Who should replace Alex Trebek when he leaves Jeopardy? It's the $5,000 question to an answer that we're yet unsure about, but there are some names swirling in the ether after Alex Trebek told CNN he may be leaving Jeopardy in 2020. Or rather, he told TMZthere is a 50/50 chance that he may be leaving in two years time. So... these two people could be replacing Trebek.