Complex sentence: He was one of the first broadcasters to do on-field interviews, but in later years he felt uncomfortable with announcers who frequently criticized on-field performances, having grown up in an era where sportscasters were regular drinking buddies of players and managers.
Split into simpler sentences: He was one of the first broadcasters to do on-field interviews. However, in later years, he felt uncomfortable with announcers who frequently criticized on-field performance, having grown up in an era where sportscasters were regularly drinking buddies with players and managers.