After the defeat of Antiochus III in the Battle of Magnesia in 190 BC, Seleucids had to withdraw behind the Taurus Mountains to the East. This event caused a social decline and economic recession in many sites in Rough Cilicia. During the period between the second century BC and Pompey's campaign, a decline of Seleucid power in the region occurs. Romans' struggle with Mithradates VI who had supported the pirates in the Eastern Mediterranean is another reason of the chaotic circumstances in the region. Many sites abandoned, legal trade activities slowed down, production of the goods almost ceased and people had to incline the piracy because of poverty. It has always been a question where and under which conditions pirates were living, hiding and what their relations were as well as their impact on the regions they were associated with. This study aims to focus on these issues in the light of recent archaeological discoveries from the excavations of Olba in Eastern Rough Cilicia. The finds that will enable us to get information concerning the period (first century BC) mainly consist of coins as well as DSA pottery sherds and a couple of fragments belonging to glass bowls that were typical for the time. A significant numismatic find is a Kolophon coin that can enlight the presence of pirates in Olba. The total number of coins belonging to the first century BC from Olba is 32. These are coins of Elaiussa, Korykos, Seleucia ad Calycadnum, Soli and Tarsus. For the similar coin types that were previously published, a large period of time in between the second and first century BC were usually given. In order to make a more accurate dating, the coins of Elaiussa provide concrete evidence. The latest use of ethnicon E Lambda AIOY Sigma I Omega N, dates to the year 12 BC for the coins of Elaiussa. After that date, the coins of Elaiussa bear the name "Elaiussa Sebaste". On the other hand, Pompey's victory over the pirates and Mithradates VI in 67 BC can be regarded earliest date of issue for Elaiussa coins. Before that date, in the early first century BC it does not seem possible to any site in the region to struck coins under the chaotic conditions. Our study aims to evaluate the circumstances in Olba through archaeological and numismatic material in that very significant period of time.