It is known that in February 1378, he arrived in Prussia and participated in the Galicia–Volhynia Wars, during which time he was made a knight of the Teutonic Order.
[1] He returned to Italy in 1381, getting involved in the dispute between Louis I, Duke of Anjou, and Charles of Durazzo over which of them would succeed Joanna I of Naples after she was excommunicated for supporting Antipope Clement VII.
His position as Mary's husband and thus the dominus of the County of Lecce allowed him to reclaim Soleto from his brother, officially becoming the Count upon his father's death in 1399.
Additionally, over the years, he received numerous possessions and titles, many in the Terra di Otranto region.
Despite his many years of service to Louis's family, Raimondo knew he was allied with the losing side, and switched allegiances once more on the promise that he would be given the Principality of Taranto, which happened in April 1399.
[1] Raimondo is buried at the church of Santa Caterina d'Alessandria in Galatina, which he had commissioned,[1] together with his son and heir Giovanni Antonio.