Several studies on cognition, molecular phylogenetics and taxonomic diversity independently suggest that Darwin's finches are part of a larger clade of speciose, flexible birds, the family
Thraupidae
, a member of the New World nine-primaried oscine superfamily
Emberizoidea
. Here, we first present a new, previously unpublished, dataset of feeding innovations covering the Neotropical region and compare the stem clades of Darwin's finches to other neotropical clades at the levels of the subfamily, family and superfamily/order. Both in terms of raw frequency as well as rates corrected for research effort and phylogeny, the family
Thraupidae
and superfamily
Emberizoidea
show high levels of innovation, supporting the idea that adaptive radiations are favoured when the ancestral stem species were flexible. Second, we discuss examples of innovation and problem-solving in two opportunistic and tame Emberizoid species, the Barbados bullfinch
Loxigilla barbadensis
and the Carib grackle
Quiscalus lugubris fortirostris
in Barbados. We review studies on these two species and argue that a comparison of
L. barbadensis
with its closest, but very shy and conservative local relative, the black-faced grassquit
Tiaris bicolor
, might provide key insights into the evolutionary divergence of cognition.