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Justise Winslow Is a Superior Fit With Trail Blazers Starters

Have the Blazers incorrectly chosen ability over fit in their starting small forward decision?

Portland Trail Blazers v Memphis Grizzlies Photo by Justin Ford/Getty Images

This week Josh Hart was named the Portland Trail Blazers’ starting small forward for the beginning of the team’s 2022-23 campaign, which opens in Sacramento on Wednesday night. While most Blazers fans probably weren’t particularly surprised by the decision, some were left wondering about the other two contenders for the role — Justise Winslow and Nassir Little.

The Blazers currently have Damian Lillard, Anfernee Simons, Jerami Grant and Jusuf Nurkic permanently penned in as starters this season. Lillard, because “duh”, Simons got paid after shining during the former’s absence last season, Grant was Portland’s big trade get of the offseason and Nurkic because ... there’s no one else.

The small forward position has been coined by many across the league as the most important in modern basketball. A role that straddles the need for handling, shooting and passing as well as defense, rebounding and paint play.

It’s why you see teams with the likes of Paul George, Kawhi Leonard, Jaylen Brown, Jayson Tatum, Jimmy Butler, Mikal Bridges, Khris Middleton and Andrew Wiggins dominate towards the end of the season and into playoffs. Kevin Durant and LeBron James became superstars in the league playing that position too.

The Blazers haven’t really had anyone shine at SF since Nicolas Batum was shipped off to the Charlotte Hornets in 2015. Since then it’s been Moe Harkless, Jake Layman, Norman Powell, Rodney Hood, Kent Bazemore, Trevor Ariza and Evan Turner rotating through the lineup.

Thanks to General Manager Joe Cronin’s trade deadline tear down of the team, the Blazers brought in Hart and Winslow, each with their own flaws but arguably well suited to the role. Not to mention Little, who has battled through injury, now finding himself in a contract year trying to prove his place in the league.

Interestingly, Gary Payton II was also brought in this summer using the mid-level exception. It’s clear the almost 30-year-old can comfortably play the three, but from what we’ve seen and heard, he appears to be an asset Coach Chauncey Billups is keen to use off the bench.

At Media Day, Billups told us that Hart, Winslow and Little would be vying for the last starting role and each would be given a chance to earn the spot.

Fast forward two weeks. Hart has started three of the five preseason games, Winslow one and Little the solitary win against a lesser opponent in Maccabi Ra’anana, when he played only 18 minutes.

And not surprising with the 22-year-old still working his way back from abdominal surgery. It has very quickly become clear that, at this point, Little wasn’t the trio’s frontrunner as he works his body and mind back into game shape.

But nothing is forever and many things for more than a week in the modern NBA. And as Little regains his game fitness, touch and rhythm, there’s nothing stopping him from leapfrogging Hart and Winslow with his youth, skillset, athleticism and energy during the season.

For the purposes of this piece we look at the merits of Hart and Winslow’s respective candidacies as starting small forward.

Why Josh Hart?

As I said, it’s not hard to see why Hart was chosen. Of the three players, he probably has the most ability at this point in time. He can expertly put the ball on the floor, sporting an innate instinct for slashing and finishing with consistency. Hart interestingly started his career with the Los Angeles Lakers as an elite shooter, hitting a shade under 40 percent of his threes through his rookie year. Unfortunately, his long-range numbers haven’t been as impressive since.

His assist numbers have, however, more than tripled, from 1.3 in 2017-18 to 4.3 last season. At 6’5, his rebounding is particularly notable, carrying a career 5.7 average and enjoying an astonishing 8.0 during the 2020-21 season. His 6’8 wingspan, basketball smarts and impressive lateral movement have also allowed the 27-year-old to guard positions one-through-three and in specific circumstances some power forwards.

It’d be hard to argue against Hart offering more than Winslow when it comes to putting the ball in the basket. You only need to look at his 2021-22 average (in both Portland and the New Orleans Pelicans) of 14.9 points on 34 percent three point shooting and 50 percent from the field.

At the end of last season Hart was told he would be more “guard dominant” this year, providing a scoring and facilitating burst off the bench. Great, but if he’s starting at the three, his production surely dilutes to sacrifice for those playing around him, namely Lillard, Simons and Grant. Conversely, a bench unit including Hart and one of Lillard and Simons, opens up a lot more doors for the versatile wing.

A starting Hart is probably a fourth, or even a fifth option on offense. Off the bench, he’s second and absolutely no lower than third.

And personally, I’d rather see him play shooting guard — but not in front of Anfernee Simons — using his speed and size to look down anyone playing the position and comfortably guarding opponents at the point of attack.

Why Justise Winslow?

I’ve been an unabashed Winslow fan for years and despite the injury setbacks, he’s consistently shown a unique ability for someone of his size and strength. When he was announced as one of Portland’s prizes in the much-maligned Los Angeles Clippers trade, I was pleasantly surprised.

Like Hart, Winslow is reliable with the ball in his hands, using solid court vision to pick out teammates and put them advantageous positions. But while Hart can indeed guard bigger wings in certain circumstances, Winslow is perfectly suited to the role thanks to his size.

Standing 6’6 and carrying more than 220lb, Winslow is both strong and nimble, able to stay with players at positions one-through-four. Last season, after arriving in Portland Winslow was tasked with guarding LeBron James in an unlikely Blazers win against the Lakers.

While James still had an impact on the game, the Blazers probably wouldn’t have prevailed without Winslow who registered four steals while keeping a positive plus/minus.

The 26-year-old is better equipped to guard those premier small forwards I mentioned earlier. The ones whose teams will be contending come May and June next year. And so, if Portland wants be competitive this season, it needs players who are able to quell impact players on the other side of the ball.

Carrying career numbers of 8.4 points on 31 percent three points shooting, it’s true that Winslow’s is not the offensive player Hart is, but this starting unit doesn’t need another Lillard or Simons.

Winslow also makes too much sense playing next to Jerami Grant. You could argue both players are 3.5s — Grant, who can play minutes at small forward and Winslow who can comfortably play the four. The pair offer a strong two-way forward duo, able to adapt to a range of matchups.

For a team that’s had to settle for undersized (Powell), one-dimensional (Harkless) options in recent years, why not engage someone that complements the players around him. The fit makes too much sense.


Hart, Winslow and Little are all in similar boats this year as expiring or potentially expiring contracts, which may also push the Blazers to move one or more at the deadline. Hart will confront a Player Option at the end of the season, which will see him paid $12.9 million for the 2023-24 season. But if he continues to contribute as he has over the past couple of years, it’d be very hard see him pick up that option, which means the Blazers would have to dig deeper into their pockets to retain him. At the end of the season, Winslow becomes an unrestricted free agent and Little will be restricted if he’s not extended this week.


Removing the convalescing Nassir Little from the conversation, there’s absolutely no doubt that Hart is the better player when compared to Winslow. But this team needs a starting small forward willing to do the dirty work and take on the tough defensive assignments, in many cases against some of the elite and big wings in the league.

Yes, Hart can score, but I just think his offensive talents can be used more effectively with the second unit. Winslow, on the other hand, has the size and demeanor to better support the starters while serving as an above average and versatile defender.

I might be slightly Winslow biased but I think he offers size, improved facilitating and hustle that will far enhance the skills of the players around him. I’m not upset with the decision to start Hart, I’m just wondering whether the team is better off going another way.