What do John Elway, Isiah Thomas, and Larry Bird all have in common?

They did what Chauncey Billups desires to do now: run a team from the front office after having a successful career playing.

The King of Park Hill has always been a favorite in Colorado, dating back to his days at the University of Colorado at Boulder. The former Denver Nuggets point guard and NBA Finals MVP (with Detroit) has always been an exemplary player and human being to come out of Colorado, and because of it, many Nuggets fans have become attached to him.

A large faction of fans on Denver Stiffs and in the community have expressed an interest in bringing Billups back into the fold. Many would love for him to coach and share his wisdom that way, but some want him to take control of basketball operations as the general manager or a similarly powerful role. Whether this is wise is up for debate, but the fact remains that Billups is willing to enter the Nuggets organization if he’s allowed certain freedoms in running the team.

Before getting into whether this is a good idea, here’s some history of the three guys I mentioned above (Elway, Thomas, and Bird) and how each of them entered the sports business.

After fading into the sunset with two super bowl trophies in early 1999, John Elway became the co-owner of the Colorado Crush, an Arena Football League team, in 2002. For six years, he developed as an owner and operator of the team. By 2007, Elway was elected Chairmen of the AFL’s executive committee. On August 4th, 2009, the committee decided to shut down AFL operations, but during those years, Elway became a skilled business man. He also opened multiple restaurants, auto dealerships, and other business ventures.

His experience managing people and completing major business goals continued to prepare him for the big leagues of the NFL, but he didn’t assume full responsibilities even when he was hired by the Denver Broncos in 2011. He came in as the president of football operations, but Brian Xanders remained the general manager of the team while Elway grew accustomed to the role. After a year, he assumed full general manager responsibilities as well, and his first major move was to bring in Peyton Manning to play quarterback. Since he assumed full responsibility, the Broncos have been to two super bowls and won once in four years, so he’s clearly been successful in the role.

Next, Isiah Thomas is MUCH less of a cheery executive to talk about. After his playing career with the Detroit Pistons, he also took up some business ventures, but few of them basketball related. His three major experiences before becoming a general manager were all negatives. He became part owner and executive vice president of the Toronto Raptors from 1994-1996, but he left the team when he had a dispute with management about the team’s direction and his future role. He purchased the Continental Basketball Association in 1998, and while he made some interesting movements forward with the league, it collapsed due to bankruptcy in 2001 (the CBA later became the NBA Developmental League). Finally, Thomas coached the Indiana Pacers from 2000 to 2003, but the sense around the team was that Thomas help the team back due to inexperience and ineptitude coaching. Larry Bird returned to the organization and fired him, replacing him with Rick Carlisle.

This leads into Thomas’ tenure as the general manager of the New York Knicks, and it was not a good one. While the pressure to win-now is always high in New York, Thomas made many boneheaded mistakes. He traded away a bundle of draft picks for Eddy Curry, two of which became Joakim Noah and LaMarcus Aldridge. He traded for Zach Randolph in desperation and gave large contracts away at will. His managerial decisions and acquisitions of over-the-hill stars in exchange for valuable draft picks set the Knicks back for years, and Thomas was banned from the team because of it.

Larry Bird is the final player turned executive I will be talking about. Remember when I talked about Bird coming in and firing Thomas? Yeah, he hired Carlisle, and the Pacers went to the playoffs for three straight years before a four year drought. Bird became the president of basketball operations for the Pacers, and he flourished in the role for the most part. Injuries, Malice at the Palace, and bad attitudes ruined the rest of the 2000s for the Pacers, but they recovered nicely with the drafting of Paul George. Bird came into the role with little experience, and he was (and still is) up and down throughout his tenure. He has struggled with the draft, but has made up for it by hitting on gems like Danny Granger, Paul George, and assumably Myles Turner. He hasn’t recruited free agents very well though, as his best acquisition has been David West.

These are the polar opposites of players running teams. One had major success (Elway), one had zero success (Thomas), and the other had moderate success (Bird). It brings us back full circle to Billups, who’s expressed interest in going the Larry Bird route. This route designates a player who immediately moves into the front office without any previous business experience. It’s possible it could work, but it’s also possible it could crash and burn.

The belief is that Billups, as a former NBA player, would establish a presence in the front office of the Nuggets which would help elevate their profile around the league. This would then lead to more free agents expressing an interest in Denver as a destination.

The other side of the coin is that recruiting free agents is just one of the roles a general manager has to balance. If Billups were to be given complete control, he would be responsible for drafting new players and making trades as well, two aspects that would be very new to him. He might have success, and he might not.

Current general manager Tim Connelly has an outstanding draft record at this point in his tenure with the Nuggets, having selected a number of quality rotation pieces and potential cornerstone players. He has also made shrewd trades, collecting assets and turning nothing into something on a fairly annual basis. He certainly made his mark in those aspects, but the one aspect he has struggled with is the one Billups may be the most helpful.

The Nuggets have not recruited any major free agents during Connelly’s tenure. Much of that has to do with the salary cap situation he was left with and the fact that Denver has never been a big draw for free agents. The Nuggets surprised everyone last summer when they made the short list to land free agent Dwyane Wade. Connelly and company made a good impression on Wade but didn’t close the deal. Wade is currently contributing to a surprisingly strong Chicago Bulls team, and it would have been nice to have him to close games and be a consistent first option for the team.

So, what should the Nuggets do? Stay the course and keep Connelly in his role, or change the makeup of the organization by adding Billups? There is a third option, presented by Matt Moore of CBS Sports, to reconfigure Josh Kroenke’s role with the team to keep Connelly and Billups. Here’s Moore’s perspective from back in June:

“It wouldn't make a lot of sense to demote or move Connelly, who's done a great job, and just received a multiyear extension last winter. Team President, however, makes a lot of sense. Owner Josh Kroenke is the current holder of that title, but his interests are spread across the various Kroenke Sports holdings, including Premier League club Arsenal. Kroenke will always hold a voice in the organization, but it would be easy to move Kroenke to some other title and slide Billups into "President of Basketball Operations." Connelly would handle the day to day and oversee the draft, and Billups would hold a voice in the room and help to recruit free agents, the biggest talent he could bring.”

That last part is important. If Josh Kroenke is willing to cede his title to Billups, and if Billups is willing to ease into the role by simply being a recruiting voice in the organization and working with Connelly, then the fit could work out. There are difficult dynamics that would have to be smoothed out, but if everyone makes sure to “stay in their lane,” then the dividends would be special.

My personal opinion is that Tim Connelly has done an excellent job overall for the Denver Nuggets. After a few bumps in the road, he’s managed to build an exciting, young team brimming with talent at every position. The next step is to make a major move to certify the direction the Nuggets want to go. Billups could certainly be helpful with that, and he might even be better for the job, but the unpredictability of handing him the reins scares me. Bird has done…okay in this regard, and Billups certainly may as well. I see value in adding him into the organization, but giving him complete control is just as likely to lead to an Isiah Thomas situation as it is a John Elway situation.