Having spent all of its time and energy protecting presidents from would-be assassins, it's understandable the Secret Service wouldn't be so good at protecting them from the papaparazzi. But, with Obama as big a celebrity as Brangelina, the Secret Service might want to take some pointers from Brangelina themselves. A couple years ago I wrote a piece for New York Magazine about the paparazzi's pursuit of what was then called "the Holy Grail of celebrity journalism"--i.e., the first photo of the Brangelina Baby (who now goes by the name Shiloh).
Here's a bit that went over some of Pitt and Jolie's previous tactics for foiling the paparazzi:
In 2000, when Pitt was marrying Aniston, he had a Los Angeles printer make up invitations with the wrong date and location, knowing someone at the printer would leak the information. Then, in order to thwart the photographers who discovered the wedding’s real location—which was at a friend’s Malibu mansion—and who were tempted to try to shoot the nuptials from helicopters, Pitt supposedly secured a temporary flight restriction over the property, which, as one paparazzo puts it, “is like an act of God . . . That house was like the fucking White House.”
Jolie is usually more accommodating of the shutterbugs, but she too has resorted to extreme measures. Earlier this year, for instance, when she was shooting The Good Shepherd in the Dominican Republic (just before publicly revealing that she was pregnant with Pitt’s child), the film set resembled an armed fortress. “The local security actually had the Dominican military working with them,” says one paparazzo who tried and failed to shoot Jolie (and her by then noticeably growing belly) in Santo Domingo. “If they told you something once and you didn’t do it, you were going to jail.” His local tour guide did, in fact, end up getting arrested.
Of course, Hawaii isn't Namibia, so there's only so much the Secret Service--and Obama--can do.