To research the internal load transfer behavior and failure mechanism of a bird’s nest anchor cable anchoring structure based on a pull-out test, a bond-slip failure model is established on the basis of statistical damage theory, and the distribution formula of shear stress at anchorage agent–rock interface is deduced. Combined with theoretical analysis, bird’s nest anchor cable pulling out test and particle flow code (PFC) numerical simulation test, as well as axial force distribution of the cable and shear stress distribution of its interface, help reveal its load transfer behavior and failure mechanism. Results show that: (1) The established bond-slip model can reflect the internal load transfer behavior and failure process of bird’s nest anchor cable anchorage structure. (2) The shear stress of the anchorage agent interface increases exponentially to the peak value and then decreases exponentially to the residual strength. The process is repeated at every location of the anchorage agent interface. The curve of the axial force and shear stress of the bird’s nest anchor cable is a negative exponential distribution with anchorage depth, and the maximum value occurs at the load end. (3) The crack of the anchorage agent interface extends from the load end to the other end and finally cuts through the whole interface. Rock mass generates radial cracks by the split effects of the bird’s nest. The failure mode is a combination of the debonding slip of the interface and the shear failure of the rock mass. The shear stress distribution and failure mode of the anchor structure are basically consistent according to laboratory tests and simulation tests, and PFC2D better reflects the internal load transfer behavior, failure mechanism, and failure process of the bird’s nest anchor cable under tensile loads.