I asked Ayesha, "Which of the companions of the Messenger of Allah ﷺ was most beloved to the Messenger of Allah?"She replied, "Abu Bakr."I asked, "Then who?"She said, "Umar."I asked, "Then who?"She said, "Then Abu Ubayda bin Jarra."I asked, "Then who?"She remained silent.
قلت لعائشة: أي أصحاب رسول الله ﷺ كان أحب إلى رسول الله؟ قالت: أبو بكر، قلت: ثم من؟ قالت: عمر، قلت: ثم من؟ قالت: ثم أبو عبيدة بن الجراح، قلت: ثم من؟ قال: فسكتت.
Narrated by Tirmidhi (3657), Ibn Majah (102), and Abu Yaala (4732), all of them through routes from Jareeri, who is Saeed bin Iyas, from Abdullah bin Shaqiq, and he mentioned it. Its chain of transmission is sahih, and Jareeri is trustworthy, though he became confused in his later years, but the hadith as narrated by Tirmidhi comes through Ismail bin Ulaya, and as narrated by Abu Yaala comes through Waheeb bin Khalid, and both of them related from Jareeri before his confusion began. Tirmidhi said, "This is a hasan sahih hadith."Among the reports about Abu Ubayda bin Jarra is that Abu Bakr Siddiq said, at the time of the death of the Messenger of ﷺ, at the portico of the sons of Saeda, "I am content for you with one of these two men, Umar or Abu Ubayda." Abu Bakr had put Abu Ubayda in charge of the treasury, meaning the wealth of the Muslims.Among the reports about him is that Abu Bakr Siddiq sent him to Syria as governor, and most of the conquest of Syria was accomplished at his hands. He died in the plague of Amwas in Syria in the year eighteen, at the age of fifty-eight.