Several theories describe the development of the retraction pocket of the tympanic membrane (RP). Many authors suggest that the negative middle ear pressure is the main reason responsible for developing this condition. A narrative review has been undertaken, and conclusions are drawn reflecting a current knowledge with our new observations in the histological and immunohistochemical study. Recent studies show the important role of inflammation in the development and progression of RP. A review of the available literature shows that the inflammation plays a key role in pathogenesis of the RP and its progression to the cholesteatoma. We support this statement with our new results from histological and immunohistochemical analysis of the RPs.