Meet Mike “the Mouth” Massotto – the man trying to save fantasy baseball’s live draft tradition

It's a Friday night in March. Mike Massotto, the 58-year-old CEO of a dental consulting company, is waiting for his guests to arrive. On a table in a hotel conference room in Allentown, New Jersey, are 15 carefully curated gift bags. There are drinks, some food, and in the center of it all is Massotto, a stick of dynamite known among high-stakes gamblers as “The Mouth.” Tonight he's hosting his eponymous draft.

“If I tell you this, you'll be shocked. Some people don't like me,” jokes Massotto, a man whose larger-than-life personality and love of high-stakes games in the high-stakes fantasy world has created a divide the size of the Grand Canyon between his lovers and haters.

“I didn't go into it with that intention,” Massotto said when asked what it was like to become a high-profile fantasy baseball personality. “Like almost everyone else, I started playing fantasy baseball in a home league. I always looked at the fantasy baseball magazines; the National Fantasy Baseball Championship used to have one. They showed the winners with the big checks – you know – the huge cardboard checks. I saw a guy standing there, a guy from Jersey, and I thought, 'Look at this sucker. If he can look like that and win that much money, I can do it, too.'”

This led to Massotto trying his hand at high-stakes leagues, particularly the NFBC Main Event. He traveled to New York City to draft live and walked into a huge room where about eight high-stakes drafts were being held. Who, as fate would have it, will end up in Massotto's first Main Event? The dumb from the magazine, Scott Fleming. The two became close friends and of course Fleming became a founding member of the Mike the Mouth (MTM) Ultimate League. He is also the reigning champion for the past two years.

When the NFBC began online drafts, “The Mouth” was born. By constantly posting, trash-talking and bragging about his teams in the draft chats and message boards, Massotto earned a reputation as the “guy who just won’t shut up.” Between the online and live drafts Massotto would would send messages to his leaguemates when they were pressed for time to get them to vote faster. In the process, he connected with many fantasy baseball fans across the country. Some even joined MTM Ultimate.

The entry fee is $5,000, and the prizes for the top three places in the league are as big as Massotto's personality: $40,000 for first, $20,000 for second, and $7,500 for third. But at the core of the MTM Ultimate League, you'll find the same elements that make people fall in love with fantasy sports in the first place. The camaraderie, the competition, the inside jokes, the stories of triumph and heartbreak—these are the main reasons we love this silly game so much.

But Massotto is determined to preserve a dying element of the game: the live draft experience. And he's taking it to the extreme. The experience Massotto has gained from his draft reads like a list you would hear Stefon from Saturday Night Live Custom-tailored jerseys, an after-party with a steak dinner, the draft order determined by “Iron Balls” and celebrity draft announcers – a group that includes Lisa Ann, Davana Medina and Adam Ronis.

The appeal of high-stakes leagues is, of course, the money – if you win an event hosted by the NFBC, you can pocket a six-figure paycheck. But when you talk to veterans of the draft, another theme becomes clear – these people all really like each other. Even the ones who “hate” you will still hug you and ask how your family is. And that's largely due to the “live” element.

As league hosting services have evolved in technology, it has become easier to conduct drafts and auctions from home. Instead of traveling to sit around a table with friends and spend hours picking a team, drinking, and generally being a bon vivant, you could roam around the house with your laptop and pop into the chatroom at will. But nothing compares to the live drafts and the camaraderie they generate. And Massotto not only knows this, he does everything in his power to keep it alive, including spending money on all the extras and inviting 14 people he may barely know to his home.

Most leagues have memorable histories and traditions. But not every league has a character roster that includes a billionaire, an ice cream man, and a “mad scientist” who shows up to the draft with a bag of apples and a bottle of warm orange soda.

Even COVID-19 couldn't stop them. The outbreak of the pandemic coincided with fantasy baseball draft season (mid-March 2020), and the NFBC canceled all live drafts in New York City and Las Vegas. But that didn't stop the MTM Ultimate League from drafting live. Masked and determined, they traveled to NYC anyway, where league member David Einhorn opened his offices in Manhattan. The draft took place in a Greenlight Financial conference room, with Einhorn providing catering.

There are many MTM Ultimate League draft day elements you'll see at any live draft across the country. The energy is high, the music is loud. Laptops, iPads and papers are scattered across tables, reflecting preparations for draft day. There are snacks, the league trophy is on display for all to see, and bittersweet stories are shared about narrowly missed titles and season-ending at-bats.

Name tags stand next to small plastic buckets filled with a variety of baseball goodies: decks of cards, Cracker Jacks, Big League Chew and sunflower seeds. The Stanley Cup-like trophy carried by the league champion is engraved with the names of past champions.

The league, which is by invitation only, has an annual waiting list, with returning members having first refusal. Four of the original league members remain. Each new league member receives a custom league jersey, black with “Ultimate New York” in gold-on-black letters on the front. Only members from the inaugural season in 2012 have the original: a white jersey with “New York Metropolitan Fantasy Baseball League Inaugural Season” on the front and their name — and the team name — on the back.

To prevent fantasy managers from knowing their position in the draft before draft day to give them time to strategize, Massotto developed the “Iron Balls” method of determining draft order. When your name is randomly selected, you get to choose your draft slot (known as the Kentucky Derby Selection). He thought it would be fun if everyone knew their position five minutes before the draft.

“If you’re that good, you can immediately secure your draft slot, sit down and go from there,” he says.

Over the years, some unique individuals have participated in the league. Professional gamblers. Billionaires. The ice cream man brought ice cream sandwiches to hand out to everyone. And the “mad scientist” (who, according to Massotto, was actually a retired plumber) made quite an impression in his first year in the league.

“He comes in at the last minute, his hair all messy, and sits down next to me,” Massotto says. “He has a bag of apples, a bottle of orange soda and a bunch of paper flying out of a book with scribbles all over it. He could have been an axe murderer.”

And then there's the “Curse of Scott,” which Massotto himself conjured up. Before the 2021 draft began, Massotto turned to celebrity draft host Adam Ronis to help with a joke. The plan was that Ronis would call out Scott's name no matter whose ball was selected first in the “Iron Balls” draft order (Scott was known for complaining every year about having a bad draft pick). Ronis obliged, called out Scott's name, quickly corrected himself and said the correct name. Massotto says today that joke was a mistake, messing around with Jobu's rum. Scott won his first championship that season and has won every season since.

A prominent draft moderator once announced: “There are a lot of (expletive) weirdos in this room.” He meant it as a compliment.

The league traditionally heads to Manhattan around midnight to celebrate after the draft, exchanging barbs and comparing teams over a steak dinner, cigars and maybe a drink or two. This year, however, that was changed to a catered event in a slightly more intimate setting – the 2024 edition was held at “The Godfather Estate,” also known as the Massatto residence, just minutes from the hotel. Attendees hung out into the wee hours of the morning, talking about the draft boards.

“I couldn't get them to go,” Massatto said. “But that's the point, you know? It's unforgettable. They'll tell you it's the best draft the NFBC has to offer. And that's what makes it so great. You're competing with some of the best players in the world, but they're also some of the best people you'd ever want to meet. Of course, it's great to win the money, but the experience is what makes every minute of the effort worth it.”

(All photos via Mike The Mouth)