February 21, 2018


In football, a team’s playbook is sacred, a three-ring-binder bible filled with secrets and strategy, entrusted to new players and guarded with vigilance. The playbook is both a record of a team’s philosophy and a briefing book packed with information — what is known about opponents, and how to defeat them.


Donald Trump has a playbook, but he doesn’t even try to guard it. He leaves it sitting wide open to the very best parts, for any of us to read. It’s his Twitter feed, and a quick glance reveals the president is running 2020 plays and anticipating a title match against an opponent he’s truly afraid of: Oprah Winfrey.


“Just watched a very insecure Oprah Winfrey, who at one point I knew very well, interview a panel of people on 60 Minutes,” Trump tweeted late Sunday. “The questions were biased and slanted, the facts incorrect. Hope Oprah runs so she can be exposed and defeated just like all of the others!”


In fewer than 50 words, Trump reveals volumes about his plans for 2020 — and the candidate he’s truly afraid of facing.


During the 2016 campaign, Trump famously clashed with then-Fox News anchor Megyn Kelly, and to this day he seems fixated on Hillary Clinton. During the primaries, Republican rival Ted Cruz said, “Donald does seem to have an issue with women.”

In Oprah Winfrey, Trump sees not just a strong woman, but a successful one who has Trump’s wealth and power as well as arguably a greater mastery of the media. On CBS’s 60 Minutes Sunday night, Winfrey interviewed a panel of voters about the first year of the Trump presidency. In the segment, Winfrey displayed the same authoritative control of differing opinions that she did on her long-running television show, getting at the feelings that Trump inspires in his supporters and how they hear what he says very differently than Trump’s detractors.


Oprah wasn’t insecure; she was in control. In a discussion of sexual harassment and the candidacy of Roy Moore in Alabama, Winfrey displayed her ability to talk to people of varying opinions and get others to listen: “So for those of you who are not Trump supporters, can you hear what Jeff just said? Can you hear that?”


What Trump hears in Oprah is clearly the voice of a person who can grab people’s attention, just as Trump can, and manipulate the machinery of modern media to her own ends, just as Donald Trump has. But where Trump focuses most if not all of his energy on his core group of die-hard supporters, Winfrey’s appeal may be broader, with talents honed in years of doing interviews and hosting her talk show to engage with people no matter their beliefs. Trump, in comparison, mostly talks about himself and tries to shrink his opponents into caricatures.


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