Anfernee Simons to Hometown Orlando Magic Dream Fades to Black

Anfernee Simons’ long-awaited debut for the Orlando Magic will have to wait at least a few months and may indeed never come. Often linked as a trade target to land with the team he grew up rooting for, the 26-year-old guard was traded for the first time in his career by the Portland Trail Blazers late Monday, moving to the Boston Celtics for Jrue Holiday and a pair of second-round picks. 

Simons conceivably could be dealt again at some point this season since he’s on an always coveted expiring contract, but the 2023-24 NBA champs will see how he fits as they look to tread water without injured star Jayson Tatum. Plucked out of Florida’s IMG Academy by Portland in ‘19, Simons was mentored by Damian Lillard and CJ McCollum before emerging as the Blazers’ top guard the past few years. 

Magic fans have monitored his progress the way they would if he was a stashed European prospect. He may as well have been named Fran Vasquez.

Born in nearby Longwood and forever tied to Penny Hardaway, one of the Magic’s all-time greats, Simons rumors have grown quite popular in Central Florida. Even though the combo guard is a suspect defender and Orlando has built its identity on that side of the ball under head coach Jamahl Mosley, the team’s lack of scoring punch has made Simons a mythic figure of sorts. 

Land the hometown kid and he’ll never miss a shot. It was a Disney movie waiting to happen.

Simons did his part by proving he can be money late in games, coming through in the clutch on rare occasions where his Blazers had opportunities to actually win close contests. He’s averaged over 20 points over the past three seasons, starting 178 games, making over three 3-pointers a night and shooting over 90 percent from the free-throw line. 

The union wasn’t meant to be. Orlando opted for Desmond Bane as its top target and made him the first domino in what is looking like a busy NBA offseason, but what that also says is that dealing Anthony Black or Jonathan Isaac isn’t likely. 

Portland head coach Chauncey Billups landed a contract extension because he’s been able to turn the Blazers’ fortunes around by making opponents work for every basket. Wings Toumani Camara and Mathisse Thybulle are as tough as they come. Isaac and Black fit the roster profile of players Portland would love to land, so the fact it traded draft capital to move Simons for the 35-year-old Holiday to come in and mentor young backcourt pieces Shaedon Sharpe and Scoot Henderson probably means they were rebuffed in any talks with the Magic.

That should tell you how much Orlando values Black, the 21-year-old Texan who it took No. 6 just two Junes ago. Following a shaky rookie season, Black's versatility, defensive prowess and natural skill shined through in Year 2. The hope is he'll consistently develop his perimeter touch, but it's obvious how highly though of he is.

If Simons does ever suit up in Magic pinstripes, it’s going to have to be later in his career given Orlando’s salary cap situation and his own trajectory. He’ll have a great chance to improve his standing around the league in a contract year. Simons will enjoy the spotlight as Boston looks to build around Jaylen Brown and Derrick White while Tatum battles back from an Achilles tear expected to keep him out for most if not all of the season. 

Impressing on a Celtics team that thrives on 3-point shooting will take Simons out of Orlando’s price range next offseason given the salaries the Magic will be tied to going forward. It could also make him a key figure on a conference rival over the next few years. 

Simons’ trade to Boston solidifies that we’re unlikely to see Orlando make any more major moves this summer outside of handing All-Star Paolo Banchero his well-earned extension. 

One last tweak is coming, but unless they move bigs Wendell Carter Jr. or Goga Bitadze, it’s hard to see the Magic making another massive upgrade following the draft.

Moving on from veterans Gary Harris and Cory Joseph means it’s necessary to have another reliable guard on the roster since Jalen Suggs is working his way back from an injury. We’ll see what Jeff Weltman and the front office comes up with, but two things became obvious to begin draft week. 

Black is set to be a huge x-factor, and the Simons ship has sailed.