Award-Winning Author, Chesand Gregory Inspires Families Through Pandemic with Christmas Adventure Book

Chesand Gregory, an award-winning author, educator and successful entrepreneur, is preparing for the launch of her new book, “Did Santa Wear A Mask? A Christmas Adventure with the JAG Brothers”. The launch will take place virtually on Saturday, November 6, 2021.

Awarded the Mom’s Choice Gold Award, which honours excellence in family-friendly products, the book was created to answer questions about the COVID-19 pandemic posed by the author’s younger son. In response to her son’s curiosity, Chesand penned a book that addresses the pandemic’s safety measures in a way that children can easily understand.

With this book, Chesand embarked on a mission with her two sons, the JAG Brothers, to positively change communities and empower children’s voices. Through proceeds from this book, Chesand and the JAG Brothers will continue to support the Helping Hands Jamaica Foundation’s ongoing goal to build schools in rural communities in Jamaica. Proceeds will also be donated to the Toronto Foundation for Student Success in Canada, which provides immediate educational support to children in need.

As a passionate activist for children’s rights, Chesand works towards inspiring children to make a difference. In this award-winning book, she creatively introduces the JAG Brothers as they help Santa solve one of his biggest challenges during the pandemic. Through her innovative strategies and the new superhero characters, Chesand displays to young readers the importance of teamwork, cooperation and problem-solving. The story also encourages children to celebrate their individuality while embracing inclusion and diversity.


Chesand Gregory is a successful educator, wife and mother of two, who flourished into entrepreneurship in 2015. As the founder of JChess Designs, she created her own line of breastfeeding covers to provide nursing mothers with privacy in public. On the heels of this success, Chesand authored her current book “Did Santa Wear a Mask?”. She continues to improve the lives of children through other initiatives and as a donor to multiple charities. Like Helen Keller, Chesand believes that “together, we can do so much more.”

For more information, visit or @authorchessi on Instagram.

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