All perfect praise be to Allah, The Lord of the worlds. I testify that there is none worthy of worship except Allah and that Muhammad is His slave and Messenger.
Anas ibn Maalik, may Allah be pleased with him, narrated that the Prophet said:
“The most affluent of the people in this world, of those who will go to Hell, will be brought on the Day of Resurrection, and he will be dipped in the Fire once. Then it will be said, 'O son of Aadam (Adam), did you ever see anything good? Did you ever have any pleasure?' He will say, 'No, by Allah, O Lord.' Then the most destitute of the people in this world, of those who will enter Paradise, will be brought and dipped in Paradise once, and it will be said to him, 'O son of Aadam, did you ever see anything bad? Did you ever experience any hardship?' He will say, 'No, by Allah, O Lord. I never saw anything bad, and I never experienced any hardship.'” [Muslim]
As you see, the hadeeth does not state who this man, who is the most miserable one, is, and there is no mention of the type of distress and misery that he was afflicted with in this worldly life. However, this description is sufficient to clarify the greatness of the matters of the Hereafter and what Allah has prepared for the doers of good and what He had promised the bad doers; and also that this worldly life, despite all its pleasures and its misery, is insignificant and that all this comes to an end and has no effect when a person moves to its opposite in the Hereafter. So there is no point in trying to find out who is the most miserable and who is the most afflicted person in this worldly life.
Ibn Hubayrah said in Al-Ifsaah, “This hadeeth is evidence that no matter the amount of bliss of a person from the beginning of his life until the day of his death, though he might have lived the longest life, he is overwhelmed – to the point that he forgets everything that he enjoyed in his life – by just one immersion in Hellfire, and no matter the hardship that a person experienced, despite his long life, he is overwhelmed – to the point that he forgets all the misery that he experienced – by just one immersion in Paradise.”
Allah knows best.