One thing people seem to get hung up on when remembering the golden rule of “longest matching route wins” is when looking at directly connected routes.
Consider the following network from the perspective of R1:
Assume that from R1 we ping 192.168.2.2, does the ping follow the static route or the directly connected route? Remember the AD of static routes is 1, and directly connected routes have an AD of 0.
Here’s R1’s routing table.
Let’s find out the answer via “show ip cef 192.168.2.2”