Harary chose blunders illustrating executive values that "butted up against" societal trends.
"The world is changing," he said. "People expect things from CEOs now."
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Former Abercrombie & Fitch CEO Michael Jeffries failed to show care with words as well, Harary said. Jeffries retired from the company earlier this month amid sagging sales and continued furor over past comments implying the brand catered to attractive people.
Jeffries' attitude implied Abercrombie was not a "value-driven company" during his tenure, Harary said.
Harary included Sears CEO Eddie Lampert, who he said exhibited flawed leadership. Former United Technologies CEO Louis Chenevert, who was reported to have made a trip to Taiwan to check on the construction of his yacht just before he left the company in November, made the list as well.
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While he never had an "egregious" mistake, Uber CEO Travis Kalanick made the list because he failed to "come out stronger" in response to the company's controversies, Harary said.
Here is Harary's full ranking of the worst executive mistakes:
1. Donald Sterling, former Los Angeles Clippers owner
2. Michael Jeffries, former Abercrombie & Fitch CEO
3. Eddie Lampert, Sears CEO
4. Louis Chenevert, former United Technologies CEO
5. Travis Kalanick, Uber CEO
Sterling and his company did not immediately respond to a request for comment from CNBC.