The repeated evolution of fused carpels (syncarpy) is one of the dominant features of angiosperm macroevolution. We present results of new phylogenetic and theoretical analyses to assess the frequency and nature of transitions to syncarpy, and the possible advantages of syncarpy over apocarpy under a variety of ecological conditions. Using a recent molecular estimate of angiosperm phylogeny, we ascertained that a minimum of 17 independent evolutionary transitions from apocarpy to syncarpy have occurred; about three-quarters of these transitions allowed pollen tubes to cross between carpels and fertilize ovules that would otherwise be left unfertilized. Most of these transitions also intensified competition between pollen, potentially enhancing offspring fitness. The high proportion of evolutionary transitions promoting pollen competition and pollen-tube access to all carpels supports the hypothesis that the main advantage of syncarpy is in increasing offspring quality and quantity. The potential advantages of syncarpy were more thoroughly evaluated by analytical and simulation studies. These showed that the advantage of syncarpy over apocarpy involving increased offspring-quantity held under conditions of marginal pollination and declined with increasing pollination. The offspring-quality advantage persisted over a wider range of conditions, including under quite high pollination rates.