The value of play has mainly stayed consistent throughout time. Playing is, without a doubt, one of the essential things we can do. Playing in addition to supporting motor, neurological, and social development improves adaptation by encouraging people to explore diverse perspectives on the world and assisting them in developing methods for dealing with problems in a safe setting. The way we play and what we play with have been heavily affected by the quickly evolving technology shaping our daily lives. Artificial intelligence (A.I.) is now found in many products, including vehicles, phones, and vacuum cleaners. This extends to children's items, with the creation of an "Internet of Toys." Many learning, remote control, and app-integrated toys include innovative playthings that employ speech recognition and machine learning to communicate with users. This study examines the impact of technology adoption on the success and failure of two toys industry – Hasbro, Inc and Toys R Us, Inc. The research methodology of this study is based on case studies where the comparison of the two industries was made from a few areas. The finding of the study determines that corporations that evolved consistently with the change of technology will continue to grow in the market. In contrast, the corporation that failed to adopt digital transformation will be a force out of the market.