The Closest Confidants with Shaykh Abdullah Waheed | Session 3
By Shaykh Abdullah Waheed, Shaykh Mohamed Almasmari, Mufti Abdul Wahab Waheed | 2026-07-30T16:41:11.258101+00:00 | Topic: Khutbah
The Closest Confidants — Session 3: Umar ibn al-Khattab
Assalamu Alaikum Warahmatullahi Wabarakatuh. Welcome everyone. Alhamdulillah, alhamdulillah. We are so blessed. I hope everyone is enjoying Ramadan.
Resources and Books Used for This Series
So what book am I using for these lessons? There are a few books. One is the book Tarikh al-Khulafa of Imam Suyuti — it is a history on the Khulafa Rashidun, including the fifth, Umar bin Abdul Aziz. That was one book I use; I did mention that.
There is also Ali As-Salabi — he is, if I am not wrong, a Libyan author who is recent; he is alive, mashaAllah. He writes really well. He writes his books in Arabic and then they are translated into English. That is the second author I would look into. These are the two main books, and then I go into the Hadith where these Sahaba are mentioned — like Umar and Abu Bakr — and try to dissect from the Ummul-Kutub, the encyclopedia versions of the books, and have the narrations of them. And then there are things called Manakib — the virtues of certain Sahaba — so I look into the Manakib from different scholars and different authors.
But these two books for a beginner reader would be sufficient, especially Ali As-Salabi's book. And because I do a lot of Tafsir preparation, I also come across a lot of readings that talk about Umar or Abu Bakr and I kind of remember where I read them, go back into them, and pick them out. So that is how I try to copy-paste some of the information the elders and our senior scholars have put together. I am just a person that transfers what I have read or heard.
Today's Topic: Umar ibn al-Khattab
These are the two people I spoke about — I want to speak about because I really look up to these two Sahaba extremely immensely. We are going to have a very interesting class today. We are going to go over the virtues of this Sahabi, some of his highlights of him accepting Islam, and then next hour, the next class — it is unfortunate we only have two hours — I want to focus on some of the elements of this Sahabi's justice: just from that component of how fair he was, how just he was.
Does anyone know who I am speaking about today? Umar ibn al-Khattab, radiyallahu anhu.
Bismillah al-Rahman al-Rahim, alhamdulillahi Rabbil 'alamin wa salatu wa salamu 'ala sayyidina khatam al-nabiyyina wa 'ala alihi wa sahbihi ajma'in wa ba'd.
Brothers and sisters, I have been speaking for the past six hours, webinar after webinar, alhamdulillah. So if you cannot hear me and my voice becomes timid, just remind me. I can speak a little louder, but I am not going to be speaking very loud because after this I have more going on. We are not done yet.
Brothers and sisters, I cannot thank you enough for joining. You know, we as instructors of the Sunnah of the Prophet ﷺ — we are going over this together. If you were not in this class together with me, I would not be able to attain the reward that I am attaining just by sitting with you and sharing this and remembering these righteous people. And when we talk about such people, we are impressed by them and then we want to be like them.
Today the world is impressed by these unimpressive people. They do some silly things — and you would be amazed at the biggest subscriptions on YouTube: people who are pranksters, people who do jokes, who lie and hurt people, and video gamers. People follow these people because that is how they find their amusement. It is important that we learn. I wish there was someone that could express the life of Umar ibn al-Khattab correctly.
Who Was Umar ibn al-Khattab?
Umar ibn al-Khattab is a very interesting person. He was 13 years younger than the Prophet ﷺ — he was born 13 years after the Year of the Elephant, which was the year the Prophet ﷺ was born. People say that 40 men had accepted Islam prior to Umar ibn al-Khattab, and 11 women had accepted Islam before him. So in one version it says 54 men had accepted Islam and 11 women had accepted Islam — so we are talking about he is in the 60s in terms of the numbers. He accepted Islam much later, after the earlier Sahaba accepted Islam.
I also want you to remember the age of Umar ibn al-Khattab — he is 13 years younger than the Prophet ﷺ. He is a son of Khattab, and he is considered to be the father of Hafsa. That is his real title: Abu Hafs. There is nothing wrong with the father or mother being called by their daughter's name — usually it is always the name of their eldest son — but Umar, who is the most masculine figure that you can remember, is recognized by his daughter. SubhanAllah.
The first narration in Sahih Bukhari, the first narration in Sahih Muslim, the first narration in the famous work of Riyad as-Salihin — the most famous narration — what is it? It is a narration narrated by Umar ibn al-Khattab, and it is about intention. It is the narration of:
"All deeds are by their intentions." (Sahih al-Bukhari, Hadith 1; Sahih Muslim, Hadith 1907)
It is so important, so amazing — the way the narrator narrates this narration. It says: from the leader of the believers, Abi Hafs, the father of Hafsa, Umar ibn al-Khattab, radiyallahu anh. Amazing. So that is something I wanted to share and remind you all of.
Can I ask — what is Umar's nickname? He has a few names, but one famous name that the Prophet ﷺ gave him. While you guys think about the name, I will tell you how many narrations Umar ibn al-Khattab narrated. He narrated 539 hadith — 539 narrations. Not that much. Even Abu Bakr as-Siddiq, not many — 400–500. These are the elders of the Sahaba; they do not narrate too much.
This is one of the accusations of the Orientalists — that the senior Sahaba do not narrate as much as the junior Sahaba like Abdullah ibn Abbas, Jabir, Abdullah ibn Umar, and Anas, radiyallahu anhum. The answer to that is: the senior Sahaba, number one, had passed away when hadith transmission started. Before, when the senior Sahaba were alive, the focus was on the Quran and the preservation of the Quran. Abu Bakr, Umar, and Uthman — Uthman was considered to be the publisher; he had it written out to the other governments. So that is one major answer.
And then hadith and the science of hadith picked up momentum and steam after the time of Uthman ibn Affan, which makes sense. So there are some people who are skeptics, and one of the arguments is that the young Sahaba narrate more than the elders. The elders, number one, passed away earlier, and number two, they were focused more on the preservation of the Quran. The transmission of hadith came when the Sahaba started passing away — now their students and their students' students need to know their religion. So they would start transmitting narrations.
Yes — Al-Farooq is his famous nickname and title that the Prophet ﷺ gave him. I will tell you when he got that title today.
The Virtues of Umar ibn al-Khattab
The Prophet ﷺ had a special eye on Umar ibn al-Khattab. Before we go to his Islam and his life before Islam, I want to tell you a few things about his virtues. He accepts Islam and there are so many virtues, but I want to mention some of the virtues that the Prophet ﷺ said about Umar ibn al-Khattab that were very remarkable and that kind of summarize who this great human being was.
Umar and the Women Around the Prophet ﷺ
One of the most beautiful narrations of Umar ibn al-Khattab's accolades and virtue is this: once the Prophet ﷺ was sitting with his wives and some women from outside his family who were asking the Prophet ﷺ some questions. They were very respectful, but they were excited to be in the Prophet's gathering and they wanted to ask him questions — so some were louder than others. Umar ibn al-Khattab walks in, and the women — يَبْتَدِرْنَ الْحِجَابَ — they take extra sheets of covering and put them upon themselves. They covered themselves further and became very quiet, very timid, very soft in their discussion, because it was Umar ibn al-Khattab who had come in.
The Prophet ﷺ was smiling. The Prophet ﷺ said to him — and the women asked: أَضْحَكَ اللَّهُ سِنَّكَ يَا رَسُولَ اللهِ — "May Allah keep you smiling, O Messenger of Allah, why are you smiling?" He said: before you came in, they were all loud, very excited, asking me questions, and when you came in, right away they became silent and quiet.
So Umar turned to them and said: يَا عَدُوَّاتِ أَنْفُسِهِنَّ — "O enemies of yourselves!" — أَتَهِبْنَنِي وَلَا تَهِبْنَ رَسُولَ اللهِ ﷺ — "Why are you intimidated by me when the Prophet is here? Why are you not showing more respect to him?" So Umar felt that the women were more intimidated by him — so the women made a very clear disclaimer. They said:
وَأَنْتَ أَغْلَظُ وَأَفَظُّ مِنْ رَسُولِ اللهِ — "We are quiet because we are scared of you, because you are far more rough and tough than the Prophet ﷺ. The Prophet ﷺ is soft and accommodating compared to you who is so abrupt and rough sometimes."
So Umar was literally roasted by the women. I have stories of women roasting Umar — those stories are my favorite. When the women of Medina kind of take a toll on the Amir of Medina, this great giant — what I also enjoy is the response of Umar al-Khattab. It is unbelievable how he would just be so gentle, so smart, so wise.
The Shaytan Fears Umar
The Prophet ﷺ, knowing Umar was hurt after being told off by the women, said one of the most praiseworthy things about him:
"O son of al-Khattab! By the One in Whose Hand is my soul, the shaytan never meets you taking a path except that he takes a path other than yours." (Sahih al-Bukhari, Hadith 3683; Sahih Muslim, Hadith 2396)
O Umar, if you were to walk one way, the shaytan would never walk the same way. You are so strong in your faith that the shaytan has no game on you. You know, the shaytan said to Allah that he would come in front, come from behind, from the right, from the left —
From every direction — but the shaytan will never walk the direction of Umar ibn al-Khattab. When Umar is around, the devil is away.
Truth Upon the Tongue of Umar
The Prophet ﷺ said:
"Verily Allah has placed the truth upon the tongue of Umar and his heart." (Sunan al-Tirmidhi, Hadith 3682; classified as hasan)
There are more than 17 to 21 places in the Quran where Umar said something in the presence of the Prophet ﷺ, the Prophet ﷺ may have shared a different opinion, and Allah agreed with Umar ibn al-Khattab's opinion. That is amazing. Umar would speak as if the truth was descending on his tongue, and then Allah would send an ayah to support his opinion. That was Umar ibn al-Khattab in many ways.
Jibreel Sends Salam to Umar
Once Jibreel came from the skies — this is narrated by al-Tabarani — and said: give Umar my salam, and I have something to tell him: that when he gets angry, his anger gives Islam honor. His anger is not negative but something positive. And the second thing: his pleasure — when he agrees to something — that is a decision of Allah. That is what Allah likes.
The Angels Admire Umar
The Prophet ﷺ said: there is not an angel in the heavens except that it admires Umar ibn al-Khattab, and there is not a devil on this earth except that the jinn or devil is afraid of Umar ibn al-Khattab. This is how Umar ibn al-Khattab was. I just feel like people need to understand and appreciate who this great man was.
The Dream of the Palace in Jannah
The Prophet ﷺ told Umar ibn al-Khattab and the Sahaba two dreams — and these are the two dreams narrated by Bukhari and Muslim that I want to share with you.
The Prophet ﷺ says: I was in my dream — I was in Jannah — I saw a woman doing wudhu next to a palace. I asked and was told this was the palace of Umar ibn al-Khattab. That is when the Prophet ﷺ said: "O Umar, I remembered your self-respect and your dignity and your possessiveness over your home — I stepped back. I did not want to trespass." So the Prophet ﷺ saw the palace of Umar ibn al-Khattab in Jannah.
The Dream of the Milk
The second dream is also very interesting. The Prophet ﷺ says: I was sleeping; in my dream I saw that I was drinking milk. I was drinking so much — I could feel the coolness of the milk coming out of my nails, meaning I felt the coolness in my hands. Then I gave the rest of the milk that was in the bowl to Umar ibn al-Khattab.
So Umar ibn al-Khattab asked: "What does that mean — that you drank from this bowl and then you gave it to me?" The Prophet ﷺ said: it means knowledge. My knowledge — I will transfer to Umar ibn al-Khattab. The remaining of the Prophet's knowledge will be given to Umar ibn al-Khattab. That is very powerful.
So Umar ibn al-Khattab came to be a very knowledgeable person. People do not realize how knowledgeable he was. There were times when the greatest Mufassirs of the Prophet's time and the Sahaba's time did not know the interpretations of certain narrations and verses — they would ask Umar ibn al-Khattab.
Umar Wins the Gold Medal of Arafah
On the Day of Arafah — anyone who has been to Arafah will realize it is a very special place — everyone was worshipping Allah. Imagine Arafah with the Prophet ﷺ and Abu Bakr, Umar, Uthman, Ali, and the great Sahaba, all in ibadah, all worshipping Allah. The Prophet ﷺ was told by Jibreel:
(Narrated in al-Mu'jam al-Kabir of al-Tabarani)
Allah was boasting about all the Sahaba worshipping on the Day of Arafah, the 9th of Dhul Hijjah — "Look at my Sahaba, look at this person, look at that person, look at all these Sahaba who are worshipping." But then Allah singled out one person — one person who won Allah's attention like the gold medal of Arafah that day. And that was Umar ibn al-Khattab. Imagine — the best day of the year, in the company of the best people, and the winner comes out to be Umar ibn al-Khattab. That is a narration I very much cherish.
Loving Umar Means Loving the Prophet ﷺ
There is a narration that the Prophet ﷺ said:
"Whoever hates Umar hates me, and whoever loves Umar loves me."
Anyone that makes Umar angry gets me angry, and anyone that loves Umar ibn al-Khattab loves me.
Umar the Muhaddath
Then the Prophet ﷺ said:
"Allah never sends a prophet except that there is among his followers a muhaddath, and the muhaddath of my ummah is Umar ibn al-Khattab." (Sahih al-Bukhari, Hadith 3689; Sahih Muslim, Hadith 2398)
Muhaddath are those who speak as if revelation is descending to them — they speak under inspiration, so pure, so accurate, so correct. And that was Umar ibn al-Khattab.
The Immensity of Umar's Knowledge
Ibn Mas'ud, radiyallahu anh, says: listen to this —
"If the knowledge of Umar were placed on one scale, and the knowledge of all the people of the earth on the other scale, the knowledge of Umar would outweigh theirs."
If the knowledge of Umar ibn al-Khattab was placed on one scale and the knowledge of the entire world on the opposite scale, Umar's knowledge was far greater than the knowledge of the entire world. He was so knowledgeable. And they said: the day he passed away, nine-tenths of knowledge disappeared. That is how knowledgeable he was.
So we ask Allah to give us this understanding of Umar ibn al-Khattab and his virtue — how he was.
The Prophet's Du'a for Umar's Acceptance of Islam
The Prophet ﷺ made du'a — he literally prayed for Umar ibn al-Khattab to become Muslim. This is where I want to talk about how the Prophet ﷺ prayed for Umar ibn al-Khattab to become Muslim, and I will answer that question about Al-Farooq right now.
The Prophet ﷺ used to make this du'a:
"O Allah! Please give Islam honor by one of these two people becoming Muslim — either Umar ibn al-Khattab or Abu Jahl." (Sunan al-Tirmidhi, Hadith 3681; classified as hasan sahih)
These were two influential people of Mecca and they were both against the Prophet ﷺ. I have to say this: when the Prophet ﷺ and the Sahaba were in Mecca, they were tortured by Umar. Umar had a slave by the name Zanira, and Umar would torture her. He was abusive to her. He hated Islam and was against it completely. So the Prophet ﷺ would constantly make this du'a for Umar ibn al-Khattab: "O Allah, please give my dawa to Umar. One day if he becomes Muslim, Allah will give Islam support through him."
The Prophet ﷺ would always work with the public at large, but he also went after some special people who he knew were going to be influential — and if they accepted Islam, they would influence other people. And this was his du'a all the time.
Signs of a Soft Spot: Ja'far's Family and Umar
Ibn Abbas says himself: "I asked Umar ibn al-Khattab, what was the first time you were inspired by the truth?" And Umar ibn al-Khattab talks about this narration himself — how he was inspired to accept Islam.
But one of the most interesting things I have read about Umar's opposition to Islam was the statement of Ja'far. Ja'far's wife, Asma bint Umais — her name was Asma bint Umais, also known as Umm Abdullah — was getting ready to migrate to Abyssinia. They were packing up their luggage. In our culture it would be like a U-Haul truck outside and they were moving from Mecca to Ethiopia.
Umar ibn al-Khattab saw the camels parked outside and luggage being loaded. He comes inside their home and says: "Where are you going?" These were the neighbors of Umar ibn al-Khattab. This is Ja'far — the older brother of Ali, the cousin of the Prophet ﷺ — a very close, very dear member of Mecca. The father of Ja'far is Abu Talib, one of the leaders of Mecca.
So the wife says to Umar: we are leaving to Ethiopia, to the Najashi, because we cannot worship Allah — we are tortured, we cannot do our basic rituals without being tortured — and we are going to a land that is more peaceful and their king is fair.
So Umar ibn al-Khattab became very soft. He was kind of disappointed that they had caused so much trouble to their own relatives and neighbors — people they were so close to — that they were having to move out. He leaves. Ja'far comes, and Ja'far's wife says to her husband Abdullah: "If you were to see Umar ibn al-Khattab right now — that he was sympathetic to our situation — you would assume that one day he would accept Islam. You would think that he has a soft spot for Islam."
And I said this before: having a soft spot for the righteous people is sufficient for Allah to guide you. Maybe you are not righteous yourself, but you have a soft spot for good people, generous people, and people who obey Allah — Allah will give you the tawfiq to become righteous. But if you have hatred and animosity towards good people, Allah will never give you the tawfiq to become righteous.
The Levels of Engagement with Knowledge
The Prophet ﷺ said from this narration you can understand: become a scholar, or become a student of a scholar, or if you cannot become a scholar, at least become a listener. SubhanAllah — all you guys are students of knowledge and you are also listeners of knowledge. I consider myself amongst them also. I do not consider myself a scholar — I consider myself someone who is really intrigued by knowledge.
And if you are not a scholar, if you cannot become a scholar, become a student. Become someone who listens to the knowledge and the discourses of scholars. And if you cannot become a consistent listener — if you cannot tune in to Ramadan Immersion every single day — then tune in to a nightly reflection or something for a few minutes. Do not overwhelm yourself. But if you cannot even do that much, then at the very least: oh muhibban — just love the work that is being done by these scholars. Love the khair. Islam is being spread, things are being taught, people are benefiting — you should feel good about it. You should pray for it and help it.
I was telling my brother the other day — there were some institutions doing some fundraising campaigns online and I told them: all you guys should go online and donate to them, because these are all institutions that are helping Allah's deen and they are serving God. We are passionate about our institute, but we should be equally passionate about others, because they can probably reach people that we cannot reach. So help them out also.
But never become the fifth type — that is dangerous: that you hate knowledge and you hate the people of deen and you look at them in a demeaning way. Unfortunately, post-colonialism there has been this mindset, and some of it has also been the lack of wisdom within the scholars of certain countries. And secondly, there has been a colonial mindset that has been manipulated into the Muslim communities against righteous people or people who are serving God. That has brought a complex against scholars and all righteous people. But again, it is two-sided — the people who are scholars also have to be wise and accommodating, and the people following these scholars have to understand that they are human; they are not perfect.
How Far Umar Seemed from Islam: Ja'far's Warning
When Ja'far's wife said this — that Umar looked sympathetic — Ja'far said something so important that I want us to understand how far Umar was from accepting Islam. This is Ja'far saying:
He said: "The chance of the donkey that is outside the house of Umar's father becoming Muslim is far more acceptable and possible than Umar accepting Islam." Umar accepting Islam was considered far-fetched — not even possible. That is how extreme Umar's opposition to Islam was and how he tried to challenge the Prophet ﷺ.
So the Prophet ﷺ continued to make du'a for Umar ibn al-Khattab, radiyallahu anhu, and he prayed for him.
The Night Umar Heard the Quran
And finally one night — Abdullah ibn Abbas says: one night I went to Mecca to pray at the Haram around the Ka'bah. I got there and I noticed someone praying in the dark. I sat behind. It was the Prophet ﷺ, and he was reading the verses of the Quran — the verses of Surah al-Haqqa.
Surah al-Haqqa is all about the punishments that came to previous nations, then the Day of Judgment, and then Allah speaks about the Quran. In Surah al-Haqqa, Allah says:
So Allah is taking a great, monumental, profound oath by everything that was created — that which we can see and that which we cannot see. "Verily this is the statement of a noble messenger — and it is not the statement of a poet." Because the Arabs would say — they would call the Prophet ﷺ sha'ir majnun — "a crazy poet." And in the 14th Juz there is a very nasty way that people are calling the Prophet ﷺ. The people at that time said: