He'd have some problems. My feel's that he'd lose; it's not quite impossible that he'd the primary, if Hillary didn't run, but he faced decidedly better Republican opponents, whom would've beaten him easily. Sorry!
Problems:
You have to be GOOD to win a Senate seat. And he struck me as a total lamer. And, his magazine was mediocre and losing money, a bad sign on talent, so it's not just me.
The nation's tired of Kennedies by then. It defeated another, IMHO better candidate in Maryland at a similar timeframe.
We Democrats are at best divided to anti about dynasties like the Kennedies.