Since it’s primary season and so many people are obsessed with Donald Trump, I thought I’d trot out the one time my career crossed paths with him. Kind of, anyway.
In the fall of ’07, I was running the Hula Bowl, which at the time was still the No. 3 all-star game. Part of my job was trying to start a buzz around Honolulu, hoping to generate ticket sales and sponsorships, so I decided to reach out to the Rotary Club. My hope was that associating with some of the movers and shakers of the city’s business leaders would create a few synergies. I will never forget addressing that group, about 200 strong, in the ballroom of a downtown hotel. As I looked out at the audience, they sat with their backs to a series of bay windows looking out on white sandy beaches, and as I spoke, gentle breezes blew across the waters. What a cool view that was.
Anyway, one of the people I met that day was a man named Jesse James. His was a name that was easy to remember. He was a good guy, very engaging and friendly, and he offered to help me build a few relationships that might help get me connected locally. I was happy to take him up on that. As I recall, he introduced me to several people at local restaurants that helped out with meals for the players, as well as several other people.
That fall, I’d come to the island for a week at a time to conduct business and gin up excitement about the game before returning home, so one day he invited me over to his apartment for a drink. I couldn’t say no; he had been terribly friendly and helpful. At the time, I knew he had a sales-related job, but didn’t know exactly what he did.
Shortly after I arrived at his high-rise apartment downtown, that became crystal clear. I remember he welcomed me in and showed me to a table in his kitchen, providing me with a beverage. He then pulled a large signboard from behind his furniture. On it, Jesse had diagrammed an extensive plan for a hotel and entertainment complex in American Samoa. He was charged with finding investors for the project, and he hoped my boss, the Hula Bowl’s owner and a purported multimillionaire, might be interested. The centerpiece of Jesse’s pitch was that Donald Trump would be involved.
I knew my boss would not be interested, but I played along. “When is Trump coming down?” I asked.
Jesse made it clear that Trump’s involvement would be very superficial. In fact, Trump would not be integral to the project. Basically, Trump had sold his brand to the people that surrounded the project, and they hoped that his clout would help them find investors. He had already made his money on the project, and though it looked like he was an investor himself, he wasn’t anything of the sort. He had cashed a check, and now, if they found investors, his name would be on the buildings, at which point he would case more checks. He had no skin in the game. He couldn’t lose.
If there’s anything I take from that moment, it’s that Trump has become a master of being all things to all people without having to make any real sacrifices. It’s interesting that his sales pitch during primary season has been successful in creating buzz for his brand, while he hasn’t had to come out of pocket for advertising. I guess that’s one positive thing you can say about him, if nothing else.