Analysing the tradiiton
Umar’s curious role as a debt-ridden beggar on his deathbed
Sahih al-Bukhari provides a detailed account of Umar's final days including his instructions, one being as follows:
يَا عَبْدَ اللَّهِ بْنَ عُمَرَ، انْظُرْ مَا عَلَيَّ مِنَ الدَّيْنِ، فَحَسَبُوهُ فَوَجَدُوهُ سِتَّةً وَثَمَانِينَ أَلْفًا أَوْ نَحْوَهُ، قَالَ: إِنْ وَفَى لَهُ، مَالُ آلِ عُمَرَ فَأَدِّهِ مِنْ أَمْوَالِهِمْ، وَإِلَّا فَسَلْ فِي بَنِي عَدِيِّ بْنِ كَعْبٍ، فَإِنْ لَمْ تَفِ أَمْوَالُهُمْ فَسَلْ فِي قُرَيْشٍ، وَلاَ تَعْدُهُمْ إِلَى غَيْرِهِمْ، فَأَدِّ عَنِّي هَذَا المَالَ
…`Umar further said, "O `Abdullah bin `Umar! See how much I am in debt to others." When the debt was checked, it amounted to approximately eighty-six thousand. `Umar said, "If the property of `Umar's family covers the debt, then pay the debt thereof; otherwise request it from Bani `Adi bin Ka`b, and if that too is not sufficient, ask for it from Quraish tribe, and do not ask for it from any one else, and pay this debt on my behalf."
(Source: Sahih al-Bukhari 3700In-book reference : Book 62, Hadith 50USC-MSA web (English) reference : Vol. 5, Book 57, Hadith 50)
Observation
So we learn two things from this narration:
1) Umar has incurred debts amounting to eighty-six thousand dirhams
2) He instructed that the debt be paid off from the property of `Umar's family, Bani `Adi bin Ka`b or the Quraish tribe,
We find it curious that Umar was looking to others to pay off his debts when his own personal assets could be sold off to cover his debts? This can be evidence from a narration on Sahih al-Bukhari, “the Book of Wills” on the authority of Ibn Umar:
حَدَّثَنَا قُتَيْبَةُ بْنُ سَعِيدٍ، حَدَّثَنَا حَمَّادٌ، عَنْ أَيُّوبَ، عَنْ نَافِعٍ، عَنِ ابْنِ عُمَرَ ـ رضى الله عنهما ـ أَنَّ عُمَرَ، اشْتَرَطَ فِي وَقْفِهِ أَنْ يَأْكُلَ مَنْ وَلِيَهُ وَيُوكِلَ صَدِيقَهُ غَيْرَ مُتَمَوِّلٍ مَالاً.
When `Umar founded an endowment he stipulated that its administrator could eat from it and also feed his friend on the condition that he would not store anything for himself from it.
(Source : Sahih al-Bukhari 2777In-book reference : Book 55, Hadith 40USC-MSA web (English) reference : Vol. 4, Book 51, Hadith 38 (deprecated numbering scheme)
The personal wealth of Umar was considerable as his fortunate heirs found.
Ibn Hajar al-'Asqalani recorded:
Umar ibn Shabbah has narrated in Tarikh Al-Madina with an authentic chain from Nafi who said: "How can Umar be in debt while indeed a single man from among his heirs sold his inheritance for a hundred thousand?!"
(Source: Fatḥ al-Bārī fī Sharḥ Ṣaḥīḥ al-Bukhārī, commentary on Hadith number 3700)
Comment
When someone is on his deathbed, his first priority will be to appoint an administrator who will be responsible for selling of his assets to ensure that whatever debts are outstanding are paid off from his estate. Heirs or loved ones of the person have to take on the responsibility of using the deceased person’s wealth to pay off their debts. Why was Umar therefore looking to others to pay off his debts rather than have his contribute to cover his liabilities, rather than insist his own assets be utilised to meet his debts? One is all the more puzzled considering the fact he amassed considerable wealth he accumulated, after all just one his heirs his father's share for a hundred thousand dirhams. Why then was Umar pleading poverty and insisting that others paid off his debts?