Interview with Mom’s Choice Award-Winner Chesand Gregory

Chesand "Chessi" Gregory, parent's pick author

Mom’s Choice Awards is excited to announce another post in our interview series where we chat with the inventors, designers, publishers, and others behind some of our favorite family-friendly products.

Hello, Mom’s Choice readers! Welcome back for another interview in our ongoing honoree interview series! For this interview, we were able to speak with Chesand “Chessi” Gregory, author of the MCA award-winning book Did Santa Wear A Mask?. Did Santa Wear A Mask? is a magical adventure about two brothers who are on a quest to help Santa save Christmas! Did Santa Wear A Mask? is a book that is sure to get your little ones into the holiday spirit, while incorporating the ongoing pandemic in a way that is both relatable and entertaining. You and your little ones are not going to be able to put this book down! Keep reading to find out more about Chessi and how she brought her unique children’s holiday book to life!

MCA: Hi Chessi, we are so excited to get the opportunity to sit down and chat with you today! Did Santa Wear A Mask? is such a sweet story that does a great job of addressing a time that has been very difficult and confusing for so many in a fun and uplifting way. Can I first start the interview off by having you tell us a little bit about yourself?

Chesand "Chessi" Gregory, author of the MCA award-winning book Did Santa Wear A Mask?

Chesand “Chessi” Gregory, author of the MCA award-winning book Did Santa Wear A Mask?

Chessi: I am Chesand “Chessi” Gregory, a multitalented, resourceful, and naturally charismatic teacher, wife of a scientist, and mother of two energetic boys. The JAG Brothers. When I am not teaching, I am most likely singing, crafting, gardening, or cooking up a storm for my family.

My personable and communicative nature allows me to easily captivate young minds by engaging them in fun and exciting ways where learning is achieved without their awareness. My mission is to foster confidence in families by teaching them fun and engaging parenting strategies to help them raise and empower the leaders of tomorrow.

As an educator, I have received The Ken Grey Award for Innovations in Teaching and The Edna Scott Award for the Greatest Degree of Diligence in Teaching. And as a lifestyle model, I have been featured by the American Girl® Doll Company, Body Glove®, Leg Master®, and Loblaws.

MCA: Congratulations, those are quite the accomplishments you’ve had! What lead you on your path from a teacher to eventually becoming a writer?

Chessi: Becoming a writer was very fulfilling. There were a lot of moments that I enjoyed including moments that reminded me to believe in my vision. My publisher didn’t believe in my vision which led me to pursue it on my own. Today the vision included in my book that my publisher didn’t believe in has been endorsed by one of the world’s top retailers, Amazon. My children inspired me to create the award-winning book, “Did Santa Wear A Mask?”

MCA: Did Santa Wear A Mask? is a holiday book that is sure to give anyone who reads it the “warm and fuzzies,” but it also tackles the current climate we are in with the coronavirus pandemic in a fun and uplifting way. How did the idea of Did Santa Wear A Mask? come to be?

Chessi: Did Santa Wear A Mask? was inspired by my four-year-old son, who, during the onset of the COVID-19 pandemic in early Spring, asked me, “Mommy, will Santa wear a mask?” His question may have sounded simple, but it showed just how far ahead he was thinking about the mask mandates impacting his favorite holiday. I was stunned and instantly realized how much we underestimate how brilliant the mind of a child is. I decided to write this book in response to his question and to showcase how important it is to empower the voices of our children.

MCA: They do say that some of the best ideas come from thinking like a child! What are some of the key lessons found in Did Santa Wear A Mask??

Chessi: In addition to demonstrating the impact a child’s voice can make while helping preserve the Christmas tradition during the COVID-19 pandemic, the story includes many teaching points and memorable Christmas song references embedded throughout the text.

The songs help to preserve pleasant memories of time-honored Christmas traditions for readers. At the same time, the story emphasizes teamwork, empathy, and the interior and cover illustrations promote inclusivity and reflect the diversity of those celebrating Christmas around the world.

MCA: Did Santa Wear A Mask? features the adventures of Jali and Jax, or the “JAG Brothers” as more commonly known. Tell us more about the JAG Brothers and how they received their moniker!

The "JAG Brothers" Jali and Jax.

The “JAG Brothers” Jali and Jax.

Chessi: My sons share the same initials, JAG, so I used that fact to create the JAG Brothers. In 2016, the superhero capes seen were designed by my elder son with their favorite colors, green and yellow. I incorporated the capes in the story to empower other children. I believe every child deserves the right to be heard, to share their thoughts and ideas, and even feel like an everyday superhero.

MCA: We couldn’t agree more! Your book has received so much positive feedback since its original publication last December. Can you share with us some of that feedback?

Chessi: The response from readers has been very inspirational. Here are some of the feedback we have received:

Great product overall! Great story with relatable characters. Book quality was also great! I will be recommending this book to friends and family. I would love to give it as a gift.– Elyse, MD / USA


My 5-year-old really enjoyed this book. It normalized Santa in this new normal world. My daughter asked if Santa has to wear a mask when bringing presents earlier in the year, so this book helped to calm her nerves about Christmas and Santa. We really enjoyed reading it together and it may be a new tradition to read every year

-Kathleen, ON / CA


The narration is straightforward and realistic. One of my favorite quotes is on page 17: “It’s ok, Santa, don’t be sad. I know Christmas this year is different,” said Jali in a comforting voice.” Those words pulled at everything inside me, nearly bringing me to tears.

-Readers Favorite, USA


Our panel of judges felt this book merited a place on our list of the best in family-friendly products that parents and educators can feel confident in using.
– Dawn Matheson, CEO of Mom’s Choice Awards

MCA: If you could ensure readers of your book walk away with one main lesson, what would it be?

Chessi: “Alone, we can do little, together we can do much.” This well-known quote from Helen Keller has undoubtedly moved me when writing “Did Santa Wear A Mask”. As an award-winning educator and advocate for children, one main lesson from the book is to amplify children’s voices. I also find that Helen Keller’s quote embodies my mission to inspire and empower families to embrace and raise socially conscious children.

MCA: Thank you for leaving us with such a wonderful message and a great interview! Please be sure to keep us posted with all the future adventures of the JAG brothers! 

You can learn more about Chesand “Chessi” Gregory and her award-winning book, Did Santa Wear A Mask?, by visiting her MCA Shop pages.

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Interview With Chesand Gregory

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