Gregory finds his greatest inspiration in the simple beauty of the natural landscape. Originally trained as an architect, he received his training in drawing and painting at the Honolulu Academy of Arts under Anthony Lee, George Woollard, Chuck Davis, Helen Iaea, and Mark Norseth. He was also trained at the Grand Central Academy of Art under Jon de Martin, Scott Waddell, Colleen Barry and Joshua La Rock. He also studied with nationally known artists Lorenzo Chavez, Richard McKinley, Albert Handel, Daniel Greene, Maggie Price, Greg Biochini, Terry Ludwig, and Alan Flatmann.
Gregory is a Signature Member of the Pastel Society of America and the Pastel Artists of Hawaii. He recently won Best in Show at the 2011 and First Prize in the 2010 and 2009 Pastel Artists of Hawaii Juried Competition. He won Fourth Place in the Landscape Division of the 2010 Annual Pastel Journal Pastel 100 Competition and was a featured artist in the Pastel Journal April 2010 Issue. He previously won Second Prize in the 2007 competition and Third Place in the 2006 competition. He was also a semifinalist in the 2007 American Artist Magazine 70th Anniversary Art Competition in the Pastel Category.
His greatest influences in landscape painting include: Jean-Baptiste Camille Corot, Frederich Edwin Church, and other painters of the Hudson River Valley School, as well as George Inness, Thomas Moran, Albert Bierstadt, William Metcalf, Edgar Payne, and contemporary artists, Elizabeth Mowry, Tula Telfair, and Clyde Aspevig.
Gregory worked formerly as Chief Economist for First Hawaiian Bank and Special Assistant for Economic and Policy Affairs in the administrations of Governor John Waihee and Governor Benjamin Cayetano.
He is currently represented at the Nohea Gallery at Kahala Mall and the Manoa Gallery at 2962 East Manoa Road, Honolulu, Hawaii.