was removed entirely.

There were also several additions to the final report.

An entire section on ridership projections, focusing on the 14,000 figure, was added.

Importantly, this line was included in summary: “TTC staff have identified that either an LRT or subway can effectively serve the Scarborough RT transit corridor. Each technology option offers distinct advantages.”

On July 10, Keesmaat emailed Pennachetti with the subject “Subway vs LRT” to offer more evidence of the LRT’s benefits.

“Are you aware that the LRT travels through 3 priority neighbourhoods and the subway travels through one?”

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“Are you aware that this will double the city’s debt — the cost is 3 billion?”

Pennachetti appears to not have responded by email.

The next day, Keesmaat emailed Councillor Josh Matlow’s senior policy adviser, Andrew Athanasiu, who had asked for information to support an opinion piece he was drafting to send to the Star. Matlow had been strongly opposed to the push for a subway from the beginning.

Keesmaat told him they were still working on the report to council, due the next day, and that it had been a “significant negotiation around the table.” She wanted to know what kind of material he needed.

Athanasiu responded that the piece had already been submitted. “That’s fine,” he said. “There’s an embarrassment of riches as to why this is a bad idea.”

“It is an embarrassment of riches,” Keesmaat replied. “It is a significant overbuilding of the needed infrastructure.”

She also noted the cost for a subway, as spelled out in the report, would be “mind boggling” — much higher than anticipated.

“Has this changed Joe P’s mind at all?” Athanasiu asked, inquiring about the city manager.

Keesmaat didn’t answer that question in her subsequent email.

Emails also show that in July staff were monitoring Keesmaat’s tweets and printing them out for her superior, Livey, to see.

In an email this week, Livey said: “Since I did not access Twitter regularly, I asked staff to print them for me. Staff regularly receive media and social media updates/clippings from strategic communications to help better inform us of the coverage on topics of high interest to the public.”

When the report was finalized, the recommendations were not at all what Keesmaat had earlier envisioned.

Instead, it gave council a choice, presenting the subway and the LRT as potential equals, with some caveats. In doing so, staff told council to choose instead of making a firm recommendation as the original outline had done.

The 45-member council convened on July 16 to discuss the report and make a choice.

It wasn’t even close. Council voted instead to build a subway, 28-16 (one councillor was absent).

The subway was again confirmed in a subsequent vote in October, which approved a tax increase to help cover the more than billion-dollar increase in costs. In the years that followed, Keesmaat worked to create a compromise that Mayor John Tory, who campaigned on building the subway, and his allies could support.

It involved reducing the number of stops from three to one and pitching that the savings could be used to build an extension of the Eglinton Crosstown LRT to the University of Toronto’s Scarborough campus.

In presenting the idea she argued an “express” subway — a favoured term of Tory’s — could be beneficial in the context of a network plan.

But since that plan was unveiled, mounting costs related to the subway have meant the funds already set aside may not even cover the cost of the subway, let alone the LRT.

And a recently published study on the subway estimates that in 2055, trains will still be two-thirds empty at rush hour — which would mean steep costs for the city to operate it.

Announcing she’ll decamp from her post at the end of September this year, Keesmaat will be long gone before any of it is hashed out at council and construction green-lighted.

At that July debate, Matlow, fighting to keep the LRT plan in place, asked Keesmaat to address the bigger question directly, out in the open. Which would be better for the city?

Keesmaat, on her feet in the cavernous council chamber, tried to make it clear.

“Based on the criteria that we have for great city-building, looking at economic development, supporting healthy neighbourhoods, affordability, choice in the system, the LRT option is, in fact, more desirable.”

“I just want to make sure that my colleagues heard that,” Matlow said as his time to question ran out. “So, you’re saying that all of the evidence-based criteria that you’re using, the LRT for this specific route is the preferred option for Scarborough and Toronto.”

“That’s correct,” Keesmaat said.

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