Enrique Freeman does not look locked into a two-way contract with the Minnesota Timberwolves.
Right now, Minnesota’s three players on two-way deals are Zyon Pullin, Rocco Zikarsky and Freeman. Zikarsky and Freeman spent all of last season in those spots, while Pullin signed his two-way contract in March after playing for the Iowa Wolves.
Nothing has to stay the same when the regular season arrives. Because waiving a two-way player does not affect a team’s salary cap, the Timberwolves still have room to make changes. And based on what’s happened so far, Freeman’s hold on one of those spots looks shaky.
Antonio Reeves and Norchad Omier have both spent time on training camp deals, and both have played a little more than Freeman while also looking more effective in their minutes.
Freeman has not made a strong case in limited NBA action. He appeared in only four games for Minnesota last season, and in 22 games with the Indiana Pacers in 2024-25, he still didn’t show enough to feel like a clear-cut NBA rotation player. The 6-foot-9 forward also turns 26 on July 29, so he is not exactly the kind of developmental flyer teams often stash and wait on.
His preseason has not changed that picture. Freeman did not play in Minnesota’s latest exhibition against the New York Knicks on Monday, and across his three preseason appearances he has logged just 16 minutes and shot 1-for-6 from the floor.
He has put up plenty of 3s in the G League, but he has not hit enough of them to be treated as a real outside threat. And while he was a standout rebounder at Akron, that strength has not really carried over to the NBA level yet. Freeman, a 50th overall pick in the 2024 NBA Draft, has only 218 career minutes, so the sample is tiny - but the early returns still matter.
If Minnesota is deciding between keeping a familiar face and choosing the player with the more obvious NBA skill, Reeves may have the edge. He is not much younger than Freeman, turning 26 on November 20, but he brings something much easier to spot: 3-point shooting.
In 54 NBA games with the New Orleans Pelicans and Charlotte Hornets over the last two seasons, Reeves has knocked down 58 of 142 attempts from deep, a 40.8 percent clip. He also shot 44.7 percent from 3-point range in his final college season at Kentucky.
He backed that up last Saturday with a game-winner, sinking a floater with 2.3 seconds left against the Miami Heat. In the preseason, Reeves has gone 3-for-5 from long distance.
Minnesota could still lean on continuity and keep Freeman. But if the Timberwolves are choosing based on upside and a player who already has a clear NBA skill, Reeves looks like the stronger candidate for that two-way spot.
In Other News...
Joan Beringer Is Giving The Wolves One Big Reason To Worry
Joan Beringer has given the Timberwolves a useful preseason glimpse of what he might become, and the early returns are hard to ignore. In limited minutes, he has flashed real value around the basket, averaging 7.3 points, 6.5 rebounds and 1.8 blocks while giving Minnesota the kind of interior activity teams can lean on when the game gets physical.
The concern, though, is just as clear. Beringer is also averaging three fouls in about 17.6 minutes, and for a team that may need him more as Rudy Gobert gets older and potentially gets managed more carefully, that kind of whistle trouble can become a real issue. Minnesota does not have much room to spare in the frontcourt, so how quickly Beringer learns to defend without sending people to the line could shape how much trust he earns early on. [Read more 🡒]
Former Bulls Guard Now Faces A Brutal Question About His NBA Future
Rob Dillinghams path from highly regarded draft prospect to uneasy NBA afterthought has moved faster than anyone in Minnesota likely expected when the Timberwolves took him eighth overall in the 2024 draft. A standout at Kentucky, Dillingham arrived with real intrigue as a guard who could score and create, but the transition to the league has been rocky, with his size and defensive limitations making it difficult for him to carve out a stable role.
Now without an NBA contract after being traded twice and waived by three teams, Dillingham has become part of a larger leaguewide conversation about young guards who look better on the draft board than they do once the games count. NBA draft analyst Rafael Barlowe and other scouts have started revisiting whether the initial evaluation oversold his upside, or whether teams today simply have less patience for players who need time to develop, leaving Dillingham facing a much harsher question than he did on draft night. [Read more 🡒]
Tim Connellys Latest Wolves Swing Just Changed The Pressure On Everyone
Tim Connelly has made a habit of keeping the Timberwolves in motion since taking over as president of basketball operations in 2022, and this latest move fits the pattern. After a stretch that included headline-grabbing deals for Rudy Gobert and LaMelo Ball, Minnesota has continued to chase the kind of top-end talent it believes can keep the roster in the Wests upper tier. The Wolves made the Western Conference finals in 2024 and 2025, so the pressure around every Connelly swing has only grown louder.
The latest pivot came after Minnesota fell in the second round in 2026, pushing Connelly to rework the core again by moving Julius Randle and Naz Reid for Ball. With Jaden McDaniels drawing encouraging preseason attention, there is at least some reason to believe the framework around the new-look group can still hold up. Still, the bigger question now is whether this kind of constant reshuffling has finally raised the stakes for everyone in the organization, from the front office down to the players expected to make it work. [Read more 🡒]