Mr. & Mrs. Stephenson: Kitchen Table Baseball Scheduling

For over 20 years, the fate of every baseball game on the calendar wasn’t in the hands of some software or spreadsheets in MLB offices. It was in the hands of a married couple working from their living room in Martha’s Vineyard. In an age before AI and software optimization, Henry and Holly Stephenson built each MLB season by hand—one pencil mark at a time. This episode tells the story of the duo who quietly ran the show behind the scenes. In this episode, we tell their story and then play the quiz game with Magician, Paige Thompson! 

In 2005, the National Football League scheduled the New Orleans Saints to host the New York Giants in Week 2 of the season. The game was supposed to take place in the Louisiana Superdome. But just three weeks before kickoff, Hurricane Katrina devastated New Orleans. The Saints suddenly had no stadium. In a scramble, the NFL moved the game to Giants Stadium in East Rutherford, New Jersey. But officially, it was still a “home game” for New Orleans. The Giants ran out of the visitors’ tunnel. The Saints had the home crowd—except they didn’t.

That year, the Saints had to relocate their entire season. They played in three different cities: San Antonio, Baton Rouge, and New Jersey. And someone had to schedule all of that—while making sure stadiums weren’t double-booked, teams had time to travel, and TV partners still had viable games to air.

That’s the kind of chaos that makes you appreciate what a working schedule means.

Or how about this: In 1971, the Cincinnati Reds and the Pittsburgh Pirates played the first-ever Major League Baseball game at night in the postseason. And the only reason it happened? The television schedule. NBC wanted prime time coverage. Suddenly, the League Championship Series—an entire round of the playoffs—had to be flipped on its head to accommodate a TV slot.

Behind every game, there’s a spreadsheet, a whiteboard, a conference call. And for a long time in Major League Baseball, those things didn’t live in a corporate office.

They lived in the Stephensons’ living room.

From 1982 to 2004, Henry and Holly Stephenson were the couple behind every Major League Baseball season. Their names didn’t appear on any box score, and they were never thanked during postgame interviews. But their work made it all possible.

Together, they scheduled 2,430 games per season, coordinating 30 teams, dozens of stadiums, hundreds of special events, and millions of moving pieces. And they did it the hard way.

Henry and Holly lived in Martha’s Vineyard, off the coast of Massachusetts. Henry had a background in architecture and urban planning; Holly was a math major from Cornell. They met in New York City in the 1960s and started working together on projects like school bus routing, NBA schedules, and even NHL travel planning.  But their big break in baseball came in 1981.

That year, MLB had grown too complex for its in-house schedulers to manage alone. The league reached out to the Stephensons, who had already impressed NBA executives with their uncanny ability to solve what’s called a “constrained optimization” problem – that is, when you have too many needs and not enough flexibility.

The Stephensons took the challenge. And for the next 23 years, they ran the show.

But this wasn’t just plugging data into a spreadsheet. The couple built the schedule by hand. They used graph paper, pencils, and intuition. They’d lay out 30 rows—one for each team—and 162 columns for the games. Then they started fitting the pieces together.

And the constraints? Oh, there were a few:

• Each team had to play 81 home games and 81 away games
• No team could play more than 20 consecutive days without a day off
• Travel had to be minimized—not just for cost, but to keep players fresh
• Special requests: The Red Sox always wanted a home game on Patriots’ Day; the Blue Jays wanted to be home on Canada Day
• Stadium blackouts for concerts, circuses, state fairs, or even Papal visits
• Interleague play? That came in 1997, adding even more complexity

And the kicker? Every team made their own requests.

Sometimes they were reasonable—“We’d like to avoid a West Coast trip after a Sunday night game.” Other times? Less so. “We want to open and close the season at home, and not play more than 7 road games in a row.” Multiply that by 30 teams, and you get a pile of conflicting demands.

Henry called it “a jigsaw puzzle without all the pieces.”

Each year, it took them three to four months to finalize a workable draft. MLB would then send it to the teams for review. More feedback. More revisions. More red ink.

But the Stephensons pulled it off—year after year.

They weren’t just logistics managers. In a way, they were diplomats. They had to balance team needs, league priorities, player unions, stadium contracts, television deals, and fan experience.

They did it without software. They didn’t trust the early scheduling programs to understand nuance.

As Holly once said, “A computer doesn’t know that the Dodgers don’t like playing in San Diego on Sundays.”

But by the early 2000s, that paper-and-pencil approach was about to meet its match—an algorithm developed by math professors and AI researchers. Could technology finally replace the baseball couple?

In 2004, Major League Baseball decided it was time to modernize. The scheduling contract was awarded to a new player in town: The Sports Scheduling Group, a firm that used advanced algorithms, linear programming, and academic brainpower from schools like Carnegie Mellon and Georgia Tech.

This new software could process thousands of permutations in a matter of hours. It could optimize for travel miles, reduce back-to-back road series, and make sure TV markets got high-value matchups on weekends.

The Stephensons understood. They had always known their approach would be temporary. In fact, they’d been preparing for it. But it was still bittersweet.

After 23 years, they stepped down.

And the next year, the schedule came out—courtesy of an algorithm. The games still got played. The teams still traveled. The fans still showed up.

But something was different.

Some teams noticed that the schedule felt off—certain road trips were unusually long, or travel days felt out of place. The software had optimized mathematically, but it hadn’t yet learned the culture of baseball.

It didn’t know that opening day at Wrigley mattered more than a day game in June. It didn’t know that rivalry games draw different crowds depending on the day of the week. It didn’t know that there’s such a thing as baseball sense—something the Stephensons had in spades.

Today, MLB uses a hybrid approach. Computers handle the brute force, but humans still make final tweaks. And many of the best practices? They trace back to Henry and Holly.

The Stephensons were more than just schedulers. They were storytellers.

Each year, they built a framework on which 30 teams could create 30 different journeys. They made sure the season unfolded with rhythm. They weren’t chasing perfection—they were chasing balance.

When Henry passed away in 2015, obituaries remembered him not for any single game, but for the fact that he made all the games happen.

And Holly? She’s still on Martha’s Vineyard. Still sharp. Still smiling when baseball season rolls around.

So next time you look at your team’s schedule and say, “Hey, we’ve got a brutal stretch in August,” just remember—there was once a time when one couple, sitting at their kitchen table, made that decision. With pencils. On paper. And a whole lot of heart.

The Internet Says It’s True.

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