
Who might the Philadelphia 76ers tab to fill their two-way contract slots next season?
The Philadelphia 76ers don’t have any open roster spots — in fact, they actually need to trim down their roster between now and October. That doesn’t mean the importance of Summer League is reserved for those already on the roster, though.
With a pair of two-way contract spots now open, the Sixers will need to decide whose development is worth investing in. Jacob Pullen, Demetrius Jackson, James Young and James Michael McAdoo all held two-way spots at some point last season.
As things currently stand, the Sixers have likely focused their search on the Summer League roster. With that said, there is plenty of undrafted free agent talent available league-wide. Poaching someone from another team isn’t out of the picture.
That’s especially true with how deep this year’s class was. For example, Trevon Duval was considered the top point guard prospect coming into the 2017-18 season. After an inconsistent campaign at Duke, the talented guard went undrafted and is fighting for his NBA life on the Rockets’ summer squad.
Brett Brown has already done an excellent job traversing a difficult free agency market this offseason, with moves left to be made. The final piece to the Sixers’ proverbial roster puzzle, however, is the two-way contracts — and they have to chance to add some legitimately intriguing talent.

5. Chris McCullough
McCullough has spent three years in the NBA, split between the Brooklyn Nets and Washington Wizards. The former 29th overall pick has a real shot at the Sixers’ two-way spot based on pedigree alone. He’s a first-round talent whose athletic and skill profiles present lingering upside.
Health has been an issue for McCullough throughout his NBA career. As somebody who was considered a borderline lottery talent coming out of Syracuse, injury concerns pushed him to the end of the draft — where Brooklyn inevitably pulled the trigger.
His best season was his rookie season, averaging 4.7 points in just over 15 minutes per game. He only played in 24 contests, though, which is his highest mark for an individual season to date. The Sixers won’t invest in him unless they’re confident in his medical prognosis.
With that said, the talent has never been in question for McCullough. He’s a long, mobile center who can hit the occasional NBA three-pointer. His defensive prowess, when healthy, could give him a niche at the next level.
As Jonah Bolden struggles in Summer League and Richaun Holmes‘ future remains uncertain, investing a two-way contract in potential frontcourt depth makes sense. McCullough offers that while giving Brett Brown another first-round talent to insert into the Sixers’ player development system.

4. Duncan Robinson
Robinson is the only player on this list who isn’t currently affiliated with the Sixers. The former Michigan standout is playing with the Miami Heat this summer, and showing out in the process.
He never gained much traction as an NBA prospect, but Robinson has one very clear NBA skill: shooting. His quick, compact mechanics have made him one of the best individual shooters in Summer League, moving around screens and bombing with impressive efficiency from deep.
We’ve already had the full Furkan Korkmaz experience this summer, with the Sixers’ second-year wing going for 40 points in the first game and fizzing out in the second. With that in mind, it’s important that the Sixers continue investing in young shooters. Robinson fits the bill.
Landry Shamet has a real chance at getting minutes next season, but Robinson is another rookie who can gain valuable experience from playing behind J.J. Redick. The latter has embraced his leadership role with the Sixers, and Robinson is someone who can emulate him on the offensive end.
Robinson was a career 41.9 percent three-point shooter in college, filling a complimentary role similar to what he’ll play at the next level. His ability to work off the ball, stay in motion and knock down shots fits seamlessly in Brett Brown’s system.

3. Demetrius Jackson
Jackson spent part of last season with the Rockets before finishing the season as one of the Sixers’ two-way contracts. He only appeared in three games with the Sixers, playing garbage time minutes and averaging 2.7 points per game.
Familiarity is Jackson’s biggest advantage in this roster competition. He has been in the locker room and knows the system, something the Sixers, given their strong culture, certainly value. That could be enough to secure him another shot at cracking the roster next season, albeit space outside of two-way contracts is limited.
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With that said, Jackson probably isn’t the best option on this list. He might even be the worst. Despite many considering him a first-round talent coming out of Notre Dame in 2015, he simply hasn’t shown enough to warrant optimism thus far.
At 6-foot-1, Jackson is undersized and inefficient. He’s more of a volume scorer than a polished playmaker and lacks the consistency needed to provide sustainable production off the bench. He isn’t a great defender either.
His strong frame and plus athleticism leaves some upside, but Jackson simply hasn’t shown enough to earn another contract next season. Perhaps spending more time in the G-League, or trying his luck overseas, is the best developmental option.

2. Cameron Oliver
Outside of Korkmaz and Zhaire Smith, Oliver has been the best player on the Sixers’ Summer League roster. Oliver should have been drafted last season, but ended up without a team on draft night. Now he’s looking for his first legitimate contract heading into year two.
With a strong 6-foot-8 frame, Oliver projects as a small-ball five. He’s mobile for somebody with his bulk and can space the floor, traits that should improve his odds of sticking at the next level. He fits the modern NBA on both sides of the ball.
With Jackson, Smith and Korkmaz initiating most of the Summer Sixers’ offense, Oliver has thrived as a rim-runner. He makes hard cuts, fills the lane in transition and can finish above the rim with ease. If he were playing next to, say, Ben Simmons, he would only look better.
In two seasons at Nevada, Oliver was a 36.9 percent shooter from three-point range. If he were the inevitable replacement for Richaun Holmes, his ability to space the floor and defend at the rim would be immediate improvements. He, more than anyone else mentioned on this list, has a clear path toward carving out a role in the near future.
If Oliver doesn’t get a contract with the Sixers, he’ll almost certainly be signed elsewhere. His skill set, especially in the modern NBA, just isn’t something too many teams will pass on. He played with the Sixers’ G-League squad last season, meaning the organization already has some level of familiarity beyond Summer League.

1. Shake Milton
Despite receiving first-round grades from several draftniks, Milton ended up falling to the Sixers at 54 in the 2018 draft. The reason for his fall could be injury-related, as the former SMU guard suffered a stress fracture in his back during the pre-draft process.
Milton is a clear fit with the Sixers’ current roster — he can defend three positions, hit open shots and create in the pick-and-roll. He helps fix the Sixers’ lack of self-creation in the second unit and adds another versatile body to their defensive core. As a late second-round pick, he might be the steal of the draft.
The only issue is that the Sixers can’t give him a roster spot outright. As things currently stand, Jonah Bolden would give the Sixers 17 players under contract. There are ways to cut the roster down to 15, but it’s unlikely that Milton would be one of the 15 traditionally-rostered players.
That’s why the two-way contract is so valuable. The Sixers can retain his rights while allowing him to split time between the NBA and G-League. If Milton gets healthy and shows proper growth, then the Sixers can consider opening up a roster spot later in the season.
It’s rare to find ball-handlers who stand 6-foot-6 with a 7-foot-1 wingspan, even in the increasingly versatile modern NBA. Milton will need to improve his handles and become more reliable off the dribble, but his base skill set is impressive.
Next: 3 reasons the Sixers won the 2018 offseason
Expect him to be with the team in some capacity next season.

