I asked Ayesha, "Which of the Messenger of Allah's ﷺ companions was most beloved to him?"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 fell silent.
قال 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.
Tirmidhi (3657), Ibn Majah (102), and Abu Yaala (4732) all narrated it through chains going back to Jareeri - who is Saeed bin Iyas - from Abdullah bin Shaqiq, who related it. Jareeri is trustworthy, though he became confused in his later years. However, 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 heard from Jareeri before his confusion set in. Tirmidhi said, "This is a hasan sahih hadith."