Kemba? Kawhi? Kyrie? Here are major offseason questions in NBA Eastern Conference

CHICAGO BULLS: Is the future bright enough to land some decent free agents this summer?

With the addition of Coby White to a young core of Lauri Markkanen, Wendell Carter Jr., Zach LaVine and Otto Porter, the Bulls are starting to look like a team that could compete for the playoffs sooner rather than later. Will that promise, combined with the approximate $18 million in cap space, help them get any free agents without having to severely overpay? Could this be a surprise landing spot for a nice two-way player like Malcolm Brogdon or Willie Cauley-Stein? Would a veteran like Thad Young come be a mentor for some of the younger players as they begin to be competitive in the Eastern Conference?

CLEVELAND CAVALIERS: Does anyone on this roster know how to pass?

Seriously, let’s take a look at the top ball handlers on this roster as currently constructed. Collin Sexton averaged three assists in 32 minutes per game last season. Darius Garland averaged three assists per game in the five games he played at Vanderbilt. Jordan Clarkson? He averaged less than a pass per minute last season and nearly nine passes per game less than Tristan Thompson!! The Cavs desperately need a veteran point guard to help distribute touches on this team -– and, no, Matthew Dellavedova doesn’t count.

DETROIT PISTONS: Will they take an “L” on an Andre Drummond or Reggie Jackson trade to accelerate a rebuild? 

Drummond’s gaudy numbers (17 points, 16 rebounds and two blocks and steals per game) don’t really match his trade value. With the NBA moving toward the perimeter, Drummond is a rebounding dinosaur. Trading him and his max contract would certainly help the Pistons accelerate a rebuild around Blake Griffin. But Detroit’s yield wouldn’t come close to matching what a team typically gets for a 25-year-old on a max contract. The Jackson situation is even more gloom as the Pistons would likely have to attach an asset to him to get out of his contract. It might be worth bringing the core group back from last season, competing for the No. 7 or No. 8 seed again, and then working with a cleaner cap sheet next summer when Jackson comes off the books.

INDIANA PACERS: Can they pay Bojan Bogdanovic what he’ll get offered on the open market?

With Victor Oladipo expected to be sidelined for the first half of the season, the Pacers will have the same struggles they had in the playoffs this past spring: scoring. Unrestricted free agent Bogdanovic, who averaged 18 points on 50-42-81 shooting last season, was the closest thing the team had a go-to shot creator. He’s expected to draw plenty of interest on the open market, especially from the Spurs, according to ESPN’s Bobby Marks. Does the team’s acquisition of TJ Warren last week signify that the Pacers don’t believe they’ll have the money to keep Bogdanovic?

MIAMI HEAT: Are the Heat just the Hornets with better branding?

Speaking of salary cap hell, the Heat would have to move approximately $45 million to even be close to having enough money to offer a free agent the standard mid-level exception (expected to be in the $9.2M range). Thus, unless Pat Riley has some grand plan that involves dumping the atrocious contracts of Hassan Whiteside, James Johnson and Ryan Anderson, then this Miami roster has little to no upside this off-season. Miami must hope Josh Richardson, Bam Adebayo, or Justise Winslow take quantum leaps from intriguing young role players to bonafide stars. The Heat's best move might be to try to swap one of the aforementioned contracts and a draft pick or two for a bad contract with a little upside (T-Wolves Andrew Wiggins?). If anyone could get the most out of Wiggins, especially on defense, it’s Eric Spoelstra.

MILWAUKEE BUCKS: Which of their own free agents – Khris Middleton, Malcolm Brogdon and Brook Lopez – do they lose this summer?

Even though they were able to trade Tony Snell’s contract to the Pistons, the Bucks will almost certainly be unable to retain all three of the above players. In fact, even if they’re able to unload Ersan Ilyasova’s contract, they still can probably only keep two of the three because Middleton will command the max or close to it, and Brogdon and Lopez are desirable free agents for contenders. If they can retain Middleton and Brogdon, that should be enough to keep the team in title contention next season. The Bucks’ goal should be to do whatever is necessary to please Giannis Antetokounmpo, whose first major free agency comes in the summer of 2021.

NEW YORK KNICKS: Can they lure Kevin Durant to the Big Apple? 

For an off-season that began with so much promise -– remember not that long ago when New Yorkers thought they might get KD, Kyrie and either Anthony Davis or Zion Williamson? -– there’s a solid chance  the Knicks enter next season with RJ Barrett and a couple of B- or C-level free agents. Or the Knicks could land Durant and use this next season to build or prepare to build a roster around him for the start of the 2020-2021 season. It’s a pretty wide variance –- the latter would still be a success based on Durant’s name brand alone. The latter would also allow for the most growth from Barrett.

ORLANDO MAGIC: Has Markelle Fultz remembered how to shoot yet or will the team sign a point guard?

The Magic surprised people when they selected a forward recovering from an ACL tear with the No. 16 pick in the draft (Chuma Okeke) over ball handlers Nickeil Alexander-Walker, Ty Jerome and Kevin Porter Jr. This would seem to indicate that the Magic are content with what they have on their roster (D.J. Augustin, Markelle Fultz and Evan Fournier) or they have a point guard targeted in free agency. There are no reports of Fultz getting over his curious case of the yips, so that would seem to indicate that Orlando might have its eyes on a couple mid-tier point guards (Terry Rozier or Ricky Rubio) this summer. The good news is that Steve Clifford already has experience fixing a top-two draft pick’s broken jump shot from his days in Charlotte (Michael Kidd-Gilchrist) ... oh, never mind.

PHILADELPHIA 76ERS: Can they retain Jimmy Butler, Tobias Harris and JJ Redick?

The short answer is probably “no,” unless all three take pay cuts. The next question: How do the Sixers prioritize these three pivotal players? The consensus is that the team will definitely offer Butler the max or super-max extension and likely offer Harris the max as well. While losing Butler or Harris would certainly be an egg on GM Elton Brand’s face, he may want to consider making Redick his second priority due to his excellent dribble hand-off chemistry with Joel Embiid and ability to space the floor around Embiid and Ben Simmons. Harris is a nice talent square in his prime, but he probably doesn’t have the same impact on winning for Philly as Redick does.

TORONTO RAPTORS: Do you really need to ask? 

Have they done enough to convince Kawhi Leonard to re-sign with the team? If that answer is a “yes,” Toronto will have a legitimate chance to defend its title in 2020. If that answer is a “no,” then there was never anything the franchise could have done to keep Kawhi as it exhausted every resource in appeasing the two-time Finals MVP. If it loses Kawhi, the focus should immediately shift to keeping Masai Ujiri, the architect behind Canada’s first championship roster in the NBA.

WASHINGTON WIZARDS: Will the Wizards land their biggest free agent target – Masai Ujiri?

The Wizards are without a head executive or a plan. Their lack of a team president/general manager was on full display during the NBA Draft as they selected Gonzaga’s Rui Hachimura with the No. 9 overall pick – a low-value pick with major defensive flaws according to most NBA analysts. This summer, since the Wizards can forget about signing any major free agents (they have neither the cap room nor the allure), they should up their reported offer to the NBA’s best roster architect, Masai Ujiri. Offer Ujiri $12M-$15M and equity in the team (they’ve reportedly offered him $10M, plus equity), because if you’re going to pay Ian Mahinmi over $15M this year, you might as well pay a smart team builder so that you avoid handing out such a despicable contract in the future.