Boris Cherkassky: a tribute to Leaside’s ultimate crossing guard – and friend

Crossing guard, Boris Cherkassky stops traffic at Millwood and Bessborough for St. Anselm’s student Chris Karnay Gayowsky.
Crossing guard, Boris Cherkassky stops traffic at Millwood and Bessborough for St. Anselm’s student Chris Karnay Gayowsky.

The outpouring of warmth and affection following the news of the sudden death of Leaside crossing guard Boris Cherkassky shows the high regard in which he was held by the children and families he helped to keep safe every morning and afternoon.

Boris suffered a heart attack while cycling to his post at Millwood and Bessborough on Friday morning, September 16th.

“This is a great loss to the St. Anselm School community,” said Principal Richard Walo. “Boris was loved by all the children and their parents, and always went above and beyond to keep everyone safe.”

Boris Cherkassky was born in 1948 near Minsk in the former Soviet Union and moved to Moscow as a child. He obtained a Masters degree in Mathematics and worked as a computer programmer. He and his first wife, Yulia, had two sons: Dmitry (Dave) and Yakov.

After seeing his Jewish friends persecuted by the KGB, he sought and received permission to leave the USSR and was granted asylum in Canada where he and his family settled in 1981. Boris worked for Sears, IBM and other companies in Toronto, and upon retirement from full-time work became a crossing guard.

Boris loved outdoor activities like cycling and cross-country skiing. He was particularly fond of kayaking in Georgian Bay near Beausoleil Island.

After Boris and his first wife Yulia divorced, he married Melanie Wilkens. “Boris loved his job and looked forward every day to his time at Post #5,” said Melanie. “He was so proud to do his part for the community. For him, it wasn’t just a job, it was almost a calling. And it was the people who made up his crossing guard community that were most important – getting them safely across the street and chatting briefly with each of them to catch up on their lives or give them safety advice about biking or crossing the street.”

In addition to his wife and ex-wife, two sons and four grandchildren, Boris Cherkassky is also survived by his mother, Maria Borodulin.

Principal Walo arranged for a memorial mass to be held at St. Anselm Church on Friday, September 22, following which the children were to plant a tree in his memory on the grounds of the school.

The principal also invited members of the St. Anselm community to submit tributes to Boris.

A special thank you to Richard Walo for his invaluable help in gathering the information and tributes from the St. Anselm community, without which this story could not have been prepared.”


Tributes to Boris

“Boris made the start and end of the school day better. It was his personal connection with all of us that was so special. Every day, he greeted us all by name with a big smile – children, parents, even dogs. He’d ask after any child he noticed missing from a family’s entourage. Somehow among those quick crossings each morning and afternoon, we got to know each other. He had a great place to go outdoor skating with his grandsons, he loved James Bond movies, PA Days (which he said stood for ‘Play All Days’), ice cream, and just recently – ping pong! He made us feel cared for. We will miss him so much.”

– Caroline Craig, Merton Street


Boris recognised for his community service in 2014 by former city councillor John Parker
Boris was recognised for his community service in 2014 by former city councillor John Parker

“Every morning when I parked my car on the street and walked towards the school Boris greeted me with a big smile and the line, ‘Have great day, sir.’ I always responded, ‘Have a great day yourself, Boris.’ One morning it was different. He stopped me without a smile and said, ‘You might want to look back, sir.’ I did and a heavy tree limb was hanging by a thread directly over my car. I never would have noticed that. I thanked him and re-parked my car on the other side of the street breathing a sigh of relief. All day I was thinking what a great guy he was. Yes, he was.”

– Derek Figiel, Music Teacher


“Boris was a very special man and will be greatly missed by me and my family. When Boris first came to the corner of Millwood and Bessborough, we were living just a couple of houses away. Nonetheless, we were running late to school nearly every day. Besides crossing us safely, Boris always had a smile and encouraging words for us. We got to know each other quite quickly. When we were packing up our home in preparation for moving, Boris noticed a kayak on our lawn. Later that day, at the corner, Boris said, ‘Tracy, I see you have kayak. I also have kayak. I am thinking to give it to you.’  He told me of the many wonderful adventures he had had with his family and that kayak, and that he would like it to be used again for more adventures. I accepted and treasure the gift. Such a kind and thoughtful man. I’m so sorry he is no longer with us.”

– Tracy Gaffney, Bennington Heights Drive


“My daughter Maran was very upset at the news. The children’s safety was paramount to Boris, and as Maran said, ‘He saved us every day from being killed; who will do that now?’ She is right. Daily he watched over all our children (and us), and he cared about them all and took his job very seriously, even with his ‘Welcome to Post #5,’ which is what he called his spot.”

– Bronwyn Gray, Leaside Park Drive

“I want to thank Boris Cherkassky for being a fierce and loyal protector of our children, handling the busy and dangerous intersection of Bessborough and Millwood with skill, care and friendliness. I never saw him miss a single day on that corner. In fact, I recall walking to school with my son on the morning of a wild snowstorm which had forced the cancellation of school buses. The streets were deserted, and we were not even certain that the school would be open. However, as we approached the crosswalk, I said to my son, ‘Look, Boris is actually there,’ to which my son replied: ‘Oh come on, please! Of course he’s there – Boris is amazing!’ Boris will be missed by everyone at St. Anselm Catholic School. I truly hope that Boris realized how important he was and wish his family to know just how much our community respected and valued his dedication.”

– Susan Karnay, Airdrie Road


“Some memories of Boris from my Grades 2 and 3 students: Charlotte D. remembers that Boris used to give her stickers when she crossed the street. Meara M. remembers that her dog Toby used to always run up to him every morning. Marigold O. said he always had treats for all the dogs. Ester N. and Eamon P. said that Boris always had nice compliments. Johnny R. said he always gave the kids high-fives, and Giacomo said he’s a great man. Elise P. said he always made her smile. Eva L. remembers that when Kate’s mom Michelle injured her foot, he gave her a get-well card. Mikaela & Gabrielle L. shared their favourite saying from Boris: “Single file, elephant style, facing traffic all the while!”

– Angela Napoli, Grade 2/3 Teacher at St. Anselm School


Memorial tribute honouring Boris
Memorial tribute honouring Boris

“Boris helped our kids get safely to school, so they could get an education, to prepare them for life. What we may have taken for granted along the way was the education Boris provided us everyday, even before entering school. Boris taught us some very important lessons in life. Important lessons about work ethic: Rain, shine, sleet, polar vortex, heat alerts, you name it, Boris was there and properly dressed. He rarely missed a day, and if he did he would let us all know. Boris taught us about the importance of a smile and a friendly face, of having a sense of humour and the importance of great colourful socks. Most of all, Boris taught us that small things matter. The way you treat those around you, even strangers, every day matters. Boris, you kept us safe for many years. You touched an entire community with one wave of your hand and the everlasting smile on your face. You knew each one of us by name and we will never forget you!  Rest in peace, Boris.”

– Alyssa Macedo, McRae Drive


“I first met Boris when my daughter Isabel started Junior Kindergarten at St. Anselm. On our first day, Boris introduced himself and since that day, Boris was a part of our life. I will always remember during that first year, Boris looking right into my eyes and saying to me ‘Mummy, you are doing something right’. As a new(ish) mom, what higher compliment can you bestow? He had this way of making me smile every time I walked into school. And I mean every time. Boris would laugh as my daughter updated him as to who she was having over for a playdate that day or what she was going to be up to on the weekend. He was her friend. I like to think Boris had a special soft spot for Isabel, but it occurs to me that this is how he made everyone feel. Today as I found myself helping children cross the street, I was reminded again what an important service he provided to all of us. It took four of us to do the job he did on his own. There were times when Boris, even after blowing his whistle, came between me and my children as cars would not stop in time. He made all of us feel safer. Boris, you will be so missed, my friend. We love you and thank you.”

– Maria Wilson, Airdrie Road

About Allan Williams 37 Articles
Allan Williams is a regular contributor to Leaside Life.