More than a mentor: Barbara Caplan, December 5, 1944 - November 13, 2023
Thirty-three years is a long time to be mentored by someone. But not long enough — I wasn’t ready for the news that my work mother died on November 13, 2023.
Barbara Caplan held the top job in the city bureaucracy, City Clerk, when I started working at Toronto City Hall in September 1990. She was the first woman in the role and she laughed when she told the story of how one councillor asked her what a woman just in her 40s would do with all that money. Barb, however, was not there for the money. Barb was there to facilitate good public decision-making, apolitically and efficiently.
Hers was the department I was hired into as a management trainee. Barb had no hand in choosing me, but I ended up working in the elections section where, as Clerk she was also Chief Returning Officer. I was tucked into an office on a hall next to the back staircase where Barb would dart regularly down to the underground parking for a smoke.
Whether she saw something of herself in me - I like to think so - or whether she appreciated my irreverent and often inappropriate sense of humour, we soon became smoking buddies. Standing beside Barb with my lit menthol B&H in hand, I became privy to things I wouldn’t have otherwise learned and we got to know each other. I gave up the habit years ago, although Barb struggled with the tobacco addiction her whole life.
Barb identified opportunities for my professional development within her department and by 1994, I was the Manager of City Council, a role where I worked closely with her and the Deputy Clerk, Syd Baxter, also still a good friend. I managed the team that prepared agendas, attended the meetings, and made sure Council’s decisions were documented and disseminated accurately and promptly. Those who’ve worked with me since will know of my obsessive need to achieve all these things with every meeting I organize. That’s all Barb’s influence. Barb knew that preparing the agenda and the minutes shapes the way issues will be discussed and remembered, a significant and important role that should never be under-resourced.
It was a different time. No-one ate lunch at their desks. Indeed, Barb would take a stack of “seat work” to Barberians, a steakhouse on Elm Street, a 10 minute walk up the street. (To be clear, the restaurant wasn’t named after her - that was purely coincidence!) Barb was driven in the fleet car that was hers to use personally in off-hours. Not fancy - a Ford Taurus, as I recall - but being driven at lunch made sense because walking would have taken away from her time ploughing through the documents she had to review each day. If you had letters in that pile for her signature, you knew they would come back with edits. She championed the plain language movement at City Hall and was particularly proud of her campaign to eliminate Latin holdovers from the minutes.* If she couldn’t find syntactical changes to make, she would most definitely add or move commas. We mocked her mercilessly about it. But she never stopped. I am a better writer because of Barb.
Sometimes Barb would take one of her team to Barberians for lunch. I had the honour only once. She greeted all the restaurant staff by name and inquired about their families. They treated her like royalty. We sat in her private dining room and ate steak. There were likely martinis.
Another lunch I strove to be at was the annual “perfect attendance lunch,” Barbara’s reward for those who never took a sick day. Unsurprisingly, it was a small group of the childless, as Barb was herself. Barbara identified strongly as a feminist, but today this lunch would be seen as discriminatory against women, often the primary caregivers, not to mention badly out of step with a COVID world. Then, perfect attendance was something I aimed to achieve, not just to have lunch (although that was certainly a factor) but to match Barb’s strong work ethic.
Once, Barb held an all-day meeting at her house at 77 McGill. I was invited to participate with Christine Dodds, the Executive Committee Secretary, and Ina Robinson, the Assistant Executive Committee Secretary.** We spent the day reviewing a proposed revision to Council’s procedure by-law, the stuff of nightmares for many but of dreams for us. I was a bright-eyed 27 year old who likely knew nearly nothing. We knocked off for lunch and Barb cooked us something scrumptious which we ate on the backyard deck with wine and cigarettes. That day I experienced how you mentor and treat staff with respect and kindness, while weaving personal and professional lives together. It is one of my fondest and most formative professional memories.
It was no secret Barb had a progressive political streak. Her second husband was Gerry Caplan, a provincial NDP strategist; Google her and you’ll find the photo of her, Gerry, and Stephen Lewis, the NDP leader in the early 70s and the best man at their wedding. But under Barb’s leadership, we were driven by impartiality. No councillor, regardless of their stripe, could be seen as being favoured over another, despite our many backroom laughs or strategy sessions about handling difficult members. It was only when right-winger, Michael Walker, threatened to harm Barb physically that she took action. Her 1992 complaint to council resulted in a code of conduct for city employees and council members in the workplace, something that hadn’t existed before. I’m not telling tales out of school - this was reported in a Toronto Life article in 2010.
When the province amalgamated Toronto with its neighbouring municipalities in 1998, Barb retired and I moved on too. But Barb never let go of her role as my mentor. She was a reference for me in my law school application and for every job I’ve applied for since, including earlier this year. She has also been the glue that bound together staffers from the pre-amalgamated city through different groups she convened for meals. I was part of an intimate group whom she called “The Usual Suspects.” We met two or three times a year at Le Paradis, a French bistro in midtown. I have fond memories of teasing Barb while she divided up the bill by hand in her confident handwriting on our red-wine-stained paper table cloth. With COVID lockdowns, we couldn’t meet in person. I missed the connection and began hosting Zoom meetings of the Usual Suspects. I think Barb was grateful to have passed the organizing torch to her protege, at least I hope so. Her other group, the ExPats, had its regular monthly lunch last week and a dozen or so of us raised a glass in her honour. They will continue to meet, but it won't be the same. The Usual Suspects, the ExPats, and many, many others benefited during early COVID, with Barb’s daily digest of funny emails people had forwarded to her. That daily connection and the humour they contained helped us all feel a part of something bigger despite the fact many of us were COVIDing alone. That glue again.
I was honoured to be among a handful of her staff who attended Barb’s wedding on the occasion of her 25th anniversary with her partner, Michael. It wasn’t until I met Jack, though, that my personal relationship with Barb and Michael strengthened. It was so fun to listen to Jack and Michael laugh about how similar their partners were. In fact, they were also very alike! Barb and I both understood the charm of being with someone who was our opposite - like Jack, Michael didn’t fit the mold. They were great together though and when he died seven years ago, a piece of Barb’s verve for life died with him.
When Jack was treated for cancer, he and I often hung out with her at her condo between appointments. Despite my disapproval, she and Jack would slip into her sunroom for cigarettes and laughs - they both claimed they wanted to quit, but shrugged when I asked when. When Jack and I decided to elope during treatment, Barb was an ideal choice to be a witness. We both loved her and she was neutral - neither in Jack’s family nor mine - and therefore was less likely to offend anyone. She made that trip back to City Hall all the more significant for me. I will cherish the memory of being at the restaurant, One, at the Hazelton Hotel as Barb and Jack’s aunt and uncle, our other witnesses, lingered with Jack and me over a champagne-infused lunch, a break from the stressful tedium of the cancer treatment schedule.
When Jack’s illness ramped up, Barbara was one of my strongest supports. Once when I shared with her that being his caregiver was the most important thing I’d ever do, she corrected me: “Being his caregiver is the most important thing you’ve done - yet.”I’ve reflected on her words many times since Jack’s death. She was right - there is more left for me to do.
Barb was an early subscriber to my blog and I could count on her to comment and encourage my writing. Her last email to me was a response to my survey of people close to Jack and me about his MAiD death. Barb believed strongly in the right to choose to die and had shared my writing with many in her circle. Her response to my survey was prompt, succinct, and clearly written with properly placed commas, just as I would expect. She told me one of her friends had died with medical assistance and my writing had helped her family understand her decision. Barb concluded her comments by thanking me for keeping the MAiD discussion going. I am grateful for her support.
Barb’s physical health had started to deteriorate in the last year but I was thrilled when she and our mutual friend, Peter, made a trip to Chandlerville on October 22 for lunch. Although I’d heard she’d been using a walker, she came into my house unaided. Peter and I watched with breath held while she navigated my stairs, determined as she was to see the 2nd level. She signed my guestbook in handwriting that reflected the frailty she was desperately fighting, telling me my place would be “a glorious retreat/nest for many years!” These are even more precious words now. We had such a good time that day, laughing and drinking wine. She left with a jar of my squash soup in hand, a hug, and a promise that we’d get together soon.
If you’d like to read Barb’s obituary, click here. Barb’s charity of choice was Homes First. Click here to donate in her memory.
* Barb claimed she had buttons made that said “stamp out viz.,” a Latin term to preface a list of examples. We later replaced “Whereas" with “Because” in Council resolutions, a radical decision that rocked the boat for some!
** Barb is the last of these three great women to die. Ina died of Creutzfeldt-Jakob disease in 1999 and Chris of cancer in 2003.
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