Like many things in life, sometimes you do the sure thing, and sometimes you take a gamble. On Tuesday night, I had planned to do the sure thing: cover the rally in Grant Park and try to find a unique angle on it to let the audience experience the historic evening on their computer screens.
But then there came the slim possibility of an exclusive moment that I could capture on tape. We decided to gamble.
And the gamble meant I had to stay in my hotel room for several hours, ready to move at a moment’s notice to set up at a location nearby. I paced while we waited for a yea or nay from the campaign, watching the crowd gather on CNN, even though it was only a few hundred meters away.
We waited for hours. The greenlight never came.
I lost the bet.
I had planned to spend the hours that day and evening prepping and shooting at the rally site. I wanted to capture the sunset, the arrival of thousands of people lined up to join the rally, the anticipation among supporters — Would he win or lose? Would it be a nail-biter or a blowout? — and see the arc of the evening play out to the climax with either a victory or concession speech on the grand, flag-festooned podium on a baseball field in Grant Park’s south end.
But by the time I managed to get to the rally — on a trolley crowded with screaming Obama staffers — then through the “mag” at security, my options were slim. Media were cut off from supporters by a fence. For those in the press who hadn’t paid for a space on the risers, the best spots to see the speech podium were crowded with tripods, ladders and the sharp elbows of everyone who had arrived long before I did.
And then John McCain gave his concession speech. Obama soon followed. The roar of the crowd was deafening.
I did the best I could. I focused on the crowd, and extended my mono-pod (a pole to put my camera on), and waved it over the throngs as flags waved around them. I could see the speech on the jumbotron.
Luckily, Steven Gray and Silas Tyler were out with the crowds, talking with Obama supporters and Chicagoans who had come to witness what, win or lose, would be a historic event.
We combined our footage in this video segment for TIME.com.