After the Winter Soldier shot out Howard’s tires and caused his car to crash, he walk up close to finish the job.
Howard recognizes him and realizes just how deep HYDRA has gone.
In his last words he begs Bucky, “Please, Barnes, not my son.”
Bucky shoots him.
But from here after, anytime HYDRA attempt to send him to kill Tony, Bucky would go berserk. Until finally HYDRA just stop trying to send the Winter Soldier after Tony Stark.
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