For a string equation with time delays in the output feedback loop, we study stability and show that the system is a Riesz spectral system and prove that the spectrum-determined growth condition holds for all delays. When the delay is equal to the even multiples of the wave propagation time, we develop the necessary and sufficient conditions for the feedback gain and time delay which guarantee the exponential stability of the closed-loop system. In particular, we show that as the delay of even multiples is increasing to infinity, the stability bound on the feedback gain decays to zero. We also show that whenever the delay is an odd multiple of the wave propagation time, the closed-loop system is unstable. The lack of robustness to a small perturbation in time delay is specifically discussed for the delay equal to two. A numerical simulation for the case of the delay equal to two is presented to illustrate the convergence. Finally, an alternative stability analysis is conducted within the framework of well-posed infinite-dimensional systems.