Due to the change of ground stress environment caused by underground coal mining, the intense lateral mining stress concentration is formed around the stope; so section coal pillar is generally set up to bear the mining pressure, but the different sizes of coal pillars have obvious influence on the bearing capacity of those pillars and the characteristics of mining pressure. Mastering the mechanism characteristics by which coal pillars bearing capacity and mining stress distribution is crucial to identify the reasonable coal pillar size and give full play to the bearing role of section coal pillar, given their importance for the safety and bearing stability of engineering rock mass in underground coal mining. Therefore, the bearing characteristics of section coal pillar and the redistribution of mining stress are achieved with a mechanical model analysis on the basis of the analysis of coal pillar bearing and mining influence characteristics. Moreover, applying the elastic-plastic mechanics theory revealed the mechanical equations of the effective bearing size of coal pillar and redistribution of mining stress in longwall face. Combined with the analysis of a specific engineering example, the research results are as follows. During a roadway excavation, the continuous mining stress transfer occurs “stress redistribution” and the mechanical failure of bearing coal pillar consists of lateral mining and roadway side failures. The bearing coal pillar has two critical dimensions (i.e., the critical dimension W e of the self-bearing stability coal pillar and the critical dimension W p of failure through the coal pillar). The mechanical state of the lateral mining stress redistribution and bearing coal pillar is divided into the three situations: ① when the width of coal pillar W < W p , only one stress concentration area exists, the bearing capacity of the coal pillar is invalid at this stage, and the lateral mining stress concentration transfers to the roadway solid coal side; ② when the width of the coal pillar W e ≥ W ≥ W p , two stress concentration areas appear at this stage, and the coal pillar is in the critical state of self-bearing stability; ③ when the width of the coal pillar W > W e , three stress concentration areas are present, and the coal pillar at this stage is in a self-bearing stable state. Among all these factors, only the size of coal pillar is completely controllable, so the aspects of safe bearing and reserved size design of coal pillar, after estimating the critical size of coal pillar, the coal pillar size design is carried out according to the mine pressure control needs of mining engineering, and the cohesion, internal friction angle, interlayer friction coefficient, and coal seam mining height are improved by artificial technology, so as to realize the resource safe and efficient mining of all kinds of coal seam mining conditions; in the calculation of wide coal pillar size, the advance mining stress concentration at the end of the self-working face should be taken as the mining load condition, and the reserved size meets the condition of W > W e , thereby ensuring the stable bearing of the wide coal pillar despite the advanced mining stress concentration during the self-working face mining; in the calculation of narrow coal pillar size, the lateral mining stress concentration before mining should be taken as the mining load condition and the reserved size meets the condition W < W p , thereby realizing the effective transfer of mining stress concentration to the roadway solid coal side.