Tradition, Diversity and Safety – All Things That are Joyfully Tied Together in Chesand Gregory’s Children’s Book, Did Santa Wear a Mask.

Published on January 7, 2021

One may not relate Christmas traditions with safety, but this past year has presented us with many other surprises, so it may be par for the new normal course, so to speak.

In an effort to reflect diversity and promote inclusivity, Chesand Gregory has written a delightful book, inspired by her 4-year-old son, who innocently asked if Santa would be wearing a mask during Christmas. The book was further inspired by her family, The JAG Brothers, wanting to preserve Christmas traditions, while keeping individuals, and of course Santa, safe during and after the holidays. Due to the challenges of a worldwide pandemic delaying her book’s release, Chesand was forced to adapt by changing her book’s original title. Now, Did Santa Wear a Mask, releasing January 2021, brings to light concerns about incorporating lifelong customs into a space where new safety guidelines are a must.

Author, Chesand “Chessi” Gregory is a trained high school educator with an expertise in nutrition and teaching experiences spanning Preschool, Elementary and High school. Her love of the arts led her to the study of Couture Designs and winning awards in music competitions in her early years encouraged her to become a contemporary singer. Gregory’s desire to write Did Santa Wear a Mask was sparked by her interest in utilizing both her artistic background and educational experiences to encourage best practices recommended by the WHO including wearing masks, washing hands and using sanitizing products to remain safe and healthy throughout the pandemic.

Gregory also wanted to convey the significance of maintaining family traditions from a child’s perspective. With the help of her illustrator Cleoward Sy, her brilliant narrative captures the essence of hope and the Christmas spirit in a way that relates to children across the globe.

Did Santa Wear a Mask integrates powerful educational components into the story in a light-hearted way that both children and families will enjoy. It explains the Covid-19 pandemic and reinforces best practices that will help stop the spread of the coronavirus. Teaching points included in the story revolve around hand-hygiene, science, sympathy for others, and teamwork. The cover’s artwork, featuring famous landmarks seen from Santa’s viewpoint, adds an aesthetic touch while lyrics of popular Christmas songs are embedded into the narrative to help set the atmosphere and initiate fun sing-alongs.

Recognizing that there is no pause button when it comes to educating children on the significant changes needed in order to safely move forward in our lives, Gregory’s mission is to utilize the opportunity of having a book to continue the teaching and learning process outside of classrooms, and communicate imperative lessons to children all over the world, that create awareness of hygiene and disinfection.

Presented in a fun, memorable story-like way, Did Santa Wear a Mask takes valuable information and translates it into a story that is relatable, regardless of nationality, gender, age or race. Gregory’s hope is to donate a portion of the proceeds from the sales of her book to Helping Hands Jamaica Foundation to give children a better future through education.

As a woman who believes in holding firm to dreams of any size, she was told early on that most established companies won’t allow new authors to use their trademarks, but because her project gave her such joy and fulfillment, she kept trying. Knowing that the worst she could hear was the word “No”, her persistence eventually paid off. Proudly, Gregory is able to share that Did Santa Wear a Mask will be available to more than 39,000 retailers including Barnes & Noble, Chapters, and Amazon. Amazon has also endorsed her book and was incorporated into the story with an interesting spin. To promote the book, Gregory’s innovative spirit again shines in the youtube video she created that is entirely fitting to the story’s theme and the setbacks she encountered.

While we adopt a much different way of living and celebrating, Gregory invites us to recognize the importance of remaining united as people of all ages, genders, nationalities and races fight against COVID-19. Did Santa Wear a Mask is a beautiful story that, despite necessary change, reinforces the importance of maintaining tradition and believing in the magic of Christmas.




Canadian based Chesand “Chessi” Gregory is a multitalented, resourceful and naturally charismatic teacher, wife of a scientist, and mother of two energetic boys; The JAG Brothers. When she is not teaching, she is most likely singing, crafting, gardening or cooking up a storm for her family.

Her personable and communicative nature allows her to easily captivate young minds by engaging them in fun and exciting ways where learning is achieved without their awareness. One of her goals is to continue moulding the leaders of tomorrow by writing children’s books to foster their growth and development.

Before writing her first book, Chesand was chosen by the American Girl® Doll Company to depict Melody’s mother in their book; Melody – No Ordinary Sound. She was also featured in the Loblaws® Celebrate your kitchen catalogue and as a lifestyle model for other well-known brands including, Leg Master® and Body Glove®


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