Kaimakoglou is considered a late bloomer, partly because he debuted with the senior national team at the age of 26 and partly because he joined one of the two traditional Greek powerhouses, Panathinaikos, at 27. The reliable power forward none the less was an integral part of the U20 Greek side that won the gold medal in the European Championship for Young Men of 2002, alongside Zisis, Spanoulis and Bourousis. He has never stayed at a club for a period shorter than two years and that stability helped him mark continuous progress as a player. His passing has improved admirably in the last years and he provides the option to run plays through him from the high-post. Kaimakogou always had a strong presence in the paint and can defend players bigger than him, while on offence he can play with his back to the basket or shoot from long range.