Chesapeake Powhattan's Promise, nicknamed Squat, was born on Assateague and went through the Pony Penning auction. He was sired by Witch Doctor and out of Promise of Summer. Squat was bought by the Boysen family of Chapel Hill North Carolina. He received his nickname because he sat down in the auction ring and again when they were loading him on the trailer to go home. Squat was a stallion at the Boysen's Thousand Welcomes Farm and sired a number of foals for them. He was also broken to ride. Two of the foals he sired there are the mounted games and trick ponies Chesapeake Boomerang and Chesapeake Lightning. He also sired Surf N Turf who is a member of the Chincoteague Pony Drill Team.
Some years later Chesapeake Powhattan's Promise was sold to Kendy Allen and moved back to Virginia near his birthplace. He sired his first Misty descendant foal in 2015 the bay pinto mare Misty's Eye of the Hurricane out of Misty's Hurricane Izzy. Squat sired smokey black pinto mare Misty's Audra Rain in 2019 out of Misty's Icicle. Squat's last foal is bay pinto gelding Misty's Blue Morning, born to Misty's Morning Glory in 2020. He passed away after a short illness on September 26, 2020.