NBA Season Preview 2019-20: The 5 biggest questions for the Portland Trail Blazers

The Portland Trail Blazers are pushing for a championship, keeping all their chips in the middle of the table. How will it work out this time?

The Portland Trail Blazers had a mostly successful season last year, finishing third in the Western Conference with a 53-29 record. Lead by their franchise guards Damian Lillard and CJ McCollum, they were able to knock off the Oklahoma City Thunder and Denver Nuggets on their way to the Conference Finals where they were defeated by the Golden State Warriors in four games.

The Trail Blazers made big moves in the offseason, in another attempt to craft a roster that can deliver a trip to the NBA Finals with Lillard at the helm. Neil Oshey used the 25th overall pick in the NBA Draft to select University of North Carolina forward Nassir Little, adding wing depth to a team that didn’t receive the production they needed from Mo Harkless and Al-Farouq Aminu. Four days after the draft, Oshey made a horizontal move, swapping Evan Turner for Kent Bazemore in a trade with the Atlanta Hawks. Once the free agency market was open, Oshey set out to add more wings to his team, signing Anthony Tolliver, Mario Hezonja, and re-signing postseason hero Rodney Hood.

The final big move for the team came as part of a four-team trade, where Portland sent Meyers Leonard to the Miami Heat, Harkless to the Los Angeles Clippers, and received Hassan Whiteside from Miami in exchange. Whiteside put up huge stats for the Heat over the past few seasons and offers the potential to be an excellent injury replacement for Jusuf Nurkic, who suffered a severe leg injury in March and will miss time to start the season. They capped things off by signing veteran big man Pau Gasol at the end of July, but the former NBA champion likely won’t be much more than a third-string center.

This year’s roster will look much different than previous seasons. Gone are Aminu and Harkless, creating openings in the starting lineup for new faces. Former reserve Zach Collins is penciled in as the starting power forward alongside Whiteside, giving the team a jumbo frontcourt in an era where more and more teams are putting smaller players with more perimeter skills at that position. While Aminu and Harkless brought size and speed to the wing, they’ll try to replicate that with Rodney Hood or Kent Bazemore at small forward, helping to stretch the floor for Whiteside, McCollum, and Lillard.

Let’s get to some of the big questions this team has as the season tips off.

1. Is there any scenario but a Finals appearance that the Blazers can consider a success this season?

As long as Damian Lillard is at the helm of this team, an appearance in the NBA Finals has to be the goal, and anything else has to be considered a failure. He’s one of the best players in the league, one of the best leaders in the league, and has the ability to win games on his own. Neil Oshey has been in charge of the team for the entire decade, and they’ve reached the Conference Finals one time.

The time is now for Portland to make a Finals run. The Warriors will be without Klay Thompson for most of the season, and even after his return, have questionable depth. The Nuggets have already proven to be a team the Trail Blazers could beat in a seven-game series. The Lakers made some pretty obvious changes but could be derailed by injuries that expose their lack of depth and shooting. The Rockets are a viable contender, but Portland has experience defeating teams that rely on Russell Westbrook. The Clippers added Kawhi Leonard and Paul George, but recent history might say that the Trail Blazers could beat them too.

There’s no time like the present. If their new pieces fit well, they have the talent to make it to the Finals. They’re going to need a reliable third scoring option to find success in the playoffs, which makes Nurkic’s return to full health of vital importance for their playoff hopes.

2. Will Hassan Whiteside’s season be: lol or btb?

Whiteside and Lillard supposedly have a relationship off the court that the players think will result in success on the court. Based on prior levels of performance, however, it’s more likely that Whiteside’s season will be more LOL. He’s not going to magically become a better passer, and he doesn’t have range outside of the paint. He could be really exposed at times in the Western Conference, but Portland has other options they can turn to if Whiteside struggles.

If he is going to succeed, the team is going to have to adapt their defensive strategy to take advantage of his ability to be tall and have long arms while standing near the rim. Unfortunately, that’s not going to work against centers like Karl-Anthony Towns or Nikola Jokic, who are on division rivals. It could be a rough year for the residents of Whiteside Island.

3. Are you buying or selling stock in Rodney Hood as a reliable third scoring threat?

Hood played about as well as he possibly could have played in Game 6 of the Conference Semifinals last season, torching Jamal Murray and the Denver Nuggets for 25 points on 12 shots. He was able to use his size to post up his smaller defenders, turn and shoot over the top. If that jump shot is going to fall consistently, there’s no reason to not go to it more often this season. His problem continues to be that he struggles to drive to the rim and get to the free-throw line. He’s not much of a threat from behind the 3-point line, and without those free throws, if his mid-range jumper is off or he gets fatigued late in the game, he’s not going to be helpful.

4. Who makes a more meaningful contribution this season — Nassir Little or Anfernee Simons

Anfernee Simons is the pick here. Simons was able to learn the Trail Blazers system last season, and can step into the role that Seth Curry filled last season. Simons has shown flashes of good athleticism, an ability to defend well, and he can get to the rim. The Trail Blazers are going to need someone to not only help lead second units but to allow Lillard to play some minutes off-ball. He’s going to need to take care of the basketball, rebound, and not get lost on defense in order for Terry Stotts to feel correct in his decision to keep him out on the court.

Nassir Little is playing behind several other players who have much more experience than he does. He might be well-served by taking off most of the year to learn from his teammates as they try to make another playoff run.

5. Using Popeye’s Spicy Chicken sandwiches as a unit of measurement, how big a leap does Zach Collins take this season?

Does anyone know someone that actually had one of these sandwiches? Did you yourself eat one? Were they any good? I’m highly skeptical of these mythical sandwiches, just like I’m skeptical of Zach Collins taking a leap. He’s going to need to channel his aggressive style of play into something where he doesn’t foul as often.

Collins has the athleticism to be a force on both ends of the court, but too often, it looks like he’s not sure what to do. If he can add more polish, and play with more wisdom, I could see him making a two Popeye’s Spicy Chicken sandwich level type of jump.