NBA 5-on-5: Ben Simmons, Damian Lillard and the biggest remaining questions ahead of training camp

The peak of NBA free agency is in the rearview. The full 2021-22 season schedule has been released. Training camps can officially open on Sept 28. Still, there are a few potential moves that remain unresolved.

Will the Philadelphia 76ers trade Ben Simmons? How much longer will Damian Lillard remain with the Portland Trail Blazers? And which remaining free agents could make an impact on a contending team?

Our experts break down the biggest remaining questions and make their bold predictions as the offseason winds down.

MORE: NBA Power Rankings, post-free agency edition

1. How likely is Ben Simmons to start the season with the Sixers?

Royce Young: Conventional NBA wisdom says it's unlikely because media day and training camp set an unofficial deadline in these kinds of situations. The pending awkwardness of opening up camp with a player you intend to trade creates urgency, both for the Sixers and for the opposing teams that have been low-balling offers to this point. If Simmons isn't part of their future, moving on sooner than later has its own inherent value.

Nick Friedell: At this point, it's looking a little more likely by the day -- but it's still hard to believe that the Sixers would want to start the season with Simmons after the way things ended in the playoffs. Can you imagine how loud the "boos" will be the first time he messes something up or looks hesitant at the line? I understand not wanting to make a bad deal, but is it possible to fix his confidence when a portion of the fan base has already lost so much confidence in him?

Andrew Lopez: It seems very likely at this point, which is a bit of a surprise (to me, at least). There's still a chance that Daryl Morey tries to work a deal once training camp starts, but he's also going to try and get the most possible value for Simmons. That could mean a James Harden-type situation in which he plays a few games before a deal gets made. Still, it just feels like an awkward situation all around.

Kevin Pelton: My anticipation is that as training camp draws closer, the Sixers will face more pressure to trade Simmons. The question is whether that pressure will supersede the desire to hold on to their most tradeable player before the situations with Bradley Beal and Damian Lillard are resolved. I'm guessing that potential makes Simmons being part of the roster to start the season somewhat more likely than not.

Kirk Goldsberry: At this point, it's likely. The Sixers have been shopping him around for months now and have yet to find someone willing to give them the return they desire. The rumored packages Philly is seeking are massive, and it's unsurprising that they haven't found a trade partner willing to part with multiple picks and young talent in exchange for a player with some big questions right now. Simmons still has a chance to be a terrific two-way force in this league, but trading him now means selling low on him.

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2. How much longer will Damian Lillard be 'all-in' on the Blazers?

Goldsberry: Dame Time might be running out in Portland. Lillard wants to win, but there is a perception that Portland hasn't done enough to keep pace with the many Western Conference teams loaded with talent. The Trail Blazers don't feel like a legitimate contender, in part because their defense has been a mess for years now. Any team with Lillard and CJ McCollum will score well -- it's up to the front office to build a strong defensive group around them, and they just haven't been able to do it. As McCollum said, Lillard just wants to win a championship, and defense wins championships. If Portland plays great defense this year, Lillard could be content. If it doesn't, he won't be.

Lopez: Lillard had several chances to ask out this summer but instead turned that into trying to push Portland to upgrade its roster in hopes of getting the team closer to a title. And as McCollum said, Lillard does seem like he's all-in on this season. But whether he'll be all-in after this year is murkier. If Lillard feels like his championship window is closing -- and that the window won't be open in Portland -- maybe he makes a demand.

Friedell: Lillard has only ever talked about how much it would mean to him to stay in Portland, but he doesn't strike me as the type of guy who is going to have much more patience for losing. If the Blazers lose early and often this year, why would he want to stay? As a competitor, he has got to wonder what it's like to be on a team that competes for a title every year.

Young: At least until the end of next season. With Lillard, once the season starts, his focus centers entirely on the team, the staff and the organization. But when the season ends -- unless with a championship or a Finals run -- that forces reflection and evaluation, which is what happened this past offseason after a first-round exit. There will inevitably be some noise throughout the season, but Lillard won't be wandering. When the season starts, he's committed to his group.

Pelton: Only Lillard knows that, but I don't think Portland's coaching change and modest roster additions (signing Ben McLemore, Tony Snell and Cody Zeller to deals for the veterans minimum) will bring the Blazers appreciably closer to the championship goals Lillard has set. As a result, my expectation is that we'll see Lillard continue to express his displeasure with Portland's path after the upcoming season.

3. Which remaining free agent could provide the most help to a contender?

Lopez: The Dallas Mavericks pulling off a Lauri Markkanen deal would give their bench a big boost and give them a little bit of Kristaps Porzingis insurance in case the big man needs to rest. Markkanen had a career-high shooting season, hitting 58.2% from 2 (his previous best was 51.8%) and 40.2% from 3 (his previous best was 36.2%). Adding even more shooting around Luka Doncic can only be a good thing.

Goldsberry: I don't think any of them really move the needle with the possible exception of Paul Millsap. He might be able to slide into a reserve role and make a team like the Golden State Warriors a little bit more flexible or a little bit deeper, and that can go a long way in the postseason.

Young: Markkanen is an interesting potential piece for someone because of his combination of size and shooting ability. It's surprising he has been available this long, but defensive concerns and fit have apparently stalled his market. Markkanen is clearly the best player available and was productive with the Chicago Bulls, shooting 40.2% from 3 last season on almost six attempts. He's only 24 years old, with years of remaining upside.

Friedell: To me, Markkanen is the most interesting, but I'm not sure how much he'd help right away. The Bulls were hoping he would end up being a cornerstone for their future, but now he just looks like a young player who has lost a lot of confidence. He still has plenty of talent, but he has never been able to put it together consistently the way a lot of people around the league thought he would.

Pelton: Millsap. I'm surprised there apparently wasn't a market for Millsap at more than the veterans minimum this summer. While his minutes and 3-point percentage fell last season, Millsap remained an above-average contributor at age 36. I'd compare him to David West at the same age, when West signed with the Golden State Warriors and helped them to back-to-back championships.

NBA free agents: Team-by-team lists for 2022 and 2023

4. Which new coach has the biggest challenge this preseason?

Young: Jason Kidd. It seems as if Kidd was the handpicked successor to Rick Carlisle, but Kidd doesn't have nearly the same runway he's had before as he steps into his third head-coaching job. His hiring was controversial and not universally supported by the fanbase, and with the Mavericks already feeling the pressure of fielding a capable roster around Luka Doncic, Kidd will find himself in the crosshairs if Dallas gets off to a rocky start.

Lopez: New Orleans Pelicans coach Willie Green will have to fit three new starters around Zion Williamson and Brandon Ingram, as well as figure out what backcourt combinations are going to work. Jonas Valanciunas will get the nod to replace Steven Adams at center, but who replaces Lonzo Ball and Eric Bledsoe? The Pels added Devonte' Graham, Tomas Satoransky and Garrett Temple, and they re-signed Josh Hart to a backcourt that still has Nickeil Alexander-Walker and Kira Lewis Jr. Oh, and they drafted Trey Murphy III, who can play the 3, which would eliminate some three-guard lineup combos.

Goldsberry: Chauncey Billups. He inherits a team on the brink of major changes that is situated in a loaded Western Conference. If Lillard doesn't like the direction of the team, the situation in Portland could get uncomfortable fast.

Friedell: Willie Green. He has to make the Pelicans better -- while also trying to make Zion happy within the new system. Every coach has pressure in the league, but Green is coming into an organization that needs to win right away, while placating its young star. That's a tough task for any coach, but especially for a first-year coach trying to find the right balance with his new team.

Pelton: Going off my Lillard answer, I'd say Chauncey Billups in Portland. New boss Neil Olshey is on the record as saying last year's first-round loss was not a product of the roster. So expectations are high for Billups to take the Blazers deeper in the playoffs, despite more modest external evaluations of Portland's talent. The Blazers' opening over/under win total at Caesars Sports Book by William Hill (43.5) ranks eighth in the Western Conference.

Willie Green and Zion's bond impacts the Pelicans' fate

5. Bold predictions?

Friedell: I'm still banking on Lillard landing with coach Tom Thibodeau and the New York Knicks eventually. It might not happen for a while, but the marriage between Thibs and Lillard would be interesting to watch. So would the chance to see Lillard play at Madison Square Garden with a point guard he looked up to as he was entering the league -- Derrick Rose.

Young: It doesn't seem so bold to predict Simmons will be traded, but let's go with a surprise destination. Someone like the Blazers could be motivated to make a splash move, throwing assets and young talent at Philadelphia to try and boost the roster around Lillard. It's the kind of boom-or-bust move that could elevate the Blazers and ease the tension, or blow up in their faces and accelerate it.

Lopez: Millsap won't be on an NBA roster on opening night, but not because there's no interest. At 36 years old and with over 1,000 games under his belt, Millsap could opt to take his time in choosing a team and let it play out into the season, resting his legs just a bit longer.

Goldsberry: JJ Redick will end up on the Brooklyn Nets. It's just a hunch, but he loves New York, and a chance to reunite with some of his old LA Clippers buddies and compete for a title in a city he loves will compel him to join up with a team already loaded with other great shooters.

Pelton: The Oklahoma City Thunder will not trade for another first-round pick for the remainder of 2021.

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