Biff America column: Tips, driveways and desperation |

Biff America column: Tips, driveways and desperation

Johnny First Round has more money than God.

“First Round” isn’t John’s real name. I gave him that moniker 30-plus years ago when I worked at a restaurant in the Hamptons on Long Island. The assumption being if you were lucky enough to wait on Johnny, then you would be buying the first round of the staff’s post-shift drinks.

He usually would come in with a group of friends, almost always paid and tipped like a crazy person. He did this with no show or bravado, nor expecting special treatment.

John’s pedigree and personal life were well-known: family money, prep schools, Ivy League college and grad schools, Wall Street and a stint as a presidential advisor.

I waited on a lot of wealthy and famous folks that summer. Johnny is the only one with whom I kept in touch. Most of this was happenstance. His house in Connecticut is in the same town where an old friend lives, and his summer home on Martha’s Vineyard is not far from my in-laws’ house.

Support Local Journalism

It was the day after the 2004 election. My mate and I were home mostly for the World Series. The Red Sox had clinched it in St. Louis a few days before. If they lost and returned to Boston for Game 7, then we would have been Johnny’s guests in his box seats.

George W. Bush’s re-election took some of the luster off the Sox’s victory. We liberals pretty much got our butts kicked in congressional races. I wanted Kerry to win, but I did, and do, feel W. Bush was a good man. I can remember being disappointed with the results, but my grief was tempered by the fact that the Sox had broken the Curse of the Bambino by winning their first World Series in 86 years.

We had stayed up late the night before, but our flight home was out of Hartford, so we still had plenty of time to stop in for a late breakfast at John’s house on our way to the airport.

We could see the large home in the distance as we drove our rental car up a quarter-mile, winding driveway. There were two life-sized brass statues under an archway in front of huge wooden doors with Kerry-Edwards hats. Ellie said, “We probably don’t have to lock the Kia.”

The housekeeper let us in and brought us to the sunroom, where John had silver coffee urns, juice, pastries and quiche set out. He was wearing slacks, a white linen shirt and a cotton V-neck sweater; he looked tired.

Different Realities

I’m guessing he gave many thousands of dollars to the losing candidates. Though this happened more than 10 years ago, I remember how he looked and what he said. He was sitting at a table with the New York Times spread out. He ran his hands through his perfectly cut salt and pepper hair as his Cartier watch caught the light and said, “How could this have happened? I have never felt that I had less in common with the average American.”

If Johnny First Round saw me fighting off laughter, he didn’t mention it. What I wanted to say was he had absolutely nothing in common with the average American. At the time, I thought I was different.

If nothing else, then this past election has been a wakeup call that you don’t need to live in a mansion to be disconnected from what almost half of our nation is feeling. I was shocked and dismayed over Donald Trump’s election. We have elected a POTUS unlike any other in my lifetime. And that should tell us all something.

It should tell us that many Americans are disenchanted with the status quo, angry with a disinterested government and (in some cases) desperate. The fact this could happen means both sides have not been paying attention. The good news is that Americans, elected or not, are now becoming engaged and aware of those who reside outside the small bubble of our lives. Both sides would be well-served by empathy.

You don’t have to have been included in the ranks of the angry and disenfranchised to understand their struggle. And certainly we can all feel for a guy with a quarter-mile driveway. Imagine what a pain it would be to shovel snow off that thing.

Jeffrey Bergeron, under the alias of Biff America, can be read in several newspapers and magazines. He can be reached at Biff’s book “Mind, Body, Soul,” is available at local shops and bookstores or

Support Local Journalism