The article analyzes system-related contradictions inherent to the development of the Russian labor law branch in XIX—XX. By means of historical-legal, comparative, dialectic methods the author investigates the roots of modern problems in law-making and law enforcement in legal regulation of hired labor relations. The author reveals negative factors in the development of the labor legislation, that are common for Russia and world leading countries. Among main evolutional problems in labor law, the author considers excessive centralization, a high degree of the right enforcement formalization, susceptibility of the branch to political environment, an important role of non-legal regulators of labor relations, low development level of security arrangements for labor rights, inadequate government supervision, a division of employees and employers’ interests, that is not always correct. The author draws the conclusion about the implicit, objective nature of the described defects and notes an essential impossibility to overcome them.