In species in which males defend territories for breeding, males may differ in territorial behavior; alternative behaviors among territorial males are not well understood. In our long-term study of partially-migratory song sparrows, we have observed that most territorial males establish territories before females begin nesting and remain site-faithful both within and between breeding seasons; however, some males establish territories later in the season (late establishers) and/or change territory locations either within or between seasons (movers). Whether late establishment or moving are equally successful strategies for territory defense, or best-of-bad-job options, is not known. Here, we compare the frequencies of these behaviors to demographic variables over a 9-yr period and compare lifetime tenure and early season nesting success for males who differ in site fidelity and timing of territory establishment. Across years, late establishing was negatively correlated with the return rate of previously territorial males; moving was positively correlated with the number of occupied territories at the start of the breeding season (territory density). While moving was independent of number of years on territory, late territory establishment only occurred in a male’s first year as a territory holder. Of 88 males, 25% established their first territory late, primarily in undefended space; 31% moved. Late and early establishers did not differ in lifetime tenure; movers, however, had longer lifetime tenure than site-faithful males. Among early establishers, movers and non-movers did not differ in the number of successful early nests/year or number of young fledged/year; among late establishers, however, movers had significantly higher early nesting success by both measures. Late establishers who moved had higher early season nesting success and higher early season nesting success/year than site-faithful early establishers. Thus, individual variation in the timing of territory establishment and site fidelity may be facultative alternative territorial strategies.