• Choose a category
• All
• Classic-Fiction

By Root 2103 0

for the Celtics, and he took me to games. I just assumed I was going to play for them. But my backup plan was writing a sports column. I was always writing as a kid, I was always reading the best sportswriters, and I had every sports book from the last forty years. I had a popular column in college, and this was the early nineties, the toughest point probably to break into newspapers because everybody had the same idea: “I’ll go to college, I’ll write, and then I’ll work for a newspaper.” I worked at the Boston Herald for three years, covering high school sports and writing features, but it became pretty clear to me that nobody ahead of me was leaving. It was like being on an NBA team where you don’t get to start until you’re forty-five years old.

So I just kind of gave up, and in 1996 I decided to leave. I didn’t know what I was going to do. I started bartending, but I felt like something was missing. So I started a website that you could only get with an AOL account. It was with this website called Digital City Boston. At the time, the thinking was it was going to be an electronic newspaper.

I was killing myself, and making $50 a week, but in two years, I built my audience to two thousand diehards, which sounds low now, except that there weren’t a lot of people online at the time. By 2001, I was up to, like, fifteen or sixteen thousand readers, and that’s when ESPN came calling. It’s funny; the reason they came calling was because in February of 2001 I was doing these running diaries, where I’d watch something on TV and just write down my thoughts as it happened. Now it’s called the live blog, but at the time I’d write everything down and hone it and keep the best jokes and then that’s what I’d post. And I did this scathing diary of the 2001 ESPYs, I just killed it. I went after everybody. It was a terrible show. They had Joe Theismann doing comedy, and it was like everything people hate about ESPN. It was perfect for me; I made fun of everything. Well, somebody at ESPN read it, and it started getting passed around to the higher-ups and it landed with John Walsh, who started following me. Then he went back and read all my columns.

JAY LOVINGER, Editor:

When I got to ESPN and started working on the Internet, I realized two powerful things about being an editor on the Web: it got rid of the tyranny of time, and it got rid of the tyranny of space. You could run stuff as long as you wanted, and you realized that when you weren’t spending a huge amount of time trying to fit text into some kind of arbitrary hole, you had twice as much time to do meaningful work. Not only could you close stuff and have it be published immediately, but even after you closed it, you could then go back and change things if somebody pointed out an error, or if you had something to add or remove. So for me it was really kind of liberating and even fun to edit on the Internet.

Walsh found Bill when he was doing his sports-guy thing in Boston and recommended him for our Page 2 [columns and commentary], and Simmons did some stuff for us that was really good. The first piece he ever did, “Roger Clemens, the Antichrist,” was a great piece. He started doing stuff for us on an irregular basis, and we were futzing around; we wanted to hire him, but ESPN kind of see themselves as being able to hire whomever they want, so they never want to seem in too much of a hurry unless it’s a competitive thing.

I was speaking to Bill after he’d been doing freelance stuff here for about a year and he told me he was thinking about taking a job the next week at the Boston Herald. So I called Walsh up and I said, “John, you’ve got to do something right now or we’re going to lose this guy, and that’s really going to be a mistake.” So Walsh said something like “We’re working on it,” and I said, “No, you can’t ‘work on it.’ Call him right now and make him an offer or it’s going to be too late.” So he did, and the rest was history.

Bill’s obviously good for the company, it’s just that he’s an incredibly pain-in-the-ass guy to work with. You don’t really edit him. He turns