Jackson Holliday’s sister, Gracyn, dressed up for the high school formal winter event on Monday. Gracyn posted a photo dump on Instagram featuring her in a black short dress."Allll dressed up," Gracyn captioned the post. View this post on Instagram Instagram PostHolliday’s mother Leslee shared a carousel to cheer her daughter. The post includes a mother and daughter close-up selfie. Another photo features 4x Silver Slugger and former Yankees hitter Matt Holliday standing closely while Gracyn held a small bouquet. The last snapshot features the Holliday clan, including Jackson, Ethan and Gracyn.Leslee wrote a heartfelt note in the comments section."Winter Formal for our girl! Love you G. Daughters are the best!!" Leslee wrote.Gracyn expressed her gratitude,"Love you mommy."Jordan Sprinkle’s wife, Alyssa, also reacted to the post."So cute!!!" Alyssa wrote.Former Baltimore Orioles player John Means’s wife, Caroline, reacted,"😍❤️ Pretty girl!!!"(Image source- Leslee Holliday/Instagram)Jackson Holliday’s wife Chloe dropped a two-word reaction on Gracyn's post.Gracyn posted a photo dump of her cheerleader session on the field on Instagram on Nov. 29. The photos were a sneak peek of her college football season as a cheerleader. She wore the Stillwater High School Pioneer football team cheerleading uniform."✌️ out fb season," Gracyn captioned.Jackson Holliday’s wife, Chloe, adored her and wrote,"so cute."(Image source- Gracyn Holliday/Instagram)On Nov. 8, Gracyn celebrated her sixteenth birthday, as her father Matt Holliday shared a post to wish her. The post highlights a blurry image of Matt hugging Gracyn."@gracynholliday is 16. I’m not gonna get into how special she is because I don’t feel like crying lol. She’s such a light in this world. Can’t wait to see what God has in store for you. Love you sis," Matt captioned the post.Gracyn commented on the post,"I love you so much 🥹."(Image source- Matt Holliday/Instagram)Gracyn also commented on Chloe's latest post on Nov. 9, writing,"cute & aesthetic & sweet."(Image source- Chloe Holliday/Instagram)Jackson Holliday is the elder sibling of two younger siblings, Ethan and Gracyn. Ethan is also a promising young baseball player and a top pick in the 2025 MLB Draft for the Colorado Rockies.