While Pompey's family was extremely wealthy it was not one of the ancient families that dominated Roman politics. Pompey's family was relatively from the plebeian rather than the patrician class; Pompey's father Strabo was the first of his family to become a senator. Strabo ascended through the curus honorum, becoming consul in 89BC. Plutarch writes that the Romans never hated any of their generals so much and so bitterly as they hated Pompey's father' (Plut.Pom.1). While Plutarch over-emphasizes it is apparent that Strabo was disliked by the citizens of Rome. He had the opportunity to march on Rome and took his army just outside the walls attempting to gain a second consulship. While considering his next move, Strabo's army was hit by a plague and Strabo died. According to Plutarch, the reputation of his father seemed not to affect the public opinion of Pompey, as he did not inherit his father's reputation, just his wealth (Plut.Pom.1)
The fact that Pompey's family was not one of the main political families in Rome was an advantage to him as he was considered an underdog for the people. While Pompey was wealthy, his roots were in the countryside. This enabled him to become popular with the people, particularly in the early stages of his career where he refused to accept too many honours and titles. However coming from a relatively new noble family disadvantaged Pompey as he needed political experience and serving under his father at such a young age kept him away from political life at Rome.
Pompey compensated for a lack of connections that his family background had left him by creating alliances through marriage. The first of Pompey's marriages was to Antistia in 86BC. After Strabo's death Pompey was put on trial for misappropriation of public funds. The presiding judge of the case was Antistius who was praetor at the time. Antistius offered Antistia's hand in marriage and Pompey accepted. Pompey also convinced his then friend and consul Carbo to act as his defence lawyer. This ensured Pompey's acquittal, and shows how Pompey had to use political connections in instances where he could not save himself.
The most important connection in launching Pompey's career was his friendship with Sulla. Because Strabo had been successful under Sulla in the social war, Sulla already trusted Pompey. Although young, Pompey was able to recruit a legion from Picenum, Appian says this is because of the influence his father had there. (App.Civil Wars.236). By 83BC Pompey was able to join Sulla at Brundisium, bringing with him three legions . Sulla offered his step-daughter in marriage to cement their political alliance. Pompey quickly divorced Antistia and accepted the marriage. At this point in time, after the death of Cinna, Sulla almost had complete control of Rome, and was therefore in a position to give Pompey much needed experience.
Sulla could give Pompey opportunities, but Pompey alone could make his mark as a general. Pompey was sent to Sicily and Africa to counter Carbo and Perpenna when he was twenty-four. Despite being young, Pompey was tough and managed to deal with the situation quickly. However there is little evidence to suggest that he did this using particular cunning or skill; it seems simply because he...