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Firstly:
Imam Ahmad (17405), at-Tirmidhi (3686) and al-Haakim (4495) narrated via Mishrah ibn Haa ‘aan, from ‘Uqbah ibn ‘Aamir (may Allah be pleased with him) who said: I heard the Messenger of Allah (blessings and peace of Allah be upon him) say: “If there were to be a Prophet after me, it would be ‘Umar ibn al-Khattaab.” The scholars differed concerning this hadith. It was classed as saheeh by al-Haakim, and adh-Dhahabi agreed with him. It was classed as hasan by at-Tirmidhi and by al-Albaani in Saheeh at-Tirmidhi.
See a list of different narrations of the hadith on the following link [in Arabic]:
http://www.ahlalhdeeth.com/vb/showthread.php?t=270544
Some of the scholars were of the view that the hadith is da‘eef and flawed:
Ibraaheem ibn al-Haarith said that Abu ‘Abdillah – i.e., Imam Ahmad – was asked about the hadith of ‘Uqbah ibn al-Haarith, “If there were to be a Prophet after me, it would be ‘Umar”.
He said: Cross it out, for in my view it is munkar (odd).
End quote from al-Muntakhab min ‘Ilal al-Khallaal (p. 191).
The fault with it is: Mishrah ibn Haa‘aan. Although he was regarded as trustworthy by Ibn Ma‘een, Ibn Hibbaan said: He narrated odd (munkar) reports from ‘Uqbah for which there is no corroborating report, so the right thing to do is ignore those reports of which he was the only narrator.
End quote from Tahdheeb at-Tahdheeb (10/155).
This is one of the reports of which he was the only narrator from ‘Uqbah, so it is munkar (odd) according to the view of Ibn Hibbaan. This is a matter in which he is in agreement with the view of Imam Ahmad. But there is corroborating evidence for it in the hadith of ‘Ismah, which was narrated by at-Tabaraani in al-Kabeer (475). Its isnaad includes al-Fadl ibn al-Mukhtaar. Abu Haatim said: His hadiths are munkar (odd); he narrated false reports.
Al-Azdi said: His hadith are very odd (munkar)
Ibn ‘Adiyy said: His hadiths are munkar; most of them have no corroborating report.
Meezaan al-I‘tidaal (3/358).
There is another corroborating report in the hadith of Abu Sa‘eed. Al-Haythami said:
it was narrated by at-Tabaraani in al-Awsat. Its isnaad includes ‘Abd al-Mun‘im ibn Basheer, who is da‘eef (weak).
End quote from Majma‘ az-Zawaa’id (9/68).
‘Abd al-Mun‘im ibn Basheer is matrook muttaham (i.e., his hadith is to be rejected and he is accused of lying). Ibn Hibbaan said: His hadith is very odd (munkar), and it is not permissible to quote him as evidence.
Al-Khitli said: I heard Ibn Ma‘een say: I came to ‘Abd al-Mun‘im and he showed me the reports of Abu Mawdood, approximately two hundred fabricated hadiths.
End quote from Meezaan al-I‘tidaal (2/669).
These two corroborating reports cannot be counted because they are extremely weak.
See the comments of the commentators on al-Muntakhab min ‘Ilal al-Khallaal (190-192).
Secondly:
If we assume that the hadith is saheeh, we may ask:
Why did he say “If there were to be a Prophet after me, it would be ‘Umar” and not that it would be Abu Bakr, when Abu Bakr (may Allah be pleased with him) was better than ‘Umar according to the consensus of Ahl as-Sunnah?
The scholars had several views concerning that, including the following:
· That this comes under the heading of knowledge of the unseen which no one knows except Allah, and such matters are not to be worked out on analogy or rational estimates. If it were the case that there would be another prophet after the Prophet (blessings and peace of Allah be upon him), it would be ‘Umar, and in that case Allah would facilitate the means and causes of that, and He would make ‘Umar (may Allah be pleased with him) qualified for that, and would perfect his character so that he would be fit to have the status of Prophethood.
·To demonstrate that Prophethood is not by entitlement or because of something in a person that makes him deserving of Prophethood; rather it is purely by the choice and selection of Allah, may He be exalted.
Abu Bakr al-Kalaabaadhi (may Allah have mercy on him) said:
The Prophet (blessings and peace of Allah be upon him) was speaking of something that did not happen, and describing how, if it were to happen, it would happen. This is like when Allah, may He be exalted, spoke of things that did not happen and how, if they were to happen, they would happen, in the verses in which He says (interpretation of the meaning):
“But if they were returned (to the world), they would certainly revert to that which they were forbidden. And indeed they are liars”
[al-An‘aam 6:28]
“Our Lord! Bring us out of this; if ever we return (to evil), then indeed we shall be Zalimoon: (polytheists, oppressors, unjust, and wrong-doers, etc.)”
[al-Mu’minoon 23:107].
Similarly, the Prophet (blessings and peace of Allah be upon him) said: “If there were to be a Prophet after me, it would be ‘Umar”, which highlights the virtue that Allah created in ‘Umar (may Allah be pleased with him) and the characteristics or virtues that exist in the Prophets and Messengers.
Thus he stated that ‘Umar possessed some of the characteristics of the Prophets and some of the virtues that are found in the Messengers, that made his state close to that of the Prophets (blessings and peace of Allah be upon them all).
And it may be that there is another meaning, which is to indicate the fact that Prophethood is not based on entitlement or any quality that a person may have which makes him deserving of Prophethood. Rather it is by the choice and selection of Allah, may He be exalted. Allah, may He be exalted, says (interpretation of the meaning):
“but Allah chooses (for His Messages) such of His Messengers as He will”
[Aal ‘Imraan 3:179]
“Allah chooses Messengers from angels and from men”
[al-Hajj 22:75]
“And they say: ‘Why is not this Qur’an sent down to some great man of the two towns (Makkah and at-Taa’if)?’
Is it they who would portion out the Mercy of your Lord?”
[az-Zukhruf 43:32].
It is as if the Prophet (blessings and peace of Allah be upon him) was referring by implication to some of the characteristics of the Messengers and Prophets (peace be upon them), and that ‘Umar (may Allah be pleased with him) possessed many of those characteristics; if characteristics were to make a man entitled to be a messenger, then ‘Umar would have been a messenger after him.
What proves that is the fact that the main characteristics that ‘Umar possessed, to the exclusion of other people, was his strong commitment to and support for the religion of Islam, his physical strength, his striving to support the religion of Allah and his turning away from worldly matters, and the fact that he was a cause of the truth and Islam prevailing and becoming victorious, and he was the criterion by means of which truth was distinguished from falsehood, for which reason he was called al-Faarooq (the one who distinguishes between truth and falsehood).
The characteristics that people recognise as characteristics of the Prophets are: Sincerity towards Allah, trust in Allah, and turning away from everything except Allah. And that may be manifested in honesty of speech, courage, and generosity. This is what the hadith means, which indicates that these characteristics are among the main characteristics that people see in the Prophets, and the true nature of the relationship between them and Allah is known to no one but Him, may He be glorified and exalted.
Moreover, most of these characteristics were present in Abu Bakr to a greater degree than they were in ‘Umar (may Allah be pleased with them both), yet the Prophet (blessings and peace of Allah be upon him) did not say that if there were to be a Prophet after him it would be Abu Bakr; rather he said that concerning ‘Umar, in order to highlight that Prophethood is based on the will of Allah and on His selection, and it cannot be attained by personal effort.
The words “If there were to be a Prophet after me, it would be ‘Umar” do not indicate that ‘Umar is better than anyone else, because he was not a Prophet, but if he were a Prophet, he would have been better than anyone who was not a Prophet. But as he was not a Prophet, it is possible that someone else was better than him, and that was Abu Bakr (may Allah be pleased with him). And Allah knows best.
End quote from Bahr al-Fawaa’id (p. 238)
· ‘Umar is singled out for mention because in many instances during the Prophet’s time, he expressed his view and Qur’an was revealed that supported his view, so his view was in accordance with what was revealed of Qur’an later on. Thus he was as close to Prophethood as he was to the Qur’an, but there is no Prophet after Muhammad (blessings and peace of Allah be upon him).
Al-Minnaawi (may Allah have mercy on him) said:
Ibn Hajar said: ‘Umar is singled out for mention because of the many incidents during the Prophet’s time when he expressed his view, concerning which Qur’an was subsequently revealed that agreed with his views.
End quote from Fayd al-Qadeer (5/325).
This is like what the Prophet (blessings and peace of Allah be upon him) said to ‘Ali (may Allah be pleased with him): “You are to me like Haroon to Moosa, except that there is no Prophet after me.”
Narrated by al-Bukhaari (4416), Muslim (2404).
‘Ali was close to the Prophet (blessings and peace of Allah be upon him) because of his close ties of kinship with him, in addition to what he heard of strong faith. And the same is true here.
Hence the scholars only mention this hadith in the context of discussing the virtues of ‘Umar; none of them mention it to prove that ‘Umar is better than Abu Bakr, because they are unanimously agreed that Abu Bakr is the best of this ummah after its Prophet (blessings and peace of Allah be upon him).
Shaykh al-Islam Ibn Taymiyah (may Allah have mercy on him) said, after quoting the hadith mentioned above and a number of other hadiths that speak of the status of ‘Umar and that he is inspired (muhaddath):
Despite that, as-Siddeeq [Abu Bakr] attained a higher level of perfection and attained a perfect level of believing the Prophet, so he did not acquire any knowledge except through the Prophet, and the Prophet is infallible, whereas the one who is inspired (muhaddath), like ‘Umar, sometimes follows his heart and what he is inspired with, but his heart is not infallible. Therefore he has to check whatever he is inspired with against what the Messenger brought; then if it is in harmony with that, he should accept it, but if it is contrary to that, he must reject it.
Hence ‘Umar retracted some of his suggestions, and the Sahaabah would sometimes debate with him and quote evidence to him to prove that his view was not correct; when proof from the Qur’an and Sunnah became clear to him, he would go back to that and abandon his view.
Abu Bakr as-Siddeeq, on the other hand, only took knowledge from the Messenger, not from the inspiration of his heart. Therefore he was more perfect than the one who was inspired (muhaddath – i.e., ‘Umar). After Abu Bakr, there was no siddeeq (person strong and true in faith) who was better than him, and after ‘Umar there was no muhaddath (person who is inspired) who was better than him.
End quote from ar-Radd ‘ala al-Mantiqiyyeen (514).
For more information, please see the answer to question no. 7186.
And Allah knows best.