If the memory grant in the cached plan is 2x > the memory required, then yes, it will lower it. Any spill to disk will bump it up, so it could go up in increasing amounts. Therefore, it is possible that you could have a ping-pong effect - up to a point. If the plan has an unstable memory requirement because of the variance of parameters used, then the memory grant feedback will disable itself for that plan. You can see this with the memory_grant_feedback_loop_disabled XEvent.
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