The dynamics of food consumption by higher trophic level is complicated as its availability, choice, and consequently their development. The top predator interference has a strong influence on the dynamic structure of the tritrophic food chain system. The proposed article deals with the characteristic features of a three‐tire modified Leslie–Gower model with a one‐prey two‐predator system with the assumption of multiple gestation delays. The intermediate predator of the food chain is taken as a specialist type, whereas the growth of top predator is assumed by sexual reproduction. Two different response functions named Monod–Haldane (M‐H) and Beddington–DeAngelis (B‐D) are considered for the modeling of system dynamics. The population densities of intermediate and top predators are assumed to be affected by two different gestation delays. The boundedness and positive equilibria and their stability conditions are examined theoretically for the delay‐free system. The local and global stability conditions of the delayed system are also determined. With the help of normal form theory and central manifold arguments, the properties of bifurcating periodic solutions are carried out. The numerical computation is performed to validate our analytical findings that show the different dynamical outcomes such as periodic and chaotic dynamics. The Hopf‐bifurcation scenario for different parameters of the model system is well studied. Further, the stability behavior of multiple delays for the different cases is investigated. The system shows chaotic behavior when the gestation delay of intermediate predators is large enough. It is also observed that the top predator density is highly fluctuating through the creation of chaos by the inclusion of time delay. Finally, the time delay destabilizing effect is noticed for three‐way interactions among prey, intermediate predator, and top predator, highlighting its significance in chaotic dynamics.