Like the President, Steinbrenner liked to mix family and business. Steve Swindal was supposed to take over as the head of the Yankees before he and Jennifer Steinbrenner split up. Now his two sons are running everything. “I have no intention of retiring,” Steinbrenner boasted in 2007, “and my family runs the Yankees with me.” (Also, please “go buy Ivanka’s stuff.”)
The two men also sound almost identical in their backhanded praise of successful subordinates—and desire to claim credit when things go right. “He was fired in three places before we hired him. …People said he didn’t know what he was doing,” Steinbrenner said about Hall of Fame baseball manager Joe Torre. “Believe me,” he might have added.
Steinbrenner was a clean freak, much like Trump. “Steinbrenner hates dirt. In one of the few interviews that his wife, Joan, has ever given, she revealed that he liked her to vacuum their home several times a day,” observed The New Yorker’s John Cassidy. (Cassidy’s 2002 article on Steinbrenner is a treasure trove for anyone looking to compare him to Trump. Take this line, for example: “Steinbrenner’s rule, like those of many despots, is marked by surprising acts of kindness.”)
But the real comparison might be Trump having won the presidency with three different campaign managers, and the very early resignation of National Security Advisor Mike Flynn.