The spread of alien plant species is a critical ecological event worldwide but the forces that control this spread are not well documented. Alien plant species are well known to disrupt ecological services of native ecosystems change the composition of native habitats and often lead to the extirpation of native flora and fauna. Here we report on life history patterns of plant species with rapidly spreading and declining ranges in North America’s major urban region. We tested for differences in life history traits between the 466 native and alien woody flora of the New York metropolitan area. We also examined the relationship between life history traits and change in distribution in the New York metropolitan area between 1900 and 2000. Native and alien species of the New York metropolitan area differ with respect to pollination vector and breeding system. However pollination vector and breeding system are not associated with success defined here as increasing range spread in the urban environment; instead fruit type (dispersal) life form and origin are important determinants of success. Alien species that are deciduous trees shrubs or vines with fleshy fruit are the most successful in increasing their distribution in this urban landscape. Newly introduced species with these characteristics are expected to have a better chance at establishing in similar urban landscapes and should be targets for intensive management. The ability to predict which alien species will become invasive is also a valuable tool for the prevention of invasions by newly introduced plant species.