We obtained the charts of 183 patients (197 ears) who had undergone surgery for chronic otitis media (COM), and we reviewed their otic histories to analyze the series of events that ultimately culminated in surgery. All ears had originally been treated for otitis media with effusion (OME); 125 ears had been treated with tympanostomy tube placement, and 72 ears had been treated with conservative measures. Our goal was to compare the influence that these two strategies had on the subsequent development of COM and its sequelae (i.e., retraction pockets, tympanic membrane perforations, and cholesteatomas) and thereby determine which strategy is preferable. We found that although retraction pockets developed in a significantly higher proportion of the tympanostomy-treated ears than the conservatively treated ears (58 vs. 35%; p < 0.01), a significantly greater percentage of retractions in the tympanostomy-treated ears were mild and situated in the anterior part of the tympanic membrane (52 vs. 32%; p < 0.05). Moreover, severe retractions were significantly more common in the conservatively treated ears (40 vs. 16%; p < 0.02); the incidence of complete retractions in the two groups of ears was similar (tympanostomy: 32%; conservative treatment: 28%). Cholesteatomas developed in a significantly lower percentage of tympanostomy-treated ears (67 vs. 81%; p < 0.05), and the incidence of large cholesteatomas that involved the tympanic and mastoid cavities was likewise significantly lower in these ears (44 vs. 69%; p < 0.05). There was no significant difference in the incidence of tympanic membrane perforations. Finally, even though all of these ears eventually required surgery for COM, the tympanostomy-treated ears required significantly fewer repeat surgeries (16 vs. 28%; p < 0.05) and significantly fewer radical modified tympanomastoidectomies (30 vs. 44%; p < 0.05). Therefore, we conclude that myringotomy with insertion of tympanostomy tubes to treat OME is superior to conservative treatment.