It's very rare that the band or artist are behind a Greatest Hits/Very Best Of albums anyway. The rights holders will release them and then re-release them often seasonally, because money. Columbia Records own the licensing rights to his entire discography, so can do what they want with it. Bruce probably gets a cut, or he might have sold the rights to it all as a job lot, which is not uncommon but he'd be silly to do that, unless it was stupid money. I'd doubt Bruce himself gets his label on the phone to tell them "it's time for another Best Of. You know what to do". As they hold the licensing rights, Columbia could release a new Best Of every week if they wanted, and there'd be little he could do about it. A lot of artists have spoken about this happening. Paul Weller in particular gets annoyed about Polydor continuing to release compilations and "deluxe" versions of albums by The Jam, but they own the rights to it all, Weller agreed to it, he can't do anything. They could release it on a SNES cartridge or a floppy disk if they wanted, it's their content.
That said, after looking it up, Springsteen only has two official "Greatest Hits" albums, released nearly 15 years apart. Looking at the rest of the compilation albums, they're all very different, with lots of unreleased and alternate versions of songs from different eras and recording sessions.
Either way, it's not fleecing fans. Fans have the choice to buy it. If they look at the track listing and see they've got the majority of the material on a compilation, they can choose not to buy it. Greatest Hits albums aren't really aimed at fans anyway, but people who like 2 or 3 songs they've heard on the radio.