The stability and integrity of protective coal pillars between the longwall working face and development roadways are greatly affected by the mining activities such as the development face advancing or retreat mining. Due to underground strata pressure, the coal pillar cracks could be further developed and then the air leakage passages (mainly cracks) could be produced greatly. The air circulation caused by the atmospheric pressure difference between the two sides of the coal pillar may also provide suitable conditions for the possible spontaneous combustion of the residual coal in the mine gob. In this paper, a typical the protective coal pillar in a Chinese coal mine is studied. The deformation and stress of coal pillars during the mining process of longwall working face are simulated by using FLAC^3D. The displacement and strain of coal pillars are analyzed. Two indexes, the linear fracture rate (LFR) and area fracture rate (AFR), are introduced to characterize the development of internal cracks’ development within coal pillars. By using field measurement, the air leakage intensity distribution due to coal pillar cracks is obtained; the equation of air leakage resistance of coal pillar under the influence of mining is derived. Then, the possible location of large air leakage of coal pillar is determined, which can be used as guidelines to study the possibilities of coal spontaneous combustions happening in pillar or mine gob. The research results help to control such potential hazards in advance.