For years, Chauncey Billups has envisioned himself working in an NBA front office.
But when the 40-year-old, five-time All-Star was presented with his first opportunity, he apparently decided the timing, circumstances and the Cavaliers' checkered front office history were not right.
ESPN's Adrian Wojnarowski reported that Billups took his name out of consideration to become the Cavs' head of basketball operations on Monday, pondering the decision for 11 days after meetings with owner Dan Gilbert in Detroit and Cleveland.
The Athletic reported Billups was offered a five-year contract on June 21.
"I have great respect for Dan Gilbert and the Cleveland Cavaliers, and I greatly appreciate the discussions we had regarding their organization," Billups told ESPN. "As I have conveyed before, ultimately I would like to lead a team's basketball operation and be a part of a successful franchise. But presently, the timing just isn't right to delve into that role in Cleveland. In the meantime, I will continue to focus on broadcasting and my other business endeavors."
Wojnarowski reported that Gilbert and Billups had gone back and forth for over a week, but they never could come to an agreement on the parameters of the job. Billups told ESPN he informed Gilbert of his decision Monday morning.
Gilbert offered Billups between $2-$3 million annually and Billups wanted more, according to Cleveland.com's Joe Vardon. Former GM David Griffin was reportedly one of the league's lower paid executives with the Cavs, making less than $2 million. Vardon also reported that Billups never spoke with LeBron James or his agent, Rich Paul.
Billups has been an ESPN analyst since he retired after the 2013-14 season. He has found it a comfortable commute between his home in Denver and network headquarters in Los Angeles. According to ESPN's Brian Windhorst, Billups' daughter will be a senior in high school next year, also a factor in the decision.
Windhorst said on a recent podcast that he had a long conversation with Billups about the Cavs job during the Finals as it became more apparent that Gilbert would part ways with Griffin, a split that took place on June 19.
According to Windhorst, Billups did not fear the fact that four-time league MVP James can be a free agent after next season. But there were several other reasons Billups may have balked at the job.
What he probably feared most was the string of short-lived general managers under Gilbert. In 12 years, four men have held that title and none has received a contract extension.
Gilbert may have thought that wouldn't be an issue with Billups, whom he's known for over a decade since Billups endorsed Gilbert's then-Rock Financial while a member of the Detroit Pistons. Billups has no front office experience, but was Finals MVP in 2004 when the Pistons won the championship.
But Gilbert is a hands-on owner, which contributed to Griffin's departure and likely Billups' decision as well.
Billups played in Ice Cube's BIG3 three-on-three league Sunday in Charlotte, where he may have discussed the Cavs' opening with his peers.
Billups and Gilbert talked June 20 in Detroit and June 21 in Cleveland. The Athletic reported that included a trip to Quicken Loans Arena, where Billups met executives who would serve under him.
According to Windhorst, Gilbert approved Billups' hiring of an experienced general manager to assist him.
It was not Billups' first such interview; he recently talked to the Atlanta Hawks about a front office position.
Billups is close friends and shares the same agent with Cavs coach Tyronn Lue. However symbiotic that partnership might seem, becoming the team's basketball chief could have put a strain on their relationship.
The Cavs seek to retool their roster to defeat the Golden State Warriors, who have beaten them in two of the last three NBA Finals. The Cavs won the city's first championship in 52 years in 2016.
Moves like the Los Angeles Clippers' agreed-upon trade of Chris Paul to the Houston Rockets before Saturday's start of free agency showed that the league's playoff teams are ramping up the race for talent in pursuit of the Warriors. Meanwhile, the Cavs were unable to complete any trades on draft night June 22 with one of their targets, the Chicago Bulls' Jimmy Butler, going to the Minnesota Timberwolves.
Since then, the Indiana Pacers traded another player who piqued the Cavs' interest, Paul George, to the Oklahoma City Thunder.
After the departure of Griffin and senior vice president Trent Redden, whose contacts were set to expire on June 30, assistant general manager Koby Altman became second in command behind Gilbert. Gilbert could choose to promote Altman like he did with Griffin and his predecessor, Chris Grant.