The Messenger of Allah ﷺ said, "O Allah, strengthen Islam through whichever of these two men is more beloved to You, Abu Jahl or Umar bin Khattab." The more beloved of the two to Him was Umar bin Khattab.
أن رسول الله ﷺ قال: اللهم أعز الإسلام بأحب هذين الرجلين إليك بأبي جهل أو بعمر بن الخطاب. فكان أحبهما إليه عمر بن الخطاب.
Tirmidhi (3681) and Ahmad (5696) narrated it, and Ibn Hibban (6881) graded it sahih, all of them through the route of Kharija bin Abdullah Ansari, from Nafi, from Ibn Umar, who related it.Tirmidhi said, "This is a hasan sahih hadith, rare, from the hadith of Ibn Umar," and that is indeed so, for Kharija bin Abdullah Ansari is disputed, though he has been corroborated.Hakim narrated it (3/83) through the route of Shababa bin Sawwar, who said, Mubarak bin Fadala narrated to us, from Ubaydullah bin Umar, from Nafi, from Ibn Umar, that the Prophet ﷺ said, "O Allah, support the religion through Umar bin Khattab."As for his saying, "O Allah, strengthen Islam through whichever of these two men is more beloved to You," this was at the beginning of the matter. That is, the Prophet ﷺ first prayed for the two of them together, then later prayed for Umar bin Khattab alone, because he was the more beloved of the two to him.