I am just wondering if, despite his teary face, J/D might be at the roadblock with T/K FIRST. Maybe Justin is just super emotional about trying to get into the finals, and got stressed out while the others were all doing the other detour, leaving him to freak out about not knowing where they stood.
So, J/D finish the roadblock first, but T/K have problems, thus T/K are still there when K/J and C/L arrive.
J/D do appear to be waiting out a penalty at the pit stop, so I am considering that maybe C/L arrive second, but win the leg (that would explain his expression), then K/J arrive third, finishing second. J/D finish out penalty, and are being checked in when T/K arrive last?
Just a theory, trying to see what else is possible.