We don't really know but seeing how he nonchalantly ordered the assassination of those three guys I can safely assume that he did it many many times. Being a cop he probably used that power to kill criminals that he couldn't arrest. That before realizing it was pointless since for every criminal killed a new criminal would take their place. Kondo must have realized that police doesn't solve problems, police just tries to mend the anomalies caused by a more deeply rooted problem. That's why he said:
"At first I also tried to save this country"
"What a policeman like me can possibly do to save this rotten country?"
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