Just prior to the end of the Thrawn Crisis, Bail and his other siblings, Jaina and Jacen, were born to Leia Organa Solo and Han Solo. Because Grand Admiral Thrawn had promised to apprehend the triplets and their mother in exchange for Joruus C'baoth's help, Bail, Jacen, Jaina, and their mother were the targets of three unsuccessful kidnapping attempts by Thrawn's Noghri Death Commandos. After the triplets were born, prior to the deaths of Thrawn and C'baoth, Imperial Intelligence agents staged one last unsuccessful attempt to apprehend Leia and the triplets.
Following Luke's advice on protecting the children from the dark side of the Force, Han and Leia sent Bail, Jacen, and Jaina to New Alderaan and were placed in the care of Leia's lifelong friend and aide Winter. For more than the first year of their lives, Bail, Jacen, and Jaina saw their parents only twice. But any safety that could be derived from this arrangement would be short-lived. The reborn Emperor Palpatine discovered the location of the planet and ordered an attack immediately. During the chaos of the Second Battle of New Alderaan, Bail, Jacen, and Jaina were nearly kidnapped by Dark-siders Xecr Nist and Kvag Gthull, but their efforts were thwarted by the actions for Rayf Ysanna.
Following the battle, Bail, Jaina, and Jacen were brought to the ancient space city of Nespis VIII, where their parents and uncle discovered that the New Republic had survived the destruction of Da Soocha V. After the birth of their younger brother, Anakin, Bail, Jacen, and Jaina would live with their mother and father in the space city until they fled with the rest of the New Republic forces, shortly before the city was destroyed by one of the Galaxy Gun's warheads.
Heeding Luke's advice, Han and Leia took Bail, Jaina, Jacen and Anakin into hiding on the world of Onderon so that the future of the Jedi would be protected from Palpatine, who planned to spiritually enter Anakin and free himself from his last clone body, which was deteriorating at an alarming rate. The triplets and their younger brother would visit Onderon, a planet that had been presumed to be safe from Palpatine.
This proved not to be the case when Palpatine arrived on Onderon, hoping to spiritually enter Anakin. Bail, Jacen, and Jaina could do little but look on as their parents and uncle, as well as Empatajayos Brand battled Palpatine's last known clone. Palpatine was unsuccessful, but the incident led to Bail, Jacen, Jaina, and Anakin being sent to the world of Anoth with Winter.