On Monday, May 22, 2023, Carmelo Anthony announced his retirement from the NBA. The national championship-winning Syracuse star played 19 seasons in the NBA for six teams and scored 30,203 points, good for 12th in league history. Anthony has had a stellar career, but he’s never won a championship in the pros, and his journey in the NBA is filled with “what if?”
There are four main “what if?” Moments from Anthony’s career. If any of these situations turned out differently, they would change not only the superstar’s trajectory but NBA history.
Here are these four burning questions about Carmelo Anthony, in chronological order.
1. What if Carmelo Anthony’s Detroit Pistons took on Darko Milic?
After winning a national championship as a freshman at Syracuse, Carmelo Anthony was the consensus No. 2 pick in the star-studded 2003 NBA draft behind generational high school star LeBron James.
However, the Detroit Pistons, second overall in the draft, won thanks to an ill-advised trade in 1998.
That season, the Vancouver Grizzlies traded then-disgruntled veteran Otis Thorpe and the Pistons’ protected first-round pick for Bobby Hurley, Michael Smith, and Chris Robinson. After five years, the pick did not transfer, and was only protected by the #1 overall pick in the 2003 draft.
The Grizzlies — who have since moved to Memphis — actually jumped into the top three with the sixth-best odds for first place. When the Grizzlies came up with a #2 card, the pick was moved to the Pistons.
Detroit was a veteran team at the time, and they won the NBA title the following season. The team needed a striker who was bigger than just a small forward with Taishawn Prince on the list. General manager Joe Dumars fell in love with Serbian teenager Darko Milicic after a serendipitous tour of John Jay College in Manhattan.
The Pistons took Milicic, Anthony fell to the Nuggets at third, and the rest is history.
But while Milicic has become one of the most popular NBA draft picks, what would Carmelo’s career be like if he went to Detroit? Was Larry Brown going to bury him on the bench like Darko? Or would he become a valuable piece of a competitor that would have allowed Lumpiston to win multiple championships instead of just the championship?
2. What if Anthony doesn’t sign a maximum of five years with the Nuggets?
While Darko Milicic has become a bust, the rest of the 2023 NBA Draft stars have become stars. By 2006, LeBron James, Carmelo Anthony, Dwyane Wade, and Chris Bosh were the top young stars in the league.
When it came time to sign their first stretches, James, Wade, and Bosh all signed shorter deals for less money that allowed them to become free agents in the summer of 2010. However, Anthony decided to sign the full five-year, $78,899,560 contract. The maximum extension, keeping him in Denver until at least the 2011 season.
All three of Anthony’s teammates successfully obtained free agency at the same time and joined the Miami Heat together, creating one of the greatest NBA teams in history. The trio of James, Wade, and Bosh would go on to reach four consecutive NBA Finals and win two championships.
Meanwhile, Anthony and the Nuggets were knocked out in the first round of the 2010 Western Conference playoffs, and by the next season, he was unhappy and eventually forced a trade.
What if Carmelo signs a shorter deal like James, Wade and Bosh? Would he have ended up in heat instead of one of them? Was he going to team up with one of them to take on the other two?
3. What if Anthony had waited to sign with the New York Knicks instead of forcing a trade?

In the 2010-11 season, with his classmates in the class of 2003 now living the high life in South Beach, Carmelo Anthony became unhappy in Denver.
There was a clear mutual interest between Anthony and Nicks. And in the final year of a contract extension, and his refusal to sign a new deal, Anthony had a lot of sway over the team that drafted him.
The then five-time All-Star pushed for a deal at the deadline, even though he could have just signed with the Knicks in free agency a few months later. Reckless Knicks owner James Dolan also wanted a trade, and a deal was struck in February 2012.
The blockbuster deal, which also included the Minnesota Timberwolves, looked like this:
- Knicks got: Carmelo Anthony, Chauncey Billups, Shelden Williams, Anthony Carter, Rinaldo Blackman (from DEN), and Corey Brewer (from MIN)
- Nuggets got: Wilson Chandler, Raymond Felton, Danilo Gallinari, Timofey Mozgov, 2014 Knicks first-round draft pick, 2012 and 2013 Golden State Warriors draft picks, $3 million, 2016 swap with (from New York), Costa Kovacs (from MIN)
- Timberwolves got: Anthony Randolph, Eddie Curry, cash (from NYC), 2015 second-round pick (from DEN)
This trade eliminated the Knicks from promising young players in Chandler, Felton, Gallinari, and Mozgov. Those chosen were Dario Sarek, Quincy Miller, Romero Ospi and, in 2016, Jamal Murray.
After the trade, Billups and Knicks star Amari Stoudemire was constantly injured. The Nuggets haven’t won much without a franchise star, but they’ve made the playoffs almost every year.
In the end, Melo made the playoffs three times with the Knicks, winning one playoff series.
But what would happen to Anthony in the 2010-11 season, sign him with the Knicks in the offseason, and have young teammates like Chandler, Felton, Gallinari, and Mozgov instead of aging teammates like Billups and Stoudemire?
4. What if Anthony retired after disastrous stints with the Oklahoma City Thunder and Houston Rockets?
Near the end of Knicks Carmelo Anthony’s tenure, the star clashed with team president Phil Jackson. This eventually led to a trade to the Oklahoma City Thunder. After one season with OKC, the Thunder traded Anthony to the Atlanta Hawks, who promptly bought him.
Then Melo signed a one-year deal with the Houston Rockets, and things didn’t go well there either. He played just 10 games for the team in the 2018-19 season before the team shipped him to the Chicago Bulls, who promptly waived the veteran.
What if Anthony had retired at that point?
This question is more answerable than any other. If Carmelo calls it a career in 2019, his legacy will be a star who failed to land the big role and couldn’t adapt to a lesser role, just like the player Anthony played with at the start of his career, Allen Iverson.
However, Anthony decided to return and became a valuable bench scorer and three-point cornerback specialist for two seasons with the Portland Trail Blazers. This role – along with a similar one in the 2021-22 Los Angeles Lakers – has diminished Carmelo’s reputation as an order of magnitude first shooter.
He also allowed him to score another 2,738 regular season points placing him ninth all-time in regular season NBA points with 28,289 and another 150 career playoff points, giving him a total of 30,203 points, which is 12th in league history. .
The comebacks of the past few seasons have also helped cement Carmelo Anthony as a confirmed Hall of Famer.