The Cartwright Stuff

Trent Hawthorne
3 min readSep 6, 2020


Michael Jordan and the Chicago Bulls have been on my mind since The Last Dance aired in April. The most gripping scene of the series was the end of Episode 7, when Jordan emotionally opened up about his bullying leadership style. His message was clear: to get elite results, he had to be that way. And if you don’t agree with that, then you’ll never be elite.

Well, with all due respect to the GOAT, I am here to tell you that Jordan is wrong. His way is not the only way.

In his groundbreaking book The Captain Class, author Sam Walker proves this by analyzing the most successful sports dynasties of all time. The takeaway from the book is an important one for all business leaders. The best teams win because they have effective captains. Those captains aren’t always stars; in fact they’re usually unassuming. And as your company grows, identifying them and putting them in place is the most important thing you’ll do as a leader.

My favorite case study from the book? The Chicago Bulls themselves.

After a series of devastating playoff losses, the championship-less Bulls started the 1990 season a disappointing 5–6. To right the ship, Head Coach Phil Jackson appointed veteran Bill Cartwright as co-captain alongside Jordan. This was a stunning move — not only did it signal that the League’s brightest star wasn’t capable of leading the team on his own, but it also communicated that Jackson did not endorse Jordan’s approach. Cartwright was Jordan’s polar opposite, and the two made no bones about the fact that they didn’t like each other. Jordan was flash and talent; Cartwright was workman-like and stable. Jordan berated and belittled and cajoled; Cartwright stayed late at practice and chatted and coached.

Jackson’s decision worked. The Bulls won 5 games in a row following Cartwright’s appointment, and finished the season 61–21. The Bulls won their first of six titles.

Jordan acknowledged the brilliance of Cartwright’s promotion to co-captaincy later in his career, reluctantly acknowledging “Bill made the difference.”

Bill made the difference.

There are two important lessons for business leaders here. The first is that you don’t have to “Be Like Mike” for elite performance. As Walker illustrates in The Captain Class, the unifying thread among all of the teams is the existence of a hard-working, back-channeling, quiet captain. They do the jobs on the team that no one wants to do, and because they talk so little, when they talk, everyone listens. They care as much as their outspoken, star teammates, but approach leading totally differently.

The second lesson is that as your business or team grows, putting the right “captains” in place is likely the most important thing you will do. Phil Jackson is obviously a talented basketball mind, but the most important move of his career may have been appointing Cartwright co-captain. Like sports, business is about people, and people make the difference.

The captains reinforce your message. They will build your culture.

Choose wisely.


Hi, I’m Trent Hawthorne, COO at Rabbu and Founder of StandupPro. This newsletter has the one most shareworthy thing on my mind, with some commentary on why I think it matters. Simple, but hopefully powerful — which is how I try to approach everything I do.

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Trent Hawthorne

Builder of companies, high-performing business teams, & technology products. People Accelerator.