Very interesting statement and here is the justification for it:
The U.S. started with no stars. In fact, it started with a completely different flag. The last two were added in 1959, Hawaii and Alaska. Until there’s a President born after ’59, that dies with no change in the flag and no change in the number of states, that will continue to be a true statement. (link)
Barack Obama was born on August 4, 1961; while George W. Bush and Bill Clinton were born in 1946. So, the first President to be born and dying under the same flag would be Barack Obama, unless US makes another territory as its state.