Does Winning Matter?

Let me explain!

Recently, I was listening to a Raptors podcast called Runnin’ off the Screen— a great listen, by the way— and host Mac Cunningham was discussing the new era of the Toronto Raptors; a post-Siakam, post-Anunoby, rebuilding era that will intentionally include plenty of losing. (It already has, actually; Toronto is 7-16 since the Anunoby trade.)

He brought up a point that stuck in my brain, asking how Toronto can surround young All-Star Scottie Barnes with a team that’s able to win and develop simultaneously. I have no answer for that in Toronto’s case, specifically, but his question made me think about rebuilding in the general NBA, eventually leading me to ponder just how important a team’s record is when trying to develop players.

NBA folks believe that when a team is full of young players, development is paramount; the record of the team is almost meaningless. I’ve always subscribed to that idea too, but if we look around the NBA right now, very few current contenders with homegrown stars operated with that mindset. There are a few exceptions to every rule (Oklahoma City, I’m looking at you) but the landscape of the NBA in 2024 might prove that trying to win in conjunction with a young star’s development is a more effective path to success— both individual and team—than trying to develop him in spite of team success.

Denver didn’t make the playoffs until Nikola Jokic’s fourth season but it was never woeful in those first three, winning 33, 40, 46 games, respectively. It never tanked while Jokic was on the team, never prioritized the hypothetical— draft picks, cap space— over the tangible.

Milwaukee was abysmal during Giannis Antetokounmpo’s rookie year (15-67) but has reached the playoffs (at least) in eight of his nine other seasons. And once Giannis showed real promise as a franchise cornerstone in 2016, Milwaukee never looked back, striving for success every season.

Philadelphia had to be atrocious for a few years in order to get Joel Embiid, but have only attempted to win since he finally took the court in 2016-17 after missing two full seasons.

Memphis (who certainly isn’t a contender this year but should be back in the fold in 2024-25) has always tried to build around Ja Morant— the Marcus Smart trade will work out eventually, I’m confident in that.

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This quandary isn’t that straightforward though. It’s tricky, in large part because of how fluid team building can be. For example, what’s the most recent instance of a team—whose best players are still getting better— advancing past the second round of the playoffs?

You don’t have to strain your brain too hard because it happened five years ago with the 2019-20 Boston Celtics, when Jayson Tatum was in just his third season and Jaylen Brown was in his fourth. Of course, that team wouldn’t have made the run it did without veteran contributions from Kemba Walker, Gordon Hayward, and Marcus Smart, but its two leading scorers were both young players who—as we now know—still had room to grow into stars.

Is that Celtics team a viable blueprint for other teams to follow?

Well, one team is already trying to do it, and early returns are positive; the Minnesota Timberwolves are prioritizing Anthony Edwards’ development (and he is developing rapidly) by surrounding him with talented veterans. Essentially, the Wolves are saying “if we win now, great. If we don’t win now, at the very least we’ll still have a superstar who became a superstar in part because we tried to win while he was still growing.”

But here’s the thing: outside of Boston, young teams that are led by improving stars don’t make deep playoff runs often, and this might be the precipice on which the validity of the when you have a good young player, try to win argument hinges. Because now we must determine whether making the playoffs and potentially winning one series is a positive enough outcome to feel confident about surrounding your young star with talent at the expense of future draft capital and cap flexibility. In other words, is being a middling team with a great young player and limited draft/cap space better than being a bad team with a great young player and many more resources for team building?

Frankly, I still think so. Like I said— building your team through hypotheticals, through ideas of what could happen or how great a draft pick could be at the expense of what’s happening in front of your eyes— is a dangerous way to live.

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Currently, the two best players on abysmal teams are— pretty comfortably— Cade Cunningham and Victor Wembanyama. Both number one draft picks, both undoubtedly still learning the NBA game, both posting big numbers on teams with some historically dreadful stats.

Now let’s look at the opposite end of the spectrum; in his second season, Jalen Williams is the third-best player on one of the West’s best teams. Is Jalen Williams a better player than Cade Cunningham? Or has Williams been privileged to develop on a very good team while Cunningham toils away in Detroit? Would Cunningham be able to produce similarly to Williams if they traded places? I don’t think it’s an outlandish thought.

I can picture Cade Cunningham contributing greatly to a winning team one day, but I have a hard time picturing that team being Detroit. That might be why I’d still rather be a mediocre team with a great young talent than a team that’s fully bottoming out with one. Because while Cunningham’s development as a player isn’t necessarily stunted, his development as a Piston likely is. It’s really, really hard to develop a player when the franchise around him doesn’t care about wins and losses at all. It can be done, but very rarely does that player find his success on that same team.

Devin Booker might be the only current exception to this rule— he survived the dumpster fire that was the Phoenix Suns franchise in the mid 2010s, and came out a star anyway. Victor Wembanyama will most likely be an exception to this rule, too, but he’s an exception to every rule.

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I don’t think Nikola Jokic and Jayson Tatum would be lesser players if they developed on teams that lost a bunch, but I also don’t think it a coincidence that the two Finals favorites—and most other elite teams today— are led by players who didn’t develop on teams that lost a lot.

Don’t prioritize hypotheticals. If an NBA team has a player on its roster that it believes is a star, it’s close to a responsibility of that team to build the best roster around that player as quickly as possible. Because whether or not you win quickly, “restarting” with a star who grew as you tried to win is a much better place to start building from than with a star that’s only been a star player on bad teams. Of course, that player still could be a star, but at that point you’re taking a risk; you’re hoping he turns into a star, when giving him the best tools to become a star was an option all along.

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What I’m Listening to: Tim Hecker

This is the last song that made me cry, if you’re wondering.

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