In recent years, semi-arid regions of India, especially Marathwada, have been continuously under the grip of drought. Increasing water scarcity and depleting ground water levels have accentuated the agrarian crisis with an increased number of farmers committing suicide in this region. To understand this issue, the present paper deals with the roots of the drought severities concerning the summer monsoon rainfall and changing crop types over the districts of the Marathwada region, India, from 1996 to 2018. In this study, drought severities were quantified using station-based rainfall, groundwater level, and crop data (10 most cultivated crops) collected from various national agencies. The increasing rainfall trends over the Latur, Beed, and Aurangabad districts depict positive signs for agriculture. In contrast, other districts were under decreasing rainfall trends, but these declining rates were not statistically significant. The alarming fall of ground water level from 4 to 5 m during the considered period was noticed over most of the region, which is a cause for concern. The significant changes in agricultural practices from low-water-requirement crops such millet (bajra), sorghum (jowar), and wheat to high-water-requirement crops such as sugarcane and cotton were observed over Beed, Latur, Osmanabad, and Parbhani. An increase in the yield of cash crops demands an augmented water supply, which is becoming responsible for the rapidly declining ground water level. Therefore, this study claims that more than rainfall vagaries, the severe impact of droughts is a reflection of changing agricultural practices and poor management of water resources.