The charismatic personality of Prof. Dr. Muhammad Masood Ahmed had excellence in Islamic and Urdu literary services both. In Urdu literature, the significance of letters (Maktoobat) stands high. The letters of condolence reflect charisma of Prof. Masood's personality. Dr. Masood's letters are, in fact, an artifice of sad realities, coupled with the severeness and bitterness of death. He strived for seeking panacea for the aggrieved families by euphimizing this very severeness and providing a psychological relief for the effected ones. At one place they are letters of condolence while they are masterpieces of literature too and this respect is the core theme of this research paper in hand.