ABSTRACT Recent studies using Gaia DR2 have identified a massive merger in the early history of the Milky Way (MW) whose debris is dominated by radial and counterrotating orbits. This event, dubbed the Gaia-Enceladus/Gaia-Sausage (GE/GS), is also hypothesized to have built the majority of the inner stellar halo. We use the cosmological hydrodynamic simulation Illustris to place this merger in the context of galaxy assembly within lambda cold dark matter. From ∼150 MW analogues, $\sim \!80 {{ \rm {per\ cent}}}$ have experienced at least one merger of similar mass and infall time as the GE/GS. Within this sample, 37 have debris as radial as the GE/GS, which we dub the ancient radial mergers (ARMs). Counterrotation is not rare among ARMs, with $43 {{ \rm {per\ cent}}}$ having $\gt 40 {{ \rm {per\ cent}}}$ of their debris in counterrotating orbits. However, the compactness inferred for the GE/GS debris given its large radial orbital anisotropy, β, and its substantial contribution to the stellar halo are difficult to reproduce. The median radius of ARM debris is r*,deb ≃ 45 kpc, while GE/GS is thought to be mostly contained within r ∼ 30 kpc. For most MW analogues, few mergers are required to build the inner stellar halo, and ARM debris only accounts for (median) $\sim \!12 {{ \rm {per\ cent}}}$ of inner accreted stars. Encouragingly, we find one ARM that is both compact and dominates the inner halo of its central, making it our best GE/GS analogue. Interestingly, this merger deposits a significant number of stars (M* ≃ 1.5 × 109 M⊙) in the outer halo, suggesting that an undiscovered section of GE/GS may await detection.