Khalifa Abu Bakr - Things which he did not do, and wished that he should have done them

The first thing which he did not do, but wished that he should have done it was that when Asha'as bin Qais was brought to him as a captive he should have ordered him to be killed, and should not have pardoned him. The second thing was that when he sent the forces against the apostates he should have remained at Zul Qissa, so that he could have proceeded to the help of the Muslim force fighting against the apostates. The third thing was that when he commissioned Khalid to proceed to the Syrian front, he should have sent Umar to Iraq and in this way he should have spread both his hands in the way of Allah. Asha'as the Kinda chief was deceitful by nature, and Abu Bakr not only pardoned him, but married his sister to him. Abu Bakr felt that that was a mistake as Asha'as was a faithless person. Abu Bakr directed the apostasy campaign from Madina. Abu Bakr felt that a better base for such operations was Zul Qissa.

When Khalid was withdrawn from the Iraq front, the Muslim position on this front became weak. It would have been a better course of action if reinforcement should have been sent to Iraq under the command of a leader like Umar.

Things that he should have inquired from the Holy Prophet. The first thing which Abu Bakr wished to have inquired from the Holy Prophet was as to who should be his successor. The second thing was what share should be allowed to the Ansar in the administration. The third thing was as to what part of the inheritance should be allowed to a niece or a paternal aunt. The caliphate issue has remained a source of great headache to the Muslims and Abu Bakr felt that if there had been any definite instructions of the Holy Prophet on the point that could have eased the situation. The question of the equation between the Ansars and the emigrants also involved considerable controversy, and it would have been in the fitness of things if some definite guidance from the Holy Prophet on the point was forthcoming. The question of giving share to a niece or a paternal aunt involved difficulty and if there had been a specific ruling from the Holy Prophet that would have solved the point.