[2][3][4] Since Tancred had many sons, and his possessions weren’t enough to satisfy all of them, Humphrey and many of his brothers were soon forced to seek fortune elsewhere.

[5] Goffredo Malaterra and Amatus of Montecassino record that Humphrey journeyed to Southern Italy with his brothers William Iron Arm and Drogo, around 1035/7, to strengthen the ranks of Rainulf Drengot, Count of Aversa.

In 1048, during some hostilities between Normans and Byzantines, Humphrey also conquered Troia and Vaccarizza, and he helped his young half-brother Robert Guiscard, who had just arrived in Southern Italy, to settle down.

Robert Guiscard, the hero of Civitate, meanwhile conquered Minervino Murge, Otranto, and Gallipoli, before Humphrey sent him back to Calabria in fear of his growing power and influence.

Humphrey married Gaitelgrima, daughter of Guaimar III, whom Amatus of Montecassino calls a sister of the Duke of Sorrento.

[6][7] Humphrey and Gaitelgrima had four sons: We also know that they had a daughter, as Amatus of Montecassino records that Robert Guiscard pursued "Abelard and Gradilon, the husband of his sister" after the former's rebellion in 1078.