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On Monday, May 22, 2023, Carmelo Anthony announced his retirement from the NBA. The national championship-winning Syracuse star played 19 NBA seasons for six teams and scored 30,203 points, good for 12th-most in league history. Anthony had an excellent career, but he never won a championship in the pros, and his NBA journey is filled with “what ifs?”

There are four major “what if?” moments of Anthony’s career. If any of these situations turned out differently, they not only would have changed the star’s trajectory but the history of the NBA.

Here are these four burning Carmelo Anthony questions in chronological order.

1. What if the Detroit Pistons took Carmelo Anthony over Darko Milicic?

After winning a national championship as a freshman at Syracuse, Carmelo Anthony was the consensus No. 2 pick of the star-studded 2003 NBA Draft behind generational high school star LeBron James.

However, the Detroit Pistons won the No. 2 overall pick in the draft thanks to an ill-advised 1998 trade.   

That season, the then-Vancouver Grizzlies traded disgruntled veteran Otis Thorpe and a protected first-round pick to the Pistons for Bobby Hurley, Michael Smith, and Chris Robinson. Five years later, the pick still hadn’t transferred, and it was only protected for the No. 1 overall selection in the 2003 draft.

The Grizzlies — who had since moved to Memphis — actually jumped into the top three with just the sixth-best odds of getting the No. 1 slot. When the Grizzlies’ card came out at No. 2, though, the pick transferred to the Pistons.

Detroit was a veteran squad at the time, and they won the NBA title the following season. The team needed a big more than a small forward with Tayshaun Prince on the roster. And general manager Joe Dumars fell in love with Serbian teenager Darko Milicic after a chance run-in at John Jay College in Manhattan.

The Pistons took Milicic, Anthony fell to the Nuggets at No. 3, and the rest is history.

But while Milicic became an all-time NBA draft bust, what would Carmelo’s career have been like if he went to Detroit? Would Larry Brown have buried him on the bench like Darko? Or would he have become a valuable piece on a contender that would have allowed the Pistons to win multiple championships instead of just the one?

2. What if Anthony didn’t sign a five-year max extension with the Nuggets?

Carmelo Anthony with the Denver Nuggets in 2005.
Carmelo Anthony with the Denver Nuggets in 2005 | Jed Jacobsohn/Getty Images

While Darko Milicic became a bust, the rest of the 2023 NBA Draft top five became stars. By 2006, LeBron James, Carmelo Anthony, Dwyane Wade, and Chris Bosh were the top young superstars in the league.

When it came time to sign their first extensions, 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 Rookie Maximum Extension, keeping him in Denver until at least the 2011 offseason.

Anthony’s three fellow stars all hit 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-straight NBA Finals and win two championships.

Meanwhile, Anthony and the Nuggets went out in Round 1 of the 2010 Western Conference Playoffs, and by the next season, he was unhappy and ultimately forced a trade.   

What if Carmelo signed a shorter deal like James, Wade, and Bosh? Would he have ended up on the Heat instead of one of them? Would he have teamed up with one of them to take on the other two?

3. What if Anthony waited to sign with the New York Knicks instead of forcing a trade?

Carmelo Anthony with the New York Knicks in 2011.
Carmelo Anthony with the New York Knicks in 2011 | Christopher Pasatieri/Getty Images

In the 2010-11 season, with his Class of 2003 buddies now living the high life down in South Beach, Carmelo Anthony grew unhappy in Denver.

There was obvious mutual interest between Anthony and the Knicks. And in the final year of his contract extension, refusing to sign a new deal, Anthony had plenty of leverage over the team that drafted him.

The then-five-time All-Star pushed for a trade at the deadline, even though he could have just signed with the Knicks in free agency a few months later. Impetuous Knicks owner James Dolan wanted the trade as well, 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, Renaldo Balkman (from DEN), and Corey Brewer (from MIN)
  • Nuggets got: Wilson Chandler, Raymond Felton, Danilo Gallinari, Timofey Mozgov, the Knicks’ 2014 first-round draft pick, the Golden State Warriors’ 2012 and 2013 second-round picks, $3 million, a 2016 pick-swap with the (from NYK), and Kosta Koufas (from MIN)
  • Timberwolves got: Anthony Randolph, Eddy Curry, cash (from NYK), and a 2015 second-round pick (from DEN)

This trade gutted the Knicks of young, promising players in Chandler, Felton, Gallinari, and Mozgov. And those picks became Dario Saric, Quincy Miller, Romero Osby, and in 2016, Jamal Murray.

After the trade, Billups and Knicks star Amar’e Stoudemire were constantly hurt. The Nuggets didn’t win a lot without a franchise star but made the playoffs nearly every year.

In the end, ‘Melo made the playoffs three times with the Knicks, winning one playoff series.

But what would have happened in Anthony just played out the 2010-11 season, signed with the Knicks in the offseason, and had young running mates 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?

Toward the end of Carmelo Anthony’s Knicks tenure, the star clashed with team president Phil Jackson. This ultimately 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 out.

‘Melo then 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 retired at that point?

This question is more answerable than the others. If Carmelo called it a career in 2019, his legacy would have been of a superstar who failed to win the big one and couldn’t adjust to a lesser role, just like a player Anthony played with early in his career, Allen Iverson.

However, Anthony did decide to come back and became a valuable bench scorer and corner 3-point specialist for two seasons with the Portland Trail Blazers. This role — along with a similar role on the 2021-22 Los Angeles Lakers — diminished Carmelo’s reputation as a me-first, volume shooter.

It also allowed him to score 2,738 more regular season points to put him ninth all-time in regular season NBA points with 28,289 and 150 more playoff points, giving him 30,203 total points, the 12th-most in league history.

And coming back these last few seasons also helped solidify Carmelo Anthony as a surefire Hall of Famer.

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