The problem apparently is his third child - and only son - Moin Nawaz D. Kaskar, 31, who has turned his back on the "family business" is a devout Muslim who has chosen to become a Maulana, or a cleric-cum-religious teacher.
"Moin is understood to be deadly against his father's illegal activities which have given the entire family a notorious reputation worldwide and made many of them wanted fugitives everywhere," Thane Anti-Extortion Cell head Pradeep Sharma told IANS.
He said this and other nuggets of an internal strife in the family tumbled out in bits and pieces during the ongoing interrogation of Iqbal Ibrahim Kaskar, Dawood's younger brother, who was nabbed in three extortion cases last September by the Thane AEC.
Iqbal Kaskar has informed the investigators that a deeply worried Dawood is afflicted by bouts of despondency over who would look after and handle his vast underworld empire in the future.
More so, as his other brother Anees Ibrahim Kaskar is now ageing and reportedly not in robust health, other brothers are deceased and no reliable close relatives available to take over the reins of the empire.
"His son is practically estranged from the family and all its businesses since the past few years, but it is not clear if he is on speaking terms with his father," said Sharma, a former "encounter specialist" dreaded by the mafia, with many scalps of dreaded criminals under his belt.
Iqbal Kaskar told the investigators that his nephew Moin is now a respected and qualified Maulana, who is a 'Hafiz-e-Quran', having memorized the entire Holy Quran which comprises 6,236 verses.
Besides, he has discarded the comforts of the family's palatial bungalow in the fashionable Clifton area in the posh Saddar suburb of Karachi and opted to live a mendicant's life in a mosque adjacent to their home.
Moin's main religious activities comprise teaching Holy Quran and Islamic preachings to young children, leading the call of prayers and congregation of 'namaz' at various occasions and other social-religious responsibilities associated with a cleric.
"Its clear that Moin, who could have inherited his father's vast legal and illegal business empires, ironically, has decided to become a man of God and completely shunned a life of luxury which was at his command," Pradeep Sharma said.
Earlier, Moin, who is a business management graduate, used to help out his father in some of his line of works, but gradually drifted away to the "divine call of Allah".
A handsome young man, in September 2011, he settled down in life and married a wealthy Karchi businessman's daughter, Saniya Shaikh, who helps out in her family businesses in Pakistan and Britain.
Of Moin's siblings, Mahrukh got married in 2006 to Junaid, the son of Pakistani star cricketer Javed Miandad, and middle sister Mahreen tied the knot with a US-based businessman's son in early 2011.
Earlier, Iqbal Kaskar had revealed that Dawood is in excellent health and living in Karachi under the protective eyes of the Pakistani agencies, dismissing all speculation on his physical well-being that keeps floating occasionally.
The investigators are hopeful that in the coming days, he may reveal more information about the Godfather's family imbroglios and provide clues to the future of his activities.