Every year each of Twelve Contrade of Remora have a horsemaster in charge with planning and preparing the horse and the jockey who will participate in the Stellata. The horsemasters are addressed by the title of Capitano during the Stellata and will meet with the horsemasters of allied Twelfths to discuss strategy.
Outside of the Stellata, the horsemasters are responsible for breeding and racing horses to run in the Stellata.
- Paolo Montalbano, the father of the Ram's intended jockey, Cesare Montalbano, for the Stellata of 1578. Before the Ram's victory in 1578, he was the last rider to win the Stellata for the Ram.
- Riccardo, the Horsemaster of the Twins, hosts the Air Twelfths (the Scales and the Water-Carrier) during the strategy meetings for the Stellata. As the Horsemaster of the Twelfth affiliated with Remora, his Twelfth along with that of the Lady have won the majority of the Stellata races over the past fifteen years thanks to the influence of the di Chimici family. He is on good terms with the Horsemaster for the Lady.
- Edgardo, the horsemaster in 1578.
- Giusto , the horsemaster, in 1450, of The Crab. He is seen in A Sting in the Tail, talking with the horsemasters of The Scorpion and The Fishes.
- Emilio, the Horsemaster of the Lady hosts the Earth Twelfths (the Bull and the Goat) during the strategy meetings for the Stellata. He shares the same assessment with Enrico Poggi that the Ram's combination for the Stellata, Arcangelo and his rider, Cesare Montalbani, are strong competitors and will be the ones to beat. As the Horsemaster of the Lady, the Twelfth associated with Giglia, Emilio is on good terms with the Twins' Horsemaster, Riccardo; both their Twelfths have won the majority of the Stellata for the past few years thanks to the influence of the di Chimici.
- Arnolfo, the Horsemaster of the Lady in the short story Sugar Fox. Described as fat and warty-nosed man, he is an excellent judge of horses and happens to be fond of children, having a grandson about Donato Miele's age. The Lady's mount for the next Stellata is mentioned to be a bay stallion, Il Principe.
- Giovanni (1578), the Horsemaster of the Scorpion in 1578; he hosts the Water Twelfths (the Fishes and the Crab) during strategy meetings for the Stellata. He and his allies are the last to learn the secret of the flying horse that was born shortly before the Stellata that year.
- Antonio (1450), the Horsemaster of the Scorpion in 1450, the main character of the short story A Sting in the Tail.
- Martino, the horsemaster in 1578
- Orlando, the horsemaster of The Fishes in 1450. He is seen in A Sting in the Tail.
- Roderigo, the Horsemaster at the Ram's auxilliary stable in Santa Fina, where Merla is initially hidden in City of Stars and eventually resides on a permanent basis with her mother Starlight. He cares for the Ram's horses that are not currently being trained for the Stellata.