How fantasy football exploded online and kept Yahoo relevant

InTales of the Early Internet
, Mashable explores online life through 2007 back before social media and the smartphone changed everything.
When’s the last time you used Yahoo for…anything at all? Your answer might just depend on a simple question: Do you play fantasy football?
That’s because even as Yahoo has faded toward internet obscurity, it remains an absolute powerhouse in fantasy sports. 
Years ago, in the early-to-mid 2000s, fantasy football boomed in participation for a single reason: the internet. And back then, Yahoo was still a very big deal. So, here were are, millions of sports fans, glued to a Yahoo app in the year 2020. And that’s likely not changing any time soon the product is actually pretty damn good despite coming from a brand most don’t use anymore. 
“There’s never been a conversation about, ‘Hey, let’s switch to another format,” Todd Paonessa, a 49-year-old in California who has been playing in a Yahoo league for 14 years, told Mashable. “Yahoo does make it easy…We’re a bunch of lazy old farts now and to actually adapt to another format would be inconceivable. I think we’d quit playing rather than switch to another format.”
“I think we’d quit playing rather than switch to another format.”
Before fantasy football went online it was an absolute chore to play. Not to get too far into the weeds here, but it was basically taking up math worksheets as a hobby. You had to parse through newspapers to get the previous day’s box scores then manually score out a fantasy game player X scored a touchdown, it was a rushing score, that’s worth Y, give team Z those points, over and over again. It was for obsessives, not casual fans. It was like Dungeons and Dragons for those with jockish tendencies. 
The internet and, in part, Yahoo brought the game to the masses. 
When Yahoo was king
A quick history lesson: The initial fantasy rules were invented by Oakland Raiders staffers and a reporter, who then played the first season in 1963. By 1989, over a million diehards were playing in total, according to a report by the San Diego Union-Tribune. Throughout the ’80s there were lots of different rule-systems and it was, well, confusing, to play fantasy football. It was when fantasy football moved online around 1997 and a computer could do all the math for you that things really took off. And Yahoo made perhaps the most important decision: It made its fantasy football product free in 1999.
In the pre-Y2K world, there was hardly any tech company as important as Yahoo. It was the web’s primary search engine, a major email provider, and the web’s second-most visited site behind, you guessed it, AOL. Those two stops were basically the internet’s directory. 
“Our company was five years old,” Jeremy Ring, a Yahoo executive from 1996 to 2001, wrote in a memoir, according to Fast Company. “We were worth more than Ford, Chrysler, and GM combined. Hell, we were worth more than Disney, Viacom, and News Corp combined. Each of those great American brands could have been swallowed up by us.”
So when Yahoo made fantasy free, it was a huge deal. It was a company worth some $500 per share giving away this fun, new thing. 
But as the internet evolved, Yahoo didn’t keep up. It suffered in the 2000 dotcom crash, then infamously passed on chances to purchase Google and Facebook in both company’s infancies. Yahoo did lots well, as Fast Company noted, but never really stood out in one product or made the most of advertising opportunities. By 2016, it sold to Verizon for a (relatively) measly $5 billion. It’s still a Verizon company now. 
Even through those struggles, Yahoo’s fantasy offering has persisted. That’s partly because people who play fantasy football typically love it, so they’re bound to come back year after year.
“I’m emotionally involved to a point that’s embarrassing,” Paonessa said. “And if I had spent [my] time with fantasy football [instead] playing a guitar, I’d be Jimi Hendrix right now.”
Jim Pittman, a 57-year-old in Tallahassee, Florida, said he began playing fantasy back when you had to score by hand. That really took time. Back in the early 2000s, his league moved online to Yahoo. They’ve stuck with it ever since. Part of that reason is ease why change if it works but also, Pittman said, Yahoo has done a good job of making small, helpful changes over time. 
“In particular, what I liked Yahoo for is, from a scorekeeping standpoint, it seemed like it was made for all different levels from beginner to advanced from the very beginning,” Pittman said. “And then over the last 18 years that we’ve been doing it…they make improvements to that scoring system, but they don’t make drastic improvements. They make small adjustments.”
How Yahoo fantasy football lives
To understand why Yahoo fantasy football is still around, you also need to understand the fantasy boom. 
The NFL is wildly popular. An average game gets 17 million viewers. Fantasy has become a way for fans to stay especially interested in games. According to the Fantasy Sports & Gaming Association, roughly 46 million people play fantasy football. 
In 2019, Fox Business reported Yahoo’s fantasy football had some 7 million users. Yahoo declined to share exactly how many fantasy users it has in an email.
“Its important that we continue to offer this experience for users, especially during these unprecedented times that have impacted so many facets of life, including sports,” Brian Marshall, vice president of product management at Yahoo Sports, wrote to Mashable. 
Keep in mind, daily fantasy a buzzy online betting competition that’s grown in popularity in recent years is different than Yahoo’s general Fantasy offering. Yahoo does daily fantasy too, but it pales in comparison to the juggernauts in that space, FanDuel and DraftKings. (Daily fantasy is illegal in some states.) Yahoo’s classic fantasy product has, in part, survived because friends created leagues years ago when Yahoo was a major tech player. Those leagues are pretty simple affairs: Each person makes a “fantasy” selection of players, which squares off against their pals’ teams. 
A big benefit of using Yahoo year after year is that it makes everything easy. Yahoo auto-renews your league, people can just sign right back in, and it’s familiar. There’s no fantasy provider that’s considered leaps and bounds better than another, but lots of folks really prefer Yahoo. 
Kate Rutkowski, a 32-year-old who lives in Portland, Oregon, joked that Yahoo fantasy football is the least of all evils, which includes competition like ESPN and the NFL itself. Rutkowski’s decade-old, all-women league has been using Yahoo the entire time and prefers it to providers they use in other leagues. 
“Every year you get together and you’re texting like, ‘We should switch, we shouldn’t do Yahoo,” she said. “And then the conversation just goes to how terrible everything else is and you kind of circle back and go well, I guess we should stick with Yahoo then, shouldn’t we?”
From a personal standpoint: I play in one Yahoo league and another through ESPN. I vastly prefer Yahoo’s fantasy website and app. 
AOL might’ve fully migrated to the internet’s graveyard, but its borderline remarkable that Yahoo still has something that updates in real time every Sunday for millions of people. And its product is better than companies most would likely describe as more relevant. 
History matters
There’s also one massive thing you’d lose if you switched out from Yahoo: historical data. 
Yahoo has easy-to-use tools that let you look through the history of your league. You can see how many times each person has won, how Yahoo rates your performance over time, or the playoff scores from every season. If you’ve had a league going for a decade, you don’t want to lose that history. You don’t want to trash the results from back in the day. 
Jason Bisnoff, a 29-year-old staff writer at Forbes, has been in a Yahoo league with friends since middle school. He said they keep going back to it because it’s the best site/app but also because they don’t want to lose that historical data. 
“I have a friend who is nerdy enough, he did a whole Excel sheet of who’s been the best over time. And that data is readily available, which is good to have, especially because it’s something that 12 of my best friends in the world spend six months of the year talking to each other about,” Bisnoff said. 
Nearly every person I talked with who played Yahoo fantasy appreciated having the historical data. Bisnoff’s league has taken the historical data to another level, because, as he put it, they enjoy “chirping,” or teasing, one another. That one friend who made the Excel sheet was determined to prove he was actually the best player, despite not winning. 
“He’s the quintessential guy who cares the most but hasn’t won,” Bisnoff said. “He needed to get to the bottom of how he’s better statistically than a bunch of the champions. Which led all the champions to say, ‘Well, you’re not a champion.'” 
The history of the league matters because, in many cases, it’s a history of the group’s friendship. 
These sorts of fantasy leagues aren’t about the money (like daily fantasy) or even football itself. They’re usually about bragging rights, an excuse to pay attention to games on Sunday, and a reason to talk with your friends. The history of the league matters because, in many cases, it’s a history of the group’s friendship. 
So what now? 
Yahoo has tried a number of new things in the fantasy space: It streams NFL games, it has a feature where you can watch with friends, and it added daily fantasy.
“As a tech company were able to have a huge point of differentiation in building these products, which we will continue to reimagine with powerful technologies like 5G, AR and VR,” Yahoo’s Marshall said.  
But its old-school fantasy product is what remains the most popular. 
“One of the things that has helped Yahoo to remain relevant when it comes to season-long fantasy is how sticky season-long players are,” Chris Grove, a partner at Eilers & Krejcik Gaming, a sports and gaming research firm, and founder of Legal Sports Report, a website covering sports betting and fantasy sports, told me over email. “You don’t want to have to learn a new system when it’s time for your league to boot up you just want to get to playing. Multiply that effect over the entire group that makes up a league and it’s not hard to appreciate why season-long fantasy platform winners tend to stay winners: The hassle of getting the whole group to agree to migrate to a new platform is generally not worth whatever the benefit might be.”
Grove added: “It’s worth noting that Yahoo daily fantasy never caught on to any meaningful degree.”
Yahoo isn’t the tech behemoth it once was, but it still drives web traffic and its finance site is widely used by stock watchers. And yep, Yahoo also remains great for your fantasy league. But that’s because it’s a beloved relic; the fantasy love isn’t signaling a general rebirth. 
“I have a Yahoo mail account and I don’t know how to get into it or anything,” Rutkowski told me. “But you know when you’re checking out at a store they’re like, ‘What’s your email address?’ In my head, I’m like, ‘OK, if it’s a store I really like I give them my real email address. And if it’s a store I don’t like, I give them my Yahoo.'”read more