Podcasts

There are many narratives about Simmons—that he’s a godsend, an innovator, a genius, a workaholic, your favorite writer … or that he’s a racist, a misogynist, a frat boy from Boston, a multimillionaire who navigated through a dying industry for his own profit.

Here’s one more narrative to consider. “He’s an only child,” Jarod Hector said to me on the phone Tuesday morning, by which time “Bill Simmons” was well and truly trending on Twitter. “That always seemed like a big part of it.”

I have worked in a small industry with Bill most of my adult life, and with Bill at ESPN for the better part of a decade. I have flown across the country to meet with Bill, read Bill, listened to Bill, been to team-building dinners and Finals games with Bill, asked Bill’s advice, managed people who went on to work with Bill, and even read articles about Bill’s many houses. I have sat in meetings about how to deal with Bill, tried to collaborate with Bill, been in torturous email threads about Bill, and had sleepless nights mad as hell at Bill. And mostly I have been confused about Bill.

But only when I listened to Jarod did Bill make succinct sense.

In the hours after I heard it, I called a few people who worked with Simmons and know him well. Everyone nodded along. Only child. There’s nothing wrong with lacking siblings, of course. Only children are innocent. But the stereotype I’m raising suggests sometimes they are coddled, and coddling can make them difficult. Bad at sharing.

In his time at ESPN at least, the coddling was off the charts.

ESPN acquired TrueHoop in February 2007. Every year, TrueHoop’s biggest traffic came on NBA draft day. There was a fair amount of planning. NBA editors had worked it out a way we could all do our things without stepping on each other’s toes. My assignment was to attend the draft, where I’d do some kind of liveblogging.

A week before the draft, family invited us to stay in a borrowed beach house at the Jersey Shore. My kids were little, at home we barely had air-conditioning. This was a nice change, being in a busy time of year while raising a one- and four-year-old. Each morning, I commuted a few blocks to the public library, where I was glued to the laptop. That’s where I got a weird call from an editor, upending all of our draft plans. Hey, we had a great idea. Whole new plan, and one that was not attending the draft and certainly not liveblogging it. What was going on? Nothing, he said. It took four or five phone calls to find out: Simmons did not want me to liveblog the draft. Simmons threatened not (or, depending who you asked, never) to write about the draft if I did. I emailed Simmons, asking if we could talk. He replied he didn’t think we needed to talk, we were fine, but “i didn't want to do my annual running diary if you were live blogging it from the exact same ‘watching it as it happens’ perspective, just because i feel like i've earned that territory over the past 6 years. but they say you'll do it from a different angle so i'm fine with that.”

I was announced as the new NBA editor of ESPN.com at the All-Star game in February 2014. It was made clear to me that it was very very very important to our bosses that I get along with Simmons.

Simmons and I made tentative plans to meet that weekend in New Orleans. We had a time—9:30 am Saturday—but hadn’t fixed a place. Then nothing. Didn’t hear from him all day. Saturday night at 7:40 pm, he emailed, “At casino until 730am. Barely made my plane. Can we talk on phone this week?”

The executives wanted me to do nothing more urgently than meet Bill, so on Monday, March 10, 2014, I flew to Los Angeles. Perhaps the central crisis of ESPN.com’s NBA section at the time—at least from the corner office view—was the strained relationship between ESPN.com and Grantland. There had been casualties. My direct boss, an editor, and I would spend Tuesday laying the groundwork for collaboration.

There were challenges. I’m not sure anybody at ESPN.com ever really succeeded collaborating with Grantland. One possible reason: One of Grantland’s highest ranking employees told me Grantland’s goal was to destroy ESPN. Simmons used leverage he created when his contract was expiring to convince ESPN to write giant checks to develop … a thing in his image, of his choosing. ESPN would pay for everything and control almost nothing and Bill would show us.

Then Grantland launched and had much wonderful content. But it didn’t show us. The numbers showed niche appeal. Around that time they put up these monitors around the ESPN offices in Bristol that showed how many people were reading the most-popular stories. The Grantland stories that we heard so much about in meetings, that we promoted so heavily, almost never sniffed the top. Before too long they reconfigured the displays, so Grantland stories appeared in their own, separate listings. After an initial flourish, the word was that Grantland’s relationship with the all-important ad sales team had soured. When your startup has troubles with both audience and revenue, things can get a little tense.

Bill had pipes into the highest levels of ESPN. I encountered many a career-oriented ESPN executive who acted like pissing off Bill was the worst of all sins. The corollary: to appease Bill was to pass a kind of I.Q. test. It trickled through everything. Thus began the Great Coddling.

So I arrived at the L.A. offices of Grantland, part of the L.A. Live complex with Staples Center, and essentially a cube farm with an array of private offices and a conference room, at the appointed 11 a.m. Tuesday. Bill’s key sidekick at the time, Dan Fierman, invited me to wait in his office.

I had plenty of work to do, nowhere else to be, and a laptop in my bag. Dan was at his desk bustling away. Employees ducked in to discuss this or that.

No one had any idea when Bill would be there. There was a lot of apologizing.

At some point a very stressed man, an editor, appeared. They were doing some project around anniversaries of movies. One of the movies had two release dates—one in select markets, another nationally. There had been debate, and Bill had wanted to use the earlier date. Now, for good reasons, someone had to get across to Bill that they were going to use the later date. The meeting I witnessed, which took a surprisingly long time, was the editor and Dan game-planning how they would break it to Bill so that Bill would be mad at Dan, who evidently had alligator skin, and not the editor, who simply couldn’t stand to incur Bill’s wrath again.

At least an hour late, maybe more, Simmons rolled in, wearing carefully purchased jeans, a deniable touch of mousse, and a recommendation that we “grab Jacoby and get salads.” (I have always liked David Jacoby—especially when he invented a song one Sunday morning, at Basketball City in Boston, called We’ve Got a Guy Who Never Misses about Rob Mahoney. Mahoney now works at the Ringer.)

Blinking in the L.A. afternoon sun, Simmons had questions about ESPN’s digital videos. How many people watched? The numbers were pretty huge. At times, after much trial and error, we made big money in title sponsorships.

Simmons didn’t want to hear about how we got that done with a single video producer, nor how Grantland might learn from our mistakes. It was weird to him that ESPN could deliver that kind of traffic, but not to Grantland. He didn’t want to earn a big audience, he wanted to take one.

Aren’t there some baby birds who try to kill the other baby birds so they can get all the food?

Then he talked about some of the less-famous Grantland writers. What could we do to promote their work? I made a case for being bold in trying new things, and for meritocracy—serving sports fans first, putting the best performing work in the best spots. I noted Bill noting that I did not make a firm commitment. We stood in line, and then directed the people who filled our plastic clamshells with romaine, blue cheese, and the nuts and seeds of healthy living.

On the walk back to the offices, it came up that I was staying at the Ace Hotel. Simmons immediately mentioned the hot spot rooftop bar, where Grantland had thrown a party. He mentioned some celebrities. Then he got all excited, telling Jacoby they should invite everyone over to Simmons’ house. They could hang out by the pool, do some drinking. It would be good for the staff. It was so sunny downtown L.A. smelled good. Who couldn’t go along with that plan? Bill talked it all through until, I think we were on Olympic Boulevard, Jacoby stiffened. How can we make sure, he finally asked, that your wife is OK with this? Because you remember last time …

It struck me that Bill bet big on the primacy of his emotions. They seemed to govern everything. Were there other things to worry about? I never saw him ask anything like: “Does that work for you?” Of course, this has a lot of connotations.

Back at the office Simmons strolled around the cube farm, at one point stopping to tell me he was glad the research finally showed that the hot hand was real. The hot hand concept has befuddled Nobel-prize winners for the better part of a century, and played a role in exposing human bias in perception: We feel “hot” far more than we are. At Sloan a few days earlier, a new small study had found it might sometimes be real. Bill had known it all along, he said, because he could feel it when he played. He gave no allowance for the possibility he might be biased.

As Bill and I talked, he ambled over to the desk of a staffer, and dug around until he found an unopened pack of gum among her things. “Do you want some?” he asked me. She was sitting right there. He had not asked if he or I could eat her gum. Sometimes in awkward moments I joke; sometimes it goes badly. “Is this man eating your gum?” She laughed a little, and said she didn’t even like gum. She only bought it for Bill. By this point, he was loudly chewing and had littered the wrapper on her clean desk, a foil turd, staining her dignity.

Insanely, I doubled down on the “comedy”: “This seems like an abusive relationship!” Fun over. She couldn’t talk. Bill immediately turned and walked away. What had just happened? Not too long after, she quit and moved away from Los Angeles.

Grantland Day rolled on. There was a meeting with Bill, Dan, and my boss in Bill’s definitely-the-biggest office. We had proposals for things we could collaborate on, one of which was HoopIdea. We had already had big success with it, real rule changes in the NBA and an ongoing conversation. It was a catch-all term for proposing rule changes; Grantland NBA writers loved those topics. Blank stares.

We got to sit in a Grantland editorial meeting, which mostly served to illustrate how resource-rich Grantland was. Illustrators and animators standing by for fun stuff, dedicated studios standing by to record audio and video. ESPN had reopened its NBA rights negotiations to get Grantland additional rights. We were a long way from Bristol.

I followed up with a short email thanking them for the time and the salad, and summarizing ideas to collaborate. No response. Eventually I ended up on the phone with Fierman. He started talking fast. He said he thought we weren’t thinking nearly big enough about HoopIdea, and bragged that the ESPN TV programming people were eating out of their hands, would do whatever they wanted, and they had talked to them about … dramatic pause … turning HoopIdea into a TV show.

This made no sense. But OK. The programming team at the time was three people that I met with by phone or in person every week or more. My boss and I happened to see them in person a few days later. Did you happen to have any conversations with Grantland, my boss asked them, about HoopIdea?

“HoopIdea?”

On June 30 of 2014, on Grantland Zach Lowe published a story with a headline about Jason Kidd. Lower down was leaked intelligence about the profit and loss of essentially every NBA team. It was incredible reporting. Real news. And a dilemma: ESPN’s News staff is serious business. It’s a separate organization with dozens of full-time professional editors and their own set of rules. They managed not only the headline stack but also influenced what news stories made it into SportsCenter and the Bottom Line. There were protocols, meetings, and reminders about publishing news when we found it. On ESPN.com you’d be in big trouble if you published news buried deep in some other story without first notifying the news desk. (I was guilty of this sometimes myself.) You could even be in trouble if you knew breaking news and didn’t tell them. And you’d be on the phone with a news editor who would vet your sources.

But Grantland had different rules. There was no suggestion Zach would be in trouble. Instead, the bosses of the people who enforced those rules wondered if doing their jobs would get them in trouble. The biggest editors overseeing a staff of nearly a thousand people fretted over Bill’s “wrath” (that was the word used) if they made a news story about NBA teams losing money. Would Bill see it as cannibalizing Grantland’s traffic? They decided against a newser.

At that time, all we knew for sure was that the future of sports media would be very different from the past. Studios and game stories weren’t it. It was the right time to identify new voices and to invent new products. Grantland put some energy into that, and had some success. It wasn’t clear to me yet—foolishly—that the leadership breakdown at ESPN meant Bill would have a near-monopoly on ESPN’s spare resources to try new digital things.

But Simmons’ operations have not been hotbeds of innovation. Jason Concepcion’s NBA desktop is a delight, but saving this business will take a hundred more innovations like it.

Simmons directed much of his effort to old-school vanity projects. He bullied his way onto NBA game broadcasts where he made everyone squirm by sulking, “do I get to speak now, it’s been like ten minutes.” Who knows how much money was spent on Grantland concept TV shows. Barack Obama had some interest in reaching sports fans—Simmons muscled things so that he got the interview. He somehow convinced the world that he invented the sports documentary and got himself a credit on every 30 for 30.

I don’t know Bill well; I respect a good number of people who think he’s tremendous. We are all mixed bags. But I am certain that the secret sauce of his ascendance in the media world was not his early pivot to podcasting, his idea to make sports documentaries, or his keen eye for talent. Instead, his key skill has been gaining leverage over the higher-ups. Many have tried to extract millions and carte blanche decision-making power from ESPN honchos. Bill was just better at it, at least for a while.

I wonder how many of his partners through the years—investors, executives—ended up better for it.

He’s an all-timer when it comes to figuring out who matters and cozying up. He gets good seats to NBA events, and sits in them with people who can do him favors and write him checks. (You don’t often knock into someone like Simmons in a press room, but when I saw him at a 76ers game a few years ago, he was there leading around Jim Bankoff, the CEO of Vox, who gave Simmons some kind of deal.)

William Wesley—gatekeeper to many a big name—was a great person for Simmons to know. Simmons realized the importance of Wesley at some point and made sure to get close. Somehow Simmons got the impression Wesley never talked to any reporters except Simmons, which was hilarious. Wesley’s contacts include a hundred or a thousand journalists—many of them have told me about their nights gambling with him or the time he was on their radio show in Louisville or whatever. On the floor after some Finals game, as Jade Hoye and I were setting up for TrueHoop TV, Wesley and I small-talked a bit. Then Simmons appeared. He put his face right in mine and told his big dumb secret: Wesley didn’t talk to any journalists except Bill … and me. This was just silly. I met Wesley’s eye, he grinned.

Wes is no dummy. Later Simmons ended up inking some kind of deal with Wesley’s CAA. But what was this play? How did he read Simmons? Who would need to be told there were no others?

An only child.