Adding matter of mass m, in the fundamental representation of SU(N), to N=4 supersymmetric Yang-Mills theory, we study ``generalized quarkonium'' containing a (s)quark, an anti(s)quark, and J massless (or very light) adjoint particles. At large 't Hooft coupling $\lambda$ >> 1, the states of spin <= 1 are surprisingly light (Kruczenski et al., hep-th/0304032) and small (hep-th/0312071) with a J-independent size of order $\sqrt{\lambda}/m$. This ``trapping'' of adjoint matter in a region small compared with its Compton wavelength and compared to any confinement scale in the theory is an unfamiliar phenomenon, as it does not occur at small $\lambda$. We explore adjoint trapping further by considering the limit of large J. In particular, for J >> $\sqrt{\lambda}$ >> 1, we expect the trapping phenomenon to become unstable. Using Wilson loop methods, we show that a sharp transition, in which the generalized quarkonium states become unbound (for massless adjoints) occurs at $J \simeq 0.22 \sqrt{\lambda}$. If the adjoint scalars of N=4 are massive and the theory is confining (as, for instance, in N=1* theories) then the transition becomes a cross-over, across which the size of the states changes rapidly from ~$\sqrt{\lambda}/m$ to something of order the confinement scale ~ $\Lambda^{-1}$.