Throughout the first five years of his pro career, Cole Anthony committed himself to the city of Orlando on and off the court.
In March 2024, he won the Magic’s Rich & Helen DeVos Community Enrichment Award for the first time, and last fall he was named the NBA Cares Bob Lanier Community Assist Award winner for October.
So it was only fitting Sunday when the former Magic guard, who was traded earlier this summer, and his 50 Ways Foundation held a back-to-school community event at the Smith Center that also served as a farewell to the local area.
“It was just important to let the community know that we’re still here,” Anthony said. “Orlando still means a lot to us. We still are thankful for how the city’s embraced us and everything. We wanted to do something for the kids because that’s what it’s really about — the next generation.”
In mid-June, the Magic sent Anthony, guard Kentavious Caldwell-Pope and four future first-round picks as part of a blockbuster trade with Memphis in exchange for Desmond Bane, who averaged 19.2 points, 6.1 rebounds, 5.3 assists and 1.16 steals per contest last season.
Anthony, who was drafted by Orlando 15th overall in 2020, couldn’t believe what happened when Magic president of basketball operations Jeff Weltman called him.
“I remember my agent called me; I remember talking with Jeff, and I was just like, ‘Dang, is this real?’” the 6-foot-2 guard said. “I remember that whole week; it was just crazy.
“I’ve been here five years, haven’t played for another team, was drafted here, so it’s something for me that definitely is bittersweet and I’m going to miss it.”
While Caldwell-Pope stuck with the Grizzlies, Anthony did not.
Instead, he signed with the Bucks in July after he agreed to a buyout with Memphis. Anthony, 25, will join former Magic guard Gary Harris, who also signed with Milwaukee as a free agent after Orlando declined his club option for the upcoming season.
Youth wearing Magic and Bucks gear asked Cole Anthony for his autograph Sunday at the Smith Center during a back-to-school event. Anthony recently signed with Milwaukee after a buyout with Memphis, who acquired him from Orlando. (Jason Beede/Orlando Sentinel)
Anthony and Harris will suit up alongside two-time NBA MVP Giannis Antetokounmpo, who led Milwaukee to its second league championship in 2021. Anthony wants to help Milwaukee get back to the top after three straight first-round postseason exits.
“I look at it as a great opportunity to enter another team where they have a playoff pedigree and a championship pedigree,” Anthony said about joining the Bucks. “They’ve won a ‘chip there. I just want to get in there, contribute and do whatever I can for the team. I want to be a part of winning.”
The full NBA schedule is expected to be released Thursday and Anthony will face his former Eastern Conference team at least three times in the regular season.
He anticipates mixed emotions when he returns to Kia Center.
“It’s definitely going to be really bittersweet,” Anthony said. “I’ve literally said this to several people … I still feel like I’m on the Magic a little bit.
“It’s something that’s bittersweet because this has been home, but I’m super excited for this next opportunity and super thankful to the whole Bucks organization.”
Jason Beede can be reached at jbeede@orlandosentinel.com
Originally Published: August 10, 2025 at 2:15 PM EDT