The name of the game: X-ray crystallographic analysis of Gilman- and Lipshutz-type amidocuprates indicates that the presence of LiX (X=CN, I) and THF shifts the equilibrium between the two toward the Lipshutz-type cuprate and that this is important in generating the active species for directed ortho cupration. DFT calculations show that monomeric Gilman-type cuprates have an unprecedentedly high reactivity (see scheme, DG=directing group). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.