SHINY THING$ 0183 ✨

True love isn’t always candle‑lit dinners and serenades. Sometimes it looks like two people scrolling Instagram side‑by‑side, perfectly comfortable in companionable silence. 

Call it “independent togetherness”—the modern romance playbook.

At Rally, about 5 years ago we unexpectedly came across a couple that truly embodies that playbook.

You see, we move a lot of really important, really expensive items around. Items that require a very special method of transportation — bonded, insured to the maximum allowable amount, and often armed. 

The truck that carries those items requires a two-person team. It can only stop at pre-determined points, and one person must stay in the vehicle with the cargo at all times. Above all, trust is paramount. 

When we scheduled our first early morning pickup of a million dollar baseball at Rally HQ in 2018, we were surprised to see Mr. And Ms. Jones (names changed for the purpose of anonymity). A 60-something unassuming husband and wife team together for 40+ years who crisscross the highways and byways of nearly every US backroad for more than half the year, transporting some of the most valuable assets known to man. When they became empty-nesters, they took cues from their previous lives (in careers we can’t say also for the sake of anonymity) and found an opportunity to start interesting second careers, but do it together.

It became part of the glue that kept the relationship strong, and they get some good stories to head home with when the job is done.

Their story reminded us of another under‑the‑radar duo who kept baseball itself on the rails.

In a sport that is speedballing toward automation, we dedicate the 183rd installment of Shiny Thing$ to The Stephensons: the husband‑and‑wife team who created the entire Major League schedule for every team every season by hand for nearly 25 years… all from a spare bedroom.

The Schedule Makers: Henry and Holly Stephenson’s 25-Year Reign Over Baseball’s Calendar

Staten Island, New York, mid-1980s: Executives and managers ridiculed them. Sportswriters questioned their intelligence. Players cursed their name as an excuse for a losing streak. All because Henry and Holly Stephenson – a husband-and-wife duo – literally told everyone in Major League Baseball where to go. For more than two decades, this unassuming couple were the invisible architects of each baseball season’s rhythm, crafting the intricate 162-game schedule for every team.

It was, as Henry liked to joke, “a thankless job”– when was the last time you heard a manager credit the schedule for winning the pennant? – but the Stephensons embraced it with a passion that would shape not only the league’s calendar, but also their own lives together.

For over twenty years (1982–2004), this husband-and-wife team meticulously constructed each MLB season’s calendar by hand and with early computer aid. The MLB schedule – 2,430 games squeezed into 26 weeks – was their yearly masterpiece.

An Unlikely Journey to the Big Leagues

It all began with a chance meeting and a wild idea. In the mid-1970s, Henry Stephenson, an urban planner with a master’s in architecture, and his wife Holly, a computer systems analyst with a keen mind for math, were contemplating starting a home business. Fate intervened when they met George Faust – a former NBA scheduling official – because they bought a used car from his son. Faust mentioned that the NBA was desperately seeking to modernize its scheduling process. The league’s old schedule-maker, the legendary Eddie Gottlieb, still drew up the entire NBA season on the backs of envelopes and scraps of paper, and no one had yet succeeded in programming a computer to do it. Five software firms had tried and failed. Henry and Holly looked at each other and decided to give it a shot.

Neither spouse was a traditional sports executive, but together they had the perfect blend of skills: Holly had minored in math at Cornell and was fluent in computer programming, while Henry brought analytical thinking and big-picture planning from urban design. Working with the aging Gottlieb to understand the nuances of scheduling, the Stephensons quickly discovered why this task had stumped so many. Crafting a schedule wasn’t just about crunching numbers – it was about juggling countless human considerations. “Many things about schedules are not quantifiable,” Henry realized, noting that a lot of judgment calls had to be made on the fly. Some NBA teams, for example, preferred more home games on weekends to boost attendance, even if it meant grueling travel for players, whereas others would sacrifice a prime weekend date to avoid a tough road trip. No algorithm in the ’70s could intuit those preferences.

So the couple changed tack. “Ultimately, we shifted our attention from trying to write a program that would generate whole schedules to becoming a scheduling service,” Henry explained. In other words, they let the computer handle the heavy lifting of generating draft schedules, but they would weave in the all-important human touch. They quit their day jobs – Holly left her position as a systems analyst and Henry his as a city planner – to focus entirely on this new venture. Before long, their mom-and-pop operation was up and running from the upstairs bedroom of their Staten Island home. They even landed a few early clients: the North American Soccer League hired them, and the National Basketball Association brought them on to compile its schedules for seven seasons. Holly found the work refreshing compared to typical corporate programming: “In the computer field, you tend to do fairly boring things… This is interesting because we follow through on the whole process – analyzing the system, doing the programming, working on the schedule and working with the people involved,” she said. In short, they got to solve a gigantic puzzle and see it come to life in arenas full of fans. “Then we get to go to the games at the end of the process and actually see our work,” Holly added, encapsulating the unique reward of their job.

Their big break in baseball came in 1981. MLB’s longtime schedule czar, Harry Simmons, was retiring after nearly 30 years of devising the league’s calendar (mostly by hand). The league needed a replacement who could handle an increasingly complex slate of games. By then, Henry and Holly had proven their mettle in other sports, and MLB hired the Stephensons to build the 1982 season schedule. The couple suddenly found themselves responsible for orchestrating one of the most complex annual undertakings in sports: 26 teams (at the time) playing 162 games each, all in sync without conflict. If the NBA had been a challenge, MLB was a behemoth. As one account later described, a normal MLB schedule is “an incredible act of calendrical harmony” – over 2,400 games spanning from spring to fall. The task was daunting, but the Stephensons were ready to tackle it together with their mix of computer savvy and common sense.

Masterminds of the MLB

From their Staten Island home office, the Stephensons set about choreographing baseball’s ballet of games year after year. The workspace itself was humble considering the magnitude of what it produced. The most prominent features in the room were two large tables – one holding their computer (state-of-the-art for its day) – and the walls were papered with National and American League schedules in progress. Nearby sat an even older computer, one that their two children, James and Katy, used for homework and that Henry and Holly had previously employed to map out the NBA slate. In this room, husband and wife would spend countless hours each winter sorting out the following year’s baseball calendar. The computer could spit out a basic draft schedule (and mercifully catch obvious impossibilities, like “three teams winding up in the same city at the same time,” but fine-tuning that draft was a four-month exercise in compromise and creativity. As Henry noted, “You’d be surprised how much has to be done by pencil” despite all the computing power. Holly agreed: “The computer does the easy part. It will put out a beautiful schedule, but it can’t compensate for problems like an arena not being available,” she said. In other words, the machine churned out raw material – it was up to the Stephensons to shape it into a workable final product.

What made scheduling so thorny? The variables were endless. For one, Major League Baseball was essentially two leagues (American and National) with different structures that had to be meshed together into one master timetable. Then there were the teams that shared cities or stadiums – the Mets and Yankees, Cubs and White Sox, Dodgers and Angels, A’s and Giants – who absolutely could not be home on the same day or the traffic and logistical nightmares would be epic. Some ballparks doubled as football stadiums, meaning the baseball schedule had to tiptoe around the NFL in the fall. The players’ union, meanwhile, had its own rules to ensure humane working conditions: no team should play more than 20 days in a row without a break, nor have too many off-days bunched together; if you played a night game in one city, you shouldn’t have to play a day game in a far-away city the very next afternoon; and teams traveling from the West Coast to the East Coast were entitled to a day off to adjust. “Real-world constraints throw curveballs at what you’re trying to do,” as one mathematician summed it up – the problem space of all possible schedules was astronomically large, so human judgment was needed to guide the process.

And that was just the starting point. Layered on top were a litany of special requests and odd traditions that the Stephensons strove to honor. “Added to all that are the specific requests of the individual teams,” Henry noted. For example, the Baltimore Orioles always asked to be on the road on Preakness Saturday in May, since Baltimore’s attention would be on the famous horse race that day. The Minnesota Twins similarly preferred to skip town on Minnesota’s fishing season opening day (when a good chunk of their fans would be in a boat with a rod and reel). The two Canadian clubs, Montreal and Toronto, hoped to be at home on their national holidays like Canada Day (July 1) or Victoria Day. Over in Boston, it was a cherished New England ritual that the Red Sox play a home game on Patriot’s Day each April, starting late in the morning so fans could watch the finish of the Boston Marathon and then head over to Fenway Park. And nearly every team clamored not to be stuck at home on days like Mother’s Day or Easter Sunday (tough draws for attendance) but would gladly host on Father’s Day or the Fourth of July, when crowds were plentiful. As Henry quipped to one reporter, “Every team wants to play the Yankees on the Fourth of July, and it’s just not possible.” Accommodating all these preferences without breaking the core scheduling rules was a yearly tightrope walk.

No matter how carefully the Stephensons tweaked and tuned the schedule, someone was always unhappy. They learned this lesson the hard way their very first season. The 1982 schedule they produced looked sensible on paper – until Mother Nature threw a nasty curveball. On Opening Day, April 5, 1982, Henry and Holly drove down from New York to Baltimore, proudly joining a crowd of 52,000 to watch the Orioles (a team they had placed at home) beat the Kansas City Royals. It was a chilly 46°F, but a thrilling moment for the couple: the first Major League game ever played on a schedule they had built. Their joy lasted barely 24 hours. The very next day, an unseasonable blizzard and cold snap hit the Northeast. Nearly a week’s worth of games that the schedule had slated in cities like New York, Boston, and Detroit were wiped out by snow and rain. Meanwhile, out in California, the Angels enjoyed mild weather, and in Seattle the Kingdome (with its roof) sat idle while other teams were rained out. The media and team executives lambasted the “stupid” schedule makers – how could the Stephensons not have foreseen this freak spring storm? Why on earth didn’t they start all the East Coast teams on the road out West, or ensure dome teams like Seattle were home in early April? Henry and Holly were stunned by the barrage of criticism. Chastened and determined not to be caught out again, they responded by crafting a “warm-weather” schedule for two years later: to start the 1985 season, they arranged for almost every team to open in either a warm southern city or under a dome, minimizing the risk of weather postponements. That fix created a whole new chorus of complaints. Western Division teams fumed that they had been forced to host Opening Day (which can be a harder sell to fans) just because of a one-time blizzard in the East. In trying to please those who had yelled the loudest, the Stephensons had irked others. It was a no-win scenario.

“Pleasing everyone, we quickly realized, was out of the question,” Henry said of their early baptism by fire. In fact, the only constant in their line of work was criticism. If a team had an especially brutal August road trip or not enough summer weekend home games, you could bet the schedule makers would hear about it. And yet, once in a while, fortune would smile and they’d get a rare bit of praise – or at least, the absence of blame. In 1982, by pure happenstance, the American League East title came down to a head-to-head clash in the final days of the season between the Milwaukee Brewers and Baltimore Orioles, two teams that just so happened to be scheduled to play each other in the last series. Suddenly Henry and Holly were hailed as geniuses for arranging such a dramatic finish. Henry laughed at the idea that they’d somehow predicted it: “I thought that happened every year,” he joked. More often, though, the Stephensons felt they “get far too much blame when things go wrong, and far too much credit when things go right.” Their goal was never to make a schedule that would draw applause, but simply one that was as fair and neutral as possible. “What you don’t want to do is stick one team with all the problems,” Henry explained. The main objective was to give everyone a level playing field, schedule-wise, even if that meant nobody would love the outcome. If no team was too aggrieved, it was a job well done.

Each year, the process followed a familiar rhythm. In December – a full 16 months before the season in question – the Stephensons would start gathering inputs for the next schedule. They sent every team a questionnaire: What did you dislike about last year’s schedule? Any special requests for next year? By spring, after rounds of computer runs and manual adjustments, a “basic draft” schedule would emerge, which Henry and Holly then spent months refining in consultation with league officials. Series matchups were often arranged in repeating patterns (e.g. Team A plays Team B in back-to-back weeks, once in each city) to make swaps easier if needed. By early summer – often by June – their part was essentially done. The league would circulate the draft to teams, who might tweak a game date here or there. TV networks would later chime in to set marquee game times. But the heavy lifting – deciding who played whom, where, and when, for 2,000+ games – was completed quietly by the Stephenson duo long before fans even finished enjoying the current season. Come December, when MLB officially released the schedule for the following year, the inevitable grumbling would begin anew. “Nobody’s ever satisfied with it,” shrugged one American League executive, comparing schedule makers to umpires – an indispensable part of the game, yet perpetually under fire.

The Partnership

Throughout this immense undertaking, Henry and Holly had one constant: each other. The pressures of sports scheduling might have driven some couples apart – imagine juggling thousands of constraints on a tight deadline, year after year, all from your home, with no one else to blame when things go awry. But the Stephensons turned it into a true partnership, each drawing on the other’s strengths. In the early years, they jokingly dubbed their operation a “mom-and-pop”shop, and it really was: the couple working long hours side by side, with kids wandering in after school doing homework on the spare computer. Rather than chaos, it created a kind of familial teamwork. Holly’s detail-oriented mind complemented Henry’s big-picture perspective; when one grew frustrated staring at an intractable scheduling snag, the other would take a crack at it, or offer a fresh angle. They made a point to break up the grind – often stepping away from the wall of charts and screens to discuss an issue over dinner in the next room, or taking a brief ferry ride into Manhattan for a change of scenery. And when the final schedule draft was done each year, they celebrated the accomplishment together, sometimes with a special night out or by planning a trip to see Opening Day of the season they’d just constructed.

“It’s a very interesting job,” Holly said, because it allowed them to see a massive project through together from start to finish. How many couples get to say they jointly authored the fate of an entire baseball season?

They shared the stress, but also the satisfaction. If one of them pulled a late-night eureka moment by finding a clever fix for a thorny travel problem, the other was the first to cheer. And if external criticisms sometimes stung, Henry and Holly could laugh it off privately – after all, who else could truly understand the crazy quirk of being professional schedule makers? It was often just the two of them in that upstairs office at 2 AM, poring over matchups and dates, keeping each other awake with coffee and humor. In a sense, every schedule was like a gigantic puzzle they solved as a team, and with each passing year their communication became more intuitive. “We follow through on the whole process… working with the people involved,” Holly had said about why she loved the job. The people involved were, first and foremost, the two of them. Together, they navigated MLB’s ever-evolving landscape – new teams, new divisions, interleague play – adjusting and learning in tandem. When the job demanded they relocate in the 1990s, the Stephensons moved to Martha’s Vineyard, Massachusetts, continuing their work from a new home base. Different scenery, same partnership: Henry and Holly against the scheduling gods.

Their teamwork didn’t go unnoticed. Within league circles they earned a reputation as a dynamic duo, “two math and computer whizzes who did it all with nothing but a pencil and a piece of paper” (a bit of embellishment – they did use computers – but the phrase captured how much of the burden fell on their human shoulders). And as much as the baseball schedule was a yearly source of debate, it was also a source of awe when people realized its complexity. In the pre-Internet era, many assumed the schedule was cranked out by some secret IBM mainframe buried in a mountain, or conversely, that it was so simple a couple of clerks could do it over a long lunch. “The truth lies somewhere in between,” Henry noted, chuckling at those two extreme. The Stephensons themselves became part of baseball lore – albeit quietly, behind the scenes. They were invited to league meetings, feted at a few All-Star Games, and even got to attend some dramatic World Series games together, knowing the road that led there was one they had paved. Those shared experiences only strengthened their marital camaraderie. Holly once reflected that one perk of the job was getting to go to the games and “actually see our work” in action. One can imagine the two of them sitting in the stands on a cool October night, watching a pivotal playoff game that, months ago, they had placed on the calendar, and squeezing each other’s hands in pride.

The End of an Era

By the early 2000s, the world of sports scheduling was catching up to the Stephensons. The computational puzzles that once required their personal touch were becoming the domain of advanced algorithms and university-backed operations research teams. The MLB schedule had only grown more complex – 30 teams by then, interleague games introduced, new ballparks with quirky availability issues – but computing power had also grown exponentially. In 2004, after 23 straight seasons of Stephenson-crafted schedules (1982 through 2004), Major League Baseball decided to open a new chapter. The league awarded the 2005 schedule contract to a tech-driven outfit called the Sports Scheduling Group, led by academic researchers and armed with sophisticated software. Henry and Holly, the consummate competitors, didn’t surrender easily; they immediately started working on a proposal to win the business back for 2006. “I’m a little surprised myself that we’ve been doing it this long,” Henry said in late 2004 as their streak came to an end, already gearing up for one more try. But the landscape had shifted for good. Computing algorithms proved they could avoid pesky quirks like back-to-back home-and-home series (those dreaded “semi-repeaters” that MLB wanted to eliminate) better than any human could. The era of the handcrafted baseball schedule was over.

The Stephensons retired from the scheduling game and settled into a quieter life. They remained on Martha’s Vineyard, that picturesque island off the Massachusetts coast, where they had a home full of memories – boxes of old schedules, dusty computer printouts, and perhaps a stray pencil or two left from late-night brainstorming. After spending so many years planning the future for baseball, Henry and Holly finally had time to plan their own days. Under normal circumstances, they might have filled their summer with visits from their children and grandchildren, enjoying the slower pace of retirement. But old habits die hard. In 2020, when the COVID-19 pandemic threw MLB’s carefully planned schedule into chaos, a reporter tracked down Henry (then 79) and Holly (74) to ask how they would rebuild the season if they were still in charge. Delighted by the mental challenge, the couple grabbed pencil and paper – of course – and sketched out an elegant solution in no time. “It’s seared in your brain,” laughed Henry about their scheduling instincts, comparing it to riding a bike. Even a decade and a half after their last official MLB schedule, the bond between them and the craft they mastered remained strong.

Henry and Holly Stephenson’s legacy lives on in every MLB season that unfolds without most fans giving a second thought to the planning behind it. They were the hidden conductors of baseball’s symphony of games, working in tandem to ensure that the show went on smoothly. In an upstairs room on Staten Island, they forged 25 years of calendars – and in doing so, forged a partnership uniquely their own. Their story has since been told in an ESPN documentary short aptly titled “The Schedule Makers.” It reveals how a married couple with a shared love of puzzles and problem-solving could tame a task that flummoxed corporate titans and computer giants, all while keeping their sense of humor intact. The rhythms of the baseball season – the ebbs and flows of road trips and homestands, the traditional dates fans mark on their calendars – owe a great deal to the Stephensons’ diligent work. And for Henry and Holly, those years of collaboration are a point of pride. They didn’t just balance the MLB schedule; they balanced each other. In the end, the most important lineup they ever coordinated was their own: a team of two, perfectly in sync, proving that even the toughest jobs are a little easier when you tackle them with someone you love.

Until next week…