Leasiders who chose to go home again

The O'Learys.
The O’Learys.

You can’t go home again, as novelist Thomas Wolfe wrote. Or can you? We spoke to some Leasiders who did just that:

The O’Leary and Holt families

Courtney O’Leary and her sister Jessica Holt (née Moreland) grew up in North Leaside and attended Northlea and Leaside High School, graduating in 1996. They have fond memories of a safe and happy childhood when everyone knew everyone else and looked out for each other, often sharing parenting duties. Both moved back over the last 14 years and say their husbands have also grown to love the neighbourhood. In fact, Eamon O’Leary’s mother, brother and sister are now Leasiders, too, because as he says, they enjoy the feeling of living in “a small town within a big city.”


The Holts
The Holts

The three O’Leary children, Ruby (10), Marigold (9) and Kingston (6), all attend St. Anselm Catholic School, while the Holt girls, Olive (9) and Maude (7), go to Northlea.  Both sisters appreciate the dedication of the teachers and the excellent programs at the schools, as well as the variety of extracurricular activities available in the area. But, they would like to see an end to the current division between north and south Leaside resulting from the construction on Eglinton.

The Obrights

The Obrights.
The Obrights.

James Obright started out at Mrs. Park’s School and Bessborough, but switched to East York’s Presteign Heights and Cosburn Middle School for the gifted program before finishing at LHS and graduating in 1996. His wife, Kristie (née Morland), grew up in the St. Clair-O’Connor area, but graduated from LHS in 1997. James recalls fondly his involvement in sports and the “amazing” schools, but what he treasures most are true lifelong friends, many of whom live nearby and still get together regularly.

After James worked in London, England with RBC for two years, the Obrights decided to return to Leaside because of the proximity to downtown, his parents, the arena, parks and the library. They really appreciate these conveniences as well as the specialty shops and restaurants nearby.

Daughters Katherine (7) and Abigail (5) enjoy their classes at Bessborough and the “overwhelming” choice of extracurricular activities such as skating, swimming, circus school and dance.

The family’s only concern about life here is, as James says, “the impact of all the proposed high-density development on the character, traffic and community resources of our otherwise low-density neighbourhood.”

The Watters family

The Watters.
The Watters.

When Brad Watters moved to Leaside, he entered Grade 6 at Bessborough followed by high school at LHS. His wife, Lynda (née Duckworth), attended Northlea, then pursued French immersion at Glenview and Lawrence Park, before returning to LHS for her final year. There, at the same school her parents attended, she met Brad in my Grade 13 English class, and they went off to Western in 1988.

Both Brad and Lynda enjoyed the social aspect of growing up here with lots of children to play with, and the sense of closeness that comes from knowing everyone in the class. They chose to settle here because of proximity to family and friends as well as the area’s strong community spirit.

Their eldest daughter, Kaitlyn, is in third year at Western, Lauryn is in Grade 12 at Leaside, and Mark is in Grade 9 at St. Mike’s, a choice based on his talent for lacrosse. Their parents have high praise for all Leaside schools with their increasing parental involvement and the use of more differentiated strategies to engage the students. The Watters are happy their children are being well prepared for excellent careers while thriving in “a great community.”

Know of other Leasiders who have returned to the community where they grew up? Let us know at

About Janis Fertuck 108 Articles
Janis Fertuck is a retired English teacher who spent the last 30 years of her career at Leaside High School. She enjoys writing about the vibrant Leaside community where she and her husband have lived for 22 years. Her other favourite pursuits include a part-time job at a boutique on Bayview and volunteering with the Bayview Pixies.