Whateley started his media career at the Herald Sun newspaper. He spent six years at the Herald Sun in which he gained experience including police rounds, courts and state politics. Whateley was also involved in the research of the Herald Sun's hardback book Our Home Front, documenting life in Australia during the Second World War from the newspapers of the time. Whateley became the paper's movie writer, then editor of HIT magazine (the Herald Sun's movie and music lift out), prior to being appointed senior writer for the newly released Sunday Magazine in 1998. Whateley travelled to the US and Europe, interviewing some of the world's famous people including Steven Spielberg, Leonardo DiCaprio, Kevin Spacey, Morgan Freeman, Geoffrey Rush, and Cindy Crawford. During this time, Whateley was heard for the first time on the ABC with a weekly segment reviewing videos on the afternoon program.
Whateley began to focus more on sports, writing regular in-depth features and gaining access to the likes of Wayne Carey, Greg Norman, Damien Oliver and Jacques Villeneuve along with covering football as a "second job" for the Sunday Herald Sun.
At the beginning of 1999, Whateley took up the job as the network's Senior Sport Reporter for Channel Ten. His chief responsibilities were to cover the AFL scene and horse racing. At the completion of his first year, Whateley was named the Young Journalist of the Year at the Melbourne Press Club's Quill Awards. He was also named the Network Ten Young Achiever of the Year from nationwide consideration of employees. Whateley earned a reputation for authority and accuracy, enhanced at the 2000 Olympics breaking a series of stories surrounding the drug use by competing weightlifters.
In 2001, Whateley accepted the chief reporter's position at Seven News, winning the Quill Award for the Most Outstanding News Report for an investigation that revealed a wanted US criminal had lied to enter Australia to win a Melbourne radio station's Valentine's Day competition.
Soon after, Ten reclaimed Whateley's services to be a foundation member of the network's AFL commentary team. He later joined ABC Radio's AFL team, and in his inaugural year calling football, Whateley was named the Australian Football Media Association's Most Outstanding Radio Caller, following in the footsteps of Tim Lane. Throughout this time, Whateley's horse-racing work in print, radio and television was rewarded with numerous awards, including the 2004 Cox Plate Story of the Year for the ABC.
Having been a regular voice on the national broadcaster for a couple of years, Whateley joined the ABC full-time in September 2004, to fulfill a childhood dream of broadcasting a wide variety of sports. He calls tennis, Australian rules football, soccer and horse racing.
Whateley was a regular panelist on the ABC's Sunday morning sports show Offsiders, and is the program's acting presenter while Barrie Cassidy is on extended leave. He is also the co-host of Fox Footy's weekday program AFL 360 (2010– ), alongside Herald Sun football journalist Mark Robinson.
- Gerard Whateley. Grandstand Tennis
- Brady, Nicole (24 March 2005). "A true calling". www.theage.com.au. Retrieved 5 May 2017.