The Windy City

On 7 November 2000 I blew in to the Windy City. The Windy City is mighty pretty, reputedly, but I didn’t see much of it except for hotel conference rooms and office suites. This was a glimpse of the life of the globetrotting businessman who has visited every great city on the planet to feast his eyes upon Hiltons and airport lounges …We joined the navy to see the world. And what did we see? We saw the sea…

I had been sent to Chicago by Mark, the second of my objectionable employers, to steal ideas from the Yanks which we could then translate to the British market. Mark had largely built his fortune through this method. I was semi-accompanied by three accountants, one of whom was marginally less humourless than the other two - a fact I attempted but mostly failed to exploit to help pass the time when our flight was delayed by four hours at Heathrow. The most humourless was a woman in her late thirties. She’ll be almost a decade older now and I’ll bet it shows.

With typical unpredictability, Mark had booked us onto the cheapest possible flight (Air India: choice of curries, William Morris-style décor, interminable Bollywood movies) but into one of the most expensive possible hotels: the towering Swissotel Chicago, located downtown by the confluence of Lake Michigan and the Chicago River on the magnificently-named East Wacker Drive.

It was dusk when we arrived. 7 November 2000 was the day George W Bush won his first Presidential election and some faction or other of Illinois-based Republicans was having a party at the Swissotel. The lobby was full of their joshings and jabberings. We fought our way through to the check-in desk where I discovered that Mark had failed to pay for my room. There must be some mistake, I said. The girl smiled blandly and confirmed that there was no mistake. I gave her my lowly HSBC credit card, more in hope than expectation. I was twenty-three years old: I didn’t have enough credit for one night at the Swissotel Chicago, never mind three. The girl apprised me of this fact, blandly. I said nothing. Behind, the least humourless of the semi-accompanying accountants semi-smiled and produced his AmEx to rescue me.

Up on the 38th floor, it’s still the most unnecessarily luxurious hotel room I’ve ever stayed in: two obese American-sized beds, a bathroom bigger than the Bristol flat I shared with my girlfriend, and the whole of one wall a picture window. Even while reeling from the Bollywood flight and the check-in humiliation, I could appreciate it. That mix of rage, confusion, gratitude and resentment was a familiar state of mind throughout the eight or so years I worked for Mark.

Outside were the lights of Chicago’s blocky beauty. Mighty pretty, the Windy City - what I could make of it. Chi-town, the Second City, Sears Tower, the Wrigley Building, the Loop, the Board of Trade Building. Al Capone’s city. Obama’s city, though I didn’t know it at the time. Muggsy Spanier’s city. I didn’t know that either, though the human world is smaller and much more interconnected than is generally realised.