That is mature, rational, considered, and completely wrong. What's exposed here is not a failure of process or education, its the fact that controller is an incompetent idiot who never should have been acting in a life critical capacity.
In the linked communication you can see that he knew both planes were incoming on the same runway and confirmed his brain dead plan repeatedly to both crews. Even telling SW that they could take off because Fedex was 3 miles out. At any reasonable speed this is virtually no time. At 165 it would be a little over 1 minute. Since the critical moment came around the 2 minute mark it seems likely that in addition to any other faults he also can't estimate distance.
Even after it went south or shall we say southwest he was never capable of recovering in any timely fashion as evidenced by the Fedex crew taking over his job. As a result of his incompetence everyone would have died. The only meaningful fact he could have ascertained in order to correct his plan would have been to understand that planes go fast. At this juncture retraining him seems like a poor decision. He's a hazard.