In the process of hard rock breaking, the conical pick bears great cutting force and wear, and the cutting efficiency is lower. Thus different combination ways of water jet and conical pick were proposed to solve this issue; for instance, water jet placed in the front of pick (JFP) and water jet through the center of pick (JCP) was researched by numerical simulation and experiments in this paper. First, the models of rock breaking were built based on SPH combined with finite element method. Then, the stress distribution of rock and the cut force of pick were analyzed when the rock broken by the conical pick assisted with the high pressure water jet. It indicates that the effect of the JCP on rock breaking is better than the JFP. At last, experiments about rock breaking with a conical pick and the JCP were conducted to verify the reliability of the simulation. It indicates that the rock breaking with the assistance of high pressure water jet cannot only reduce the pick force, but also increase the rock crushing volume.