Billups has yet to accept the offer to serve as the Cavaliers' president of basketball operations.
USA Today's Sam Amick broke down why Billups has not put pen to paper on a deal:
The Associated Press (via USA Today) reported Wednesday that Billups spent a second straight day meeting with Cavaliers owner Dan Gilbert to discuss the opening.
The Cavaliers have been in search of a new general manager and face for their front office since David Griffin parted ways with the defending Eastern Conference champions on Monday.
Should Billups, 40, accept the Cavaliers' proposal, he will immediately be under pressure. The Cavaliers enter a critical season that could determine the future of the franchise.
As things stand, LeBron James has the ability to opt out of his contract after the 2017-18 campaign, and indications are he'll consider his options on the open market next summer.
Billups would also have to navigate the trade market and try to improve the Cavaliers roster for the short term so it's better positioned to compete with the Golden State Warriors should they meet in the NBA Finals for a fourth straight year.