Coal pillar stability is strongly influenced by the site-specific geological and geotechnical conditions. Many geological structures such as faults, joints, or rock intrusions can be detrimental to mining operations. In order to evaluate the performance of coal pillars under weak roof degraded by igneous rock intrusion, stress and deformation monitoring was conducted in the affected tailgate areas of Nos. 8208 and 8210 longwalls in Tashan coal mine, Shanxi Province, China. The measurements in the 8208 longwall tailgate showed that the mining-induced stresses in 38-m-wide coal chain pillars under the overburden depth of 300–500 m started to increase at about 100 m ahead of the 8208 longwall working face and reached its peak level at approximately 50 m ahead of the longwall face. The peak stress of 9.16 MPa occurred at the depth of 8–9 m into the pillar from the tailgate side wall. In comparison, disturbance of the headgate block pillar area was negligible, indicating the difference of abutment pressure distribution between the tailgate and headgate sites where the adjacent unmined longwall block carried most of the overburden load. However, when the longwall face passed the headgate monitoring site by 360–379 m, the pillar stress increased to a peak value of 21.4 MPa at the pillar depth of 13 m from the gob side mainly due to stress redistribution in the chain pillar. In contrast to the headgate, at the tailgate side, the adjacent goaf was the dominant triggering factor for high stress concentrations in the chain pillar. Convergence measurements in the tailgate during longwall mining further indicated the evolution characteristics of coal pillar deformation, clearly showing that the gateroad deformation is mainly induced by the longwall extraction it serves. When predicting the future pillar loads from the monitored data, two stress peaks appeared across the 38-m-wide tailgate coal pillar, which are separated by the lower stress area within the pillar center. This 10-m-wide elastic pillar core area indicates that the coal pillar may be narrowed to 30 m to improve coal recovery. The measurements further indicate that, if the headgate of the next panel can be developed after the adjacent gob becomes stable, the coal pillar width may be further reduced to 20 m. This study is applicable for the chain pillar design, the gateroad secondary support design ahead of the longwall mining face, and the gateroad preparation of the next longwall panel under similar geological and geotechnical conditions.