Chesand Gregory challenges COVID with Christmas book for children

Krysta Anderson
Krysta Anderson

December 21, 2020

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Will Santa wear a mask for Christmas? This must be a burning question on the minds of so many children worldwide. Chesand Gregory has presented this answer in a creative, storytelling fashion.

Her children’s book, titled Will Santa Wear a Mask? A Christmas Adventure with the JAG Brothers, features two brothers, eight-year-old Jali and his six-year-old brother, Jax.

‘Will Santa Wear a Mask? A Christmas Adventure with The JAG Brothers’ will be sold on Amazon, Chapters, and in over 39,000 other retailers.

“When they heard the breaking news that Santa closed his workshop as the coronavirus spread to the North Pole, they realised he may not be able to fulfil Christmas wishes this year,” the author told Flair.

Since these brothers enjoy helping others in need, they were determined to spread their Christmas cheer to Santa as well. So they set plans in motion to safely help him while keeping in mind the COVID-19 precautions reinforced by their parents. But, even with their help, Santa noticed he still had a big problem. So at the heart of the story is: what will Santa do this COVID-affected Christmas? As a bonus, the book is filled with famous Christmas songs and splashes of Jamaica’s vibrant culture.

Gregory says her two-year-old son inspired the concept for this festive book. “I wrote the book to help preserve the Christmas tradition for my children, as well as other children around the world, while keeping Santa and everyone safe this season,” the mother of two shared.

Wife, mother, entrepreneur, model and author of ‘Will Santa Wear a Mask? A Christmas Adventure with The JAG Brothers’, Chesand Gregory.

Influenced by her own experiences as an early-childhood educator in Canada, the Jamaican native believes that it was essential to not only spark imagination among these young minds at this critical time, but also to teach children, and emphasise to anyone reading the book, the importance of proper handwashing.

“Because the story is told from a child’s perspective, children and supportive families will learn and continue to do their part in stopping the spread of COVID-19,” she said.

Diversity and inclusivity were important for Gregory, as such the book is adaptable to children all around the world. There are several teaching points for parents and educators to utilise, making Will Santa Wear a Mask? A Christmas Adventure with the JAG Brothers both educational and festive.

On the artistic side, the writer remained integral in the creative task, pulling on her sewing skills to assist with the design. “He (the designer) was in need of some inspiration from me to design the main character’s mask. And I wanted an integration of where we came from, so I created a Jamaican-inspired mask that will be branded under my other business, the JChess Designs line of products.” The masks are available as keepsakes. Gregory says families will be able to wear it and represent where they are from, while teachers can use the variety of masks available to show students the different countries around the world.


Gregory could write about pandemic protocols in any season; so why in this one? For her, it’s simple: Christmas is the most wonderful time of the year.

“Christmas means a lot to me. On a scale of one to 10. It’s a 10 for me. I had a fun childhood growing up at Christmas time, and I wanted to ensure my children [do as well]. Christmas this year should be about reflecting [and making] memories that they will love and share with others, despite the pandemic. And I hope the book will help to rediscover just that.”

Writing brought Gregory a sense of solace and allowed her to reconnect with her supportive spouse, sons, and preschoolers, to some degree, while being subjected to lockdowns and other restrictions. “My family motivated me to utilise my teaching since I was unable to carry out a pragmatic approach to my duties due to COVID-19. It has been very challenging yet fun. I was able to bond a lot more with my family while working from home during the writing process.”

When the mother, entrepreneur, author and model is overwhelmed, she is comforted and reassured by this quote, “Never give up! No obstacle is impossible. There is always a way around adversity, no matter what. Keep believing in yourself.”

The book is set to be sold on Amazon, Chapters, and in over 39,000 other retailers.

Krysta Anderson


Krysta Anderson

Tackles sex and relationships with honesty and openness. For months, she took readers on a journey of self-exploration with personal dating column 'Single but Iffy to Mingle'. Now she's ready for an even bigger adventure.

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