But one thing appears to have outweighed all of his concerns as he reached an agreement on a four-year extension Saturday.
The 33-year-old quarterback chose to stay with the franchise he joined more than a decade ago, and the place where most of his seven children were born.
Chargers general manager Tom Telesco said he wanted to make sure that Rivers retired a Charger. And signing Rivers to a new deal goes a long way to accomplishing that goal.
The new deal, worth $83.25 million with $65 million guaranteed, gives Rivers the highest guaranteed money of any player under a current contract.
That creates some financial security for Rivers and wife Tiffany, who are expecting their eighth child.
But the move also shows Rivers is committed and believes the Chargers are built to compete for a Super Bowl now. It is a good sign for a young San Diego roster with emerging talent.
The move means that if, and when, young players such as linebacker Melvin Ingram, defensive end Corey Liuget and cornerback Jason Verrett reach their potential, the Chargers will have a franchise quarterback at the controls who's capable of leading them to a Super Bowl title.
He is, after all, the Chargers' all-time leader in wins (88). Rivers has started 144 consecutive games and since becoming a starter in 2006, only Peyton Manning (102) and Tom Brady (99) have more wins than Rivers.
In terms of the team’s potential relocation to Los Angeles, the signing of Rivers also provides a sliver of hope that the Chargers still are willing to get something done in their home market.
The Chargers potentially relocating to Los Angeles reportedly had been a source of heartburn for Rivers, who wasn’t keen on moving his family a couple of hours north. Now that he’s committed to the franchise long-term, maybe he’ll put in some work to make sure the Chargers stay in San Diego.
And there’s one obvious thing Rivers can do to accomplish that goal: lead the Chargers to a Super Bowl.