DeMarriage with DeRozan and DaBulls

How these two live happily ever after

Sometimes, the biggest gamble is the one you don’t take. 

That is the credo which I have lived my life by, and I’ve been thinking about it as I evaluate the Bulls trading heaven and earth to give DeMar DeRozan a massive $85 million contract over the next three years. There’s no getting around the fact that the price was steep. Will it be worth it? 

There’s a parallel universe out there where the Bulls passed on DeRozan. Instead, they kept Thad Young, their 2025 first round pick, two seconds, and added a couple of back-end rotation pieces to roll into next season. That was the safe and prudent route, one where Arturas Karnisovas would be free of criticism and praised for a solid offseason. But Karnisovas didn’t grind for 17 years in basketball jobs for the opportunity to play it safe. On some level you have to respect that. If he’s going to fail, it’s going to be on his terms. 

The DeRozan signing is a massive gamble, but there is also a lot of upside. He was the best option still out there for the Bulls to shore up their most glaring need at wing. He’s still a great offensive player. Known as somewhat of a chucker earlier in his career, he’s remade his game to become more efficient. He still rarely shoots 3’s, but he is so crafty in the midrange with his variety of step-throughs and fakes that he can score efficiently and get to the line a ton. 

DeRozan has also become an excellent passer. The Bulls needed some extra playmaking juice in their halfcourt offense, and he was one of the best creators out of pick-and-rolls last year. He is going to feast on pick-and-pops with Nikola Vucevic.

DeRozan isn’t the type of player that you can just drop into a lineup. Billy Donovan will have to figure out a way to fit him in, but it can work by mostly putting the ball in his hands. The Spurs used him a lot as a quasi point-forward, and the Bulls will have to mimic that plan to get the most out of him. 

Another plus is that DeRozan needs a lot of spacing to maximize his game, and he will have way more shooting around him than he did with the Spurs or Raptors.

Defense is an obvious issue for these new-look Bulls. Zach LaVine is not nearly as bad as his reputation (here’s my deep dive of his defense), but I would still rate him as a little below-average. Vucevic also does not get enough credit for things that he does well defensively (here are two great examples (1) (2)). Admittedly, he doesn’t have as much scheme versatility as other bigs in the league, but he can hold his own in the regular season when teams don’t gameplan as diligently to beat him. DeRozan presents a whole other challenge. 

DeRozan is a lot worse defensively than his reputation, and why I initially had mixed feelings about the signing. I’m not going to sugarcoat it -- He is among the worst defenders at his position in the league. He has a combination of poor technique, awareness, effort, and he complains way too much about foul calls rather than getting back on defense (a particularly big pet peeve of mine). 

Here are my best arguments for why DeRozan’s defensive woes might not matter:

  1. The Bulls built a pretty solid defense last year with a worse defender than him, Coby White, in the starting lineup. There was a lot of hand-wringing about how bad the Bulls’ defense was going to be with the LaVine-White duo, yet they finished tied for a very respectable 11th-best defense overall. They were also ranked 11th after the trade for Vucevic, which is somewhat amazing given that they remade a huge chunk of their roster and had only one real practice with that new group all season. 

  2. On that note, Billy Donovan is an underrated defensive coach. He has been able to implement multiple different styles of defense throughout his NBA tenure based on his personnel, and they have pretty much always overachieved relative to their talent. His teams have finished 11th, 7th, 4th, 9th, 10th, and 11th defensively in his six years of head coaching.

    If Donovan created a no. 11 defense last season with limited training camp during the COVID-shortened preseason, a ton of roster turnover, and one practice with his new players, it’s a good sign that he can cobble together something decent with DeRozan, at least for the regular season when teams won’t be scheming as much to pick on him. 

  3. The best defense is oftentimes a good offense. The Bulls’ offense stands to be nuclear, and teams score worse when they have to take the ball out of their own basket.

    The Bulls should also be better at taking care of the ball this year, limiting transition opportunities for opponents. DeRozan and Vucevic should get a sizeable chunk of the offense run through them. They are both extremely low-turnover players for their positions and great passers. LaVine and White will likely see their playmaking duties drop off, and they both had higher turnover rates relative to peers at their positions. 

    Runouts are far and away the most efficient way for opponents to score. If the Bulls can limit those, then it won’t matter quite as much that their halfcourt defense has some issues. 

  4. Lonzo Ball and Alex Caruso are elite help defenders that should mask some of DeRozan’s mistakes. New addition Tony Bradley is also a solid big man defender that can help when DeRozan plays with bench units. 

There is a path where this plan works out. DeRozan is talented enough offensively to make up for his defensive limitations. But if this fails, then things will get ugly.

The thing about gambling is that you usually don’t get to bet on a great outcome without risking great pain. Safe outcomes are overrated anyway. Let’s see what happens when the Bulls go all-in.

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