This paper deals with the views and claims of the Italian politician and orientalist Leone Caetani in his work Annali Dell'Islām, which deals with the Prophet's preparation of an army to be sent to the Syrian region before his death and his appointment of Usāma b. Zayd as the commander of the military, which took place in the 11th year of the Hijrah in Islamic history. Due to its importance, every Muslim wants to learn the Islamic sciences from their basic sources accurately, especially the life of the Prophet Muhammad. For this purpose, Muslim scholars researched this field and produced many works. Western scholars also conducted research in this field for different purposes and eventually produced works within the scope of Orientalism. Leone Caetani (d. 1935) was one of the orientalists who aimed to study the religion, culture, thought, economic, and social life of the East. He wrote his work Annali Dell'Islām in ten volumes. The translation of the work from Italian by Hüseyin Cahit Yalçın between 1924 and 1927 caused a great outrage in our country. Due to the fact that historians live in different geographies and are nourished by the culture in which they live, they have often failed to do so, even though they want to approach events objectively. Therefore, it is important to approach orientalist writers' works carefully and evaluate their content. In addition, when differences in beliefs are added to the aforementioned factors, the picture that emerges can be far from scientific. As a matter of fact, this situation is also observed in Leone Caetani. Caetani's work contains many subjective, negative thoughts and incomplete and erroneous information. Although it is the product of many years and labor, it is seen that the work moves away from objectivity and scientificity at some points. Babanzâde Ahmet Naim, and Yusuf Ziya Yörükân wrote articles against his subjective and negative views which do not reflect the truth, and Âsım Köksal wrote a refutation to the first volume. However, when we searched the literature, we realized that previous studies did not include this subject, and the need for research arose. In this study, the information given by Caetani under the title "Preparations for Usāma's departure to Balqa" is subjected to analysis, criticism and evaluation. The aforementioned subject is discussed within orientalist Leone Caetani's views and claims. For this purpose, the main sources such as al-Wāqidī's al-Mag̲hāzī, Ibn Hishām's al-Sīra al-nabawiyya, al-Ṭabarī's Tarikh al-Umam wa al-Muluk, and many others such as the works of Ibn Saʿd, al-Yaʿqūbī, al-Masʿūdī, Yāqūt al-Ḥamawī, al-hahabī, Ibn Kathīr, etc., and the al-Kutub al-sitta in the field of hadīth have been examined to obtain information on the subject. In the light of the information obtained, Caetani's views and claims were objectively evaluated. As a result of our evaluations, we have found both accurate information and erroneous points. For example, while quoting information from al-Masʿūdī, he expressed Usāma's campaigns in the 10th and 11th years of Hijrī as if they took place in the same time without specifying the difference in years. This and similar errors have been explained with the information we have obtained from the main sources.