Barack Obama & Kanye West at a 2014 DNC Fundraiser

Dan Pfeiffer tells an unforgettable story that is somehow even crazier today.

Dan Pfeiffer, former Obama WH Communications Director and current co-host of Pod Save America, wrote the book "Yes We (Still) Can" in 2018. 

With all the Kanye, Kim K, and Elon insanity I've seen recently, it reminded me of a four-page interlude in the middle of the book that, at the time, I found to be so funny, but seven years later, it feels ominous at best.

Dan describes a scene in 2014 when Obama and his staff flew to LA for a fundraising event. The event took place in the library of an LA mansion, so we're talking big-money fundraising efforts. 

Prior to the event, Obama Deputy Chief of Staff Anita Breckenridge got an email from someone on the WH political staff about a few guests who wanted to attend. "They will write checks. Are we OK with this?" they asked. Anita turned to Dan to ask the same question, which was essentially, would Obama be OK with Kanye and Kim Kardashian attending this fundraising event?

After running through a million scenarios, including Kanye's support during the 2008 election and the hot mic comment Obama made following Kanye stealing Taylor Swift's moment at the 2009 VMAs in which Obama called Kanye a jackass, Dan told Anita, "Let's tell them no and see what happens."

The hosts said they would cancel if Kanye and Kim couldn't come, so, according to Dan, "We gave in pretty quick."

The roundtable event had about 25 people in attendance, including Leo DiCaprio, who was interested in climate change policy. Obama answered all sorts of questions while Kanye and Kim stayed silent. However, as the event wrapped up, Kanye's hand shot up. "Last question goes to Kanye," Obama said.

Kanye's question was almost 30 minutes long, talking about the similarities between him and Obama (Chicago, haters, rivals - Obama had Republicans, and Kanye had Drake). But the line I found most fascinating was this; "The only way to get things done is to get the best people together. Me and Jay on the mic. Mario Batali on the pasta and we need Elon Musk." 

Eventually, Obama took advantage of a pause in Kanye's breath and thanked him for his thoughts, acknowledging his good thoughts, especially about the value of meeting with smart people like Elon Musk.

When I read this book, I'm not sure I knew who Elon was, certainly like we know him today. Still, given Kanye's obsession with Elon's similar obsessions, I can't help but wonder how in the world Kanye and Kim went from giving money directly to the DNC as recently as 2014 to Kanye quite literally obsessing over Nazis. Even Kim strategically posing with a Cybertruck made famous by another man who loves flirting with Nazi symbolism. 

As we've seen, power is a dangerous drug. Between Kanye, Kim, and Elon, I think it's fair to say that a big common denominator between the three is their obsession with staying in the spotlight, shock and values be damned. That's why our pointing out hypocrisy rings hallow. Their actions ARE consistent with their values as their values are rooted in money, not morals. 

Anyway, the fundraising event ended, and Dan hopped into the Presidential limo with Anita and Valerie Jarrett. Dan wondered what Obama thought. Was he annoyed he had flown across the country to sit in a room with rappers and movie stars while listening to Kanye rant for 30 minutes about drinking fresh-pressed juice in Japan? I mean, we're talking about the President of the United States here. 

Then, Obama broke into a huge grin and said, "That shit cray."