Depends on the frame of reference. Could be you, Jim or neither which is a third possibility that a lot people (tea baggers? (trailer trash)) have major problems understanding.
As alluded to earlier, are there masses (heavenly bodies) that might "tinker" with trajectories? Who is "observing" the winner of the race, Jim, you or some other entity? (for instance, depending on the fact that a reflection takes time to occur, therefore, detection, Jim might never ever see a reflection, arriving at the asteroid simultaneously with his flashlight beam.) Also, how does Jim tell you that he has "lit" his flashlight, by speed of light?
I might have said it already, but, Richard Feynman, in his three volume set of lectures (available at all libraries except for red-neck dirt stupid states like Arizona and Texas) explains it much better than I.