On the evening of June 3, 2019, roughly 50 people gathered in the backyard of a single-family home in Valley Grande, Ala. The sun was still high on a 92-degree day that showed no signs of cooling down as the group stood around the pool, munching on chips, dip and pizza.

Kerry and Allen Henderson had been hesitant about attending the party. Hosted by a friend, it was a watch party for Major League Baseball’s annual draft, and their 17-year-old son, Gunnar, was among those hoping to be selected. They were anxious, and wondered if they should have just watched at home. But the host, Terry Waters, had thrown batting practice to Gunnar for MLB scouts who came to their small neighboring town, Selma, which has roughly 16,000 people. Waters and many others in the area felt invested in the outcome of the draft.

Gunnar was a consensus first-round pick, a powerful 6-foot-3, 195-pound shortstop at John T. Morgan Academy, who had been named Alabama’s top high school basketball player. Mock drafts had him going between picks 14 and 25. Pick No. 25 was “the floor,” per The Athletic’s draft expert Keith Law.

The party was in full swing as the first 10 picks flashed on a big flat screen showing the MLB Network’s live broadcast. Then people began to pay closer attention. The Phillies, who told Henderson they would take him at No. 14 if college shortstop Bryson Stott wasn’t available, got their top choice. Three picks later, the Nationals, who had hosted a private workout for Henderson, went with pitcher Jackson Rutledge. The Dodgers used pick No. 25 on Tulane third baseman Kody Hoese.

The names kept ticking off. The group kept waiting. The Yankees had always preferred another high school shortstop, Anthony Volpe, and took him – the eighth shortstop drafted – at No. 30. A faction of Houston’s scouting department wanted Henderson, but the Astros ultimately selected Cal catcher Korey Lee with pick No. 32.

Every team but Boston, which didn’t have a first-round pick that year, passed on Henderson. The Pirates passed on him twice, as did the Dodgers. Arizona and Tampa Bay passed on him three times each. The athleticism was enticing, as were Henderson’s raw tools, but he wasn’t a sure bet. He hadn’t fared that well on the recent summer circuit. The Astros weren’t sure he could make enough contact and stick at shortstop, and the Dodgers had concerns about his swing and lack of domination against the weaker competition Henderson faced in Selma. Team after team didn’t want to take the risk.

When the Texas Rangers took Baylor third baseman David Wendzel with pick No. 41, the broadcast of the draft ended — only the first round and nine compensatory/competitive balance picks were televised — and the TV was switched to another channel.

A pall fell over the party. Kerry fought back tears. Allen felt sick. Eventually, Gunnar and his parents tried to lighten the mood, reminding everyone of the fallback plan.

“We’re going to Auburn!” the trio announced. The group cheered.

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Gunnar Henderson never made it to Auburn.

The 23-year-old is one of the top five players in Major League Baseball, by FanGraphs WAR. He’s the reigning American League Rookie of the Year, an All-Star and the face of the Baltimore Orioles, a team widely regarded as being in the early phases of a potential dynasty. The O’s will begin the wild-card round of the playoffs against the Kansas City Royals on Tuesday, and their shortstop — coming off one of the best single seasons in Orioles history — will take center stage.

Henderson was drafted with the first pick in the second round and is one of the bigger scouting misses in recent memory. Most of the prospects drafted before Henderson are still in the minors, or struggling to prove they belong in the big leagues. Only No. 2 pick Bobby Witt Jr. of the Royals has been as impactful a hitter.

“Every city we go to, you talk to other coaches who are like ‘How did this guy last that long?” said Orioles manager Brandon Hyde.

Henderson’s rise highlights the imperfect nature of the draft, as teams repeatedly talked themselves out of a talented but risky high school player. It’s also a developmental success story, as the plan Baltimore crafted for Henderson, including an unorthodox approach during the pandemic, set him up to arrive and produce in the majors earlier than expected.

In 2018, when Mike Elias was the Astros’ scouting director, he began scrutinizing the following year’s draft class, circling Henderson’s name as his preferred choice with Houston’s late first-round pick. But that November, Elias was hired as Baltimore’s general manager. The rebuilding Orioles had the No. 1 pick and would take Oregon State catcher Adley Rutschman.

On Baltimore’s internal draft board, Henderson, who was also well liked by the incumbent scouting group, was somewhere between Nos. 14 and 16. But because the Orioles wouldn’t pick again until No. 42, landing him seemed like a pipe dream. So much so that Kerry told her youngest son, Cade, to change out of the pajama pants featuring his favorite team — the Orioles — before he could go to the draft party.

As the draft picks got to the low 30s, and with Henderson’s name still out there, Elias — who had scouted Henderson more than two dozen times — called Henderson’s then-agent, Larry Reynolds, to ask: Would Henderson sign if they paid him over slot value? Reynolds wasn’t sure. The family had been pretty clear it was the first round or Auburn. They patched in Allen, who was still lingering at the Waters’ home. After the Auburn announcement, Kerry had gone to try to eat something. Gunnar was out back playing cornhole. There wasn’t time to gather them and relay the message, let alone make a life-altering decision.

A few minutes later, Gunnar and Kerry found out the Orioles had selected him in the second round on a ticker scrolling across the bottom of the TV.

No one slept that night. Kerry was up crying, tossing and turning and praying. She never cared which team took Gunnar or how much money he got. Instead she had hoped and prayed for a “clear path.” For her and Allen, being a first-round pick felt like a clear enough path for their son to bypass college. But now what?

The next morning, taking a walk through the neighborhood to think, Kerry received a call from Astros scout Travis Coleman, who had coached Gunnar in travel ball. “Baltimore doesn’t have a shortstop. There’s a clear path for him there,” Coleman said.

Elias called later that day, telling the Hendersons how excited he was that the Orioles had drafted Gunnar. He also mentioned that the Orioles didn’t have long-term infielders and that the organization was rebuilding around its young players. Baltimore, Elias said, was where Gunnar was supposed to be. “There’s a clear path here,” Elias said.

There it was again. Two people using the exact phrase Kerry had used herself to describe what she wanted for her son, that sealed it. Henderson agreed to sign with the Orioles for $2.3 million, $500,000 above slot value, forgoing Auburn.

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Within baseball, the COVID-19 pandemic has widely been considered a lost developmental year. The 2020 minor league season was canceled, with most players left to train on their own or not at all. The only setup allowed for Major League teams was an “alternate site” with a maximum of 30 players, which for most teams consisted of big leaguers and Triple-A players who could serve as roster depth for the big-league squad, covering injuries and underperformance.

Baltimore, fresh off a 54-108 season, sent Rutschman and Henderson to their alternate site, even though both were years away from being on a big-league roster. The thinking was simple: These were formative years, and they had just paid both guys big bonuses. What else were they going to do?

“It’s like you have a kid, and you have a choice of either he doesn’t go to school or you skip six grades,” Elias said. “We decided to skip six grades.”

Rutschman, an older, more polished college athlete who had gone through three levels his first pro season, held his own right away. Henderson, who had only 29 rookie ball games under his belt, struggled mightily. In his first at-bat, he faced Eric Hanhold, a journeyman reliever almost eight years his senior. He struck out on three pitches.

“He saw right away that Adley was having some success and he wasn’t good enough. And it drove him crazy,” said Orioles hitting coach Ryan Fuller.

Henderson had always been a tireless worker. When his parents came to visit him in rookie ball, he and Allen snuck onto a high school field after a bad game so Gunnar could swing out some of his frustration. There was no screen to shield Allen, so he held an old chain link fence in front of him with one hand and pitched with the other.

At the alternate site, Henderson “came to us right away and said, ‘I stink, let’s get to work,’” Fuller said. The focal point early on was the barrel entry on Henderson’s bat. It was too steep and he would pull his hands into the zone off plane. Even in rookie ball, Henderson had seen how exposed the natural loft in his swing left him to rising fastballs. So, for weeks, he worked in the batting cage trying to connect with little foam balls — “hoppy heaters” — that would rise as they approached the plate.

Each day, Henderson would get to the field around 10:30 a.m. and work in the cage. Then he’d take ground balls and roughly 5-10 live at-bats, totally overmatched against guys who had been in Triple A or the big leagues.

“Every single day he would take his beating,” said Matt Blood, then director of player development, “and he would go back to the cage and they would just train, train, train.”

There was nowhere to go but the hotel and the field, yet Henderson was in heaven. “It was probably one of the most fun times I’ve had playing,” he said. “It was all about development, and I took it seriously.”

There was no worrying about slash lines, or wins and losses. There were no distractions. “It was unlimited reps, and maybe we weren’t the smartest at the time, but we had young, motivated players wanting to hit,” Fuller said. “When we had downtime, we would go to the cage. And it wasn’t feel-good swings, it was always something really challenging. It was almost experimental at that point. But these guys knew that we were building for something bigger.”

Roughly three weeks in, Henderson started holding his own during the simulated games. A swing change that might have taken months or even a year under normal circumstances evolved much faster thanks to thousands of reps at the alternate site. Henderson was flattening out his swing to create a better path to the ball. The Orioles kept internal stats at the alternate site, and while Henderson’s batting average never recovered from the early shellacking, his OPS started creeping up, approaching the respectable .700s when it was through.

“This young dude is competing against these guys that he really had no business competing against,” Blood said. “And by the end of it, we’re all looking at each other like, if he keeps this rate of practice and development up, we might have an animal on our hands.”

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That fall, Henderson played in the Orioles instructional league. In 2021 Henderson started putting up what Elias calls “freakish exit velocity numbers,” and flew through three levels to end at Double A. By the following June, he was promoted to Triple A. There, Henderson slugged .504 with a .374 batting average on balls in play. He was promoted to the big-leagues on Aug. 31. Henderson’s first hit was a home run where he swung so hard — 107.1 mph off his bat — that his helmet fell off.

In spring training 2023, Henderson texted his now-fiancée, Katherine Lee Bishop, who is in her final year of pharmacy school at Auburn, his goal was to win AL Rookie of the Year. Before each season, he texts Bishop his big goal for the year, and then they don’t talk about it again.

In that 2023 rookie season, Henderson started slowly. Then on June 8, he hit a go-ahead, two-run, eighth-inning homer down the left-field line in Milwaukee that helped get his mojo back. Every night, he was showcasing the rapid improvements he’d made at the plate and a glove that could hold its own at shortstop. He did win Rookie of the Year, the first Oriole in 34 years to do so, and he did it in unanimous fashion.

This year, Henderson slashed .282/.366/.531 in 158 games. He had 92 RBI, 118 runs scored (sixth-most in baseball) and was voted Most Valuable Oriole for the second season in a row.  Still, after some games, Henderson bemoans to Bishop that he didn’t barrel up a ball all night. It doesn’t matter if he went 3-for-4 with multiple RBIs. In Triple A, Henderson would go from a full sprint to a full-stop down the first baseline so quickly that his manager Buck Britton had to look away, he was so worried about the young star blowing out a hamstring. It was Henderson’s way of blowing off steam.

“I wish he wouldn’t be so hard on himself sometimes,” Hyde said. “He literally doesn’t think he should ever get out … He will come back (to the dugout) and there’s sort of a bewilderment, like, how did that just happen?”

On a young Baltimore team, Henderson’s intensity is mixed with youthful exuberance.

For the All-Star game, Henderson had a Scooby Doo bat made and, when coming off the field, grabbed the ESPN mic to yell the cartoon dog’s signature line, “Ruh Roh Raggy!” Henderson also lists much-maligned Star Wars character Jar-Jar Binks as another top impression and is a surprisingly confident singer, thinking nothing of cranking up the radio and serenading Bishop on their first date.

“We have a couple of karaoke days on the (Orioles) bus,” said Henderson, who used Motley Crue’s “Kickstart my Heart” as his walkup song in the minors and then switch to Gwen Stefani’s “Sweep Escape” — an idea from his older brother, Jackson — to get the fans more involved. Henderson has an old country song he plays in the batting cages on Sundays, but teammates “never wanted me to sing it in there,” he said. He usually respects that.

Henderson’s manners are impeccable, if not jarring in a big league clubhouse. He  peppers every sentence with “sir” or “ma’am”, something coaches have had to tell him to stop doing. It occasionally still slips into an in-game conversation with Hyde. “We are past that now,” Fuller says, laughing. “No more ‘sir.’”

It’s a reminder of the way he was raised. When Henderson went pro, he promised his parents he’d get a college degree. Kerry and Allen have the notepad he scrawled it in for safekeeping. Henderson has completed enough online credits through Wallace Community College Selma, where Kerry works, to be a sophomore.  He’s working toward a Bachelor of Science in Business Administration, a goal that’s on hold now as he deals with more pressing matters.

Baltimore, whose last World Series win was in 1983, was swept out of the AL Division Series by the Rangers last year, ending a magical 101-win season. It was a setback chalked up, in part, to the team’s youth. The O’s, many national pundits believe, are just at the beginning of what could be a long run of success. This year, the expectations are much higher.

And while the Orioles have relied on key trades (like pitcher Corbin Burnes) and feel-good stories (Ryan O’Hearn and starter Albert Suárez), the roster is built around a young position-player core that includes Henderson, Rutschman, Jackson Holliday, Colton Cowser and Jordan Westburg.

All of those guys were picked higher in their respective draft classes than Henderson, who virtually any other team could have had. Instead, he’s in Baltimore, where his face is plastered on posters and where he has already passed a guy named Cal Ripken, Jr. for most home runs (37) by a shortstop in team history.

The awkwardness of that draft party five years ago feels light years away from an already-impressive career still in its infancy.

“The Orioles weren’t on my radar,” Henderson said, “but it worked out.”

(Top image: Meech Robinson / The Athletic; Photos: Scott Taetsch / Getty Images)

CHICAGO — A mere mention of the year 1991 elicited a pained groan from Sandy Alomar Jr. as he leaned against a railing in the Cleveland Guardians’ dugout.

Three decades have passed. Alomar played for seven teams across 20 seasons, appeared in 49 playoff games, won an All-Star Game MVP award and supplied a slew of unforgettable moments in a big-league uniform. He has coached for a consistent contender in Cleveland for 15 years.

And yet, he still can’t shake memories of that miserable ’91 season. That’s what losing can do — not the sort of losing that leaves players, coaches and fanbases disgruntled, but the degree of losing that beats the soul out of someone who can’t escape it.

“It hits you in the face every day,” said Cleveland pitcher Alex Cobb, a member of the 115-loss Baltimore Orioles of 2018. “Wake up, do it again. Wake up, do it again.”

Scanning the dugout of the historically inept Chicago White Sox during an early-September series at a mostly empty Guaranteed Rate Field triggered some flashbacks for Cobb.

He signed with the Orioles in late March 2018 and played catch-up for much of the year. By the time Cobb felt like himself, the Orioles were 40 games out of first place and he still had another dozen starts to make. He focused on sharpening his mechanics for the next season.

“You’re just trying to get through the day,” Cobb said. “You find ways.”

Of course, no one’s going to pity a big-leaguer who earns a seven-figure salary, enjoys ample leg room on charter flights, gorges on infinite servings of red meat at Brazilian steakhouses on road trip off days and throws a ball around for a couple of hours every five days.

“I don’t recall anyone feeling sorry for us,” said Orioles outfielder Cedric Mullins, who blossomed in 2021, when Baltimore lost 110 games. “In fact, it felt like it was blood in the water at that point.”

Still, it takes a mental toll on those completing nine fruitless innings night after night. No one knows it better than the White Sox, who broke the 1962 New York Mets’ record of 120 losses on Friday. Chicago was eliminated from playoff contention in mid-August. They sit more than 40 games out of fourth place in their division, a situation so bleak it’d test anyone’s drive.

“It’s definitely challenging to stay locked in and motivated,” said Ryan O’Hearn, a member of a pair of Royals teams that lost more than 100 games.

In 2021, Mullins became the first player since the franchise moved to Baltimore in 1954 to tally 30 homers and 30 stolen bases in a season. But he admits “it just wasn’t as fun” because the team was dreadful. His production dipped over the past three seasons, but he said he has enjoyed the experiences more.

“It’s funny,” he said, “when we go through stints like (the club’s recent funk), it feels like we’re losing. And I’m like, ‘You all have no idea.’”

When Torey Lovullo steered the Arizona Diamondbacks through a 52-110 season in 2021, his 25-minute commutes home from Chase Field were “dark.” He would sing along to Supertramp or Led Zeppelin to decompress and distract himself from whatever daunting matchup awaited his club the following day.

“I tried to go home and just be present at home,” Lovullo said, “and that became harder and harder throughout the course of the season.”

Several players said they would linger at home longer before heading to the ballpark, preferring not to spend an extra nanosecond in the monotonous misery.

“It can feel like a project to get to the stadium itself,” said Cincinnati Reds reliever Buck Farmer.

Farmer led the 2019 Detroit Tigers in appearances, with 73. The Tigers were 29-44 when he pitched and 18-70 when he didn’t.

“We lost a lot,” he said. “In my entire tenure there, we lost a lot.”

One hundred and fourteen games in 2019, to be precise. Enough to draw comparisons to the 2003 Tigers, who rallied during the final week of the season to avoid joining the ’62 Mets in the pantheon of futility.

“September was really hard,” said Matthew Boyd, who made a team-high 32 starts for the 2019 Tigers.

Both ex-Tigers pitchers, however, agreed there’s not much difference between 114 losses and, say, 98, the number of games Detroit dropped the previous two years.

“It’s all hard,” Boyd said.

“Either way sucks,” Farmer said. “Either way you draw it up, not having a winning season is tough. It sucks to lose.”

The clubhouse culture “can dictate how much that sucks,” Farmer said. In 2019, for instance, “it was like showing up for a 9-to-5, which sucks.” Sensing a theme here, or at least noticing a particular word that encapsulates the effects of perpetual losing on the psyche?

“It could have been a lot better,” said catcher Jake Rogers, another member of the 2019 Tigers. “It’s like the (2024) White Sox. You get to a point where everyone is like, ‘We’ve lost how many?’ That part sucks sometimes, but we weren’t thinking that (in) the moment. But you look back at it and it’s like, ‘Man, 114 is a lot.’”

In 2022, the Reds started the season 3-22, but Farmer insists no one would know based on the energy in the clubhouse. That can depend on the composition of the roster. When winning proves impractical, team goals tend to slip down players’ priority lists.

“I will never be OK with losing,” said Los Angeles Dodgers infielder Miguel Rojas.

Late in the Miami Marlins’ march to 105 losses in 2019, the players held a meeting after a series in Arizona. Rojas asked his teammates “to look themselves in the mirror and look up (other) rosters (to determine) how many more teams you could play for today,” a method of motivation he said he was taught when he broke into the big leagues.

“Being eliminated a month before the season’s over,” Rojas said, “it’s hard, because the fans feed off that, too. … It’s really hard to ask people to come to the ballpark. So it’s really hard to come to the ballpark every day. It’s really low-energy. You’re finding your own motivation to play the game. But you have to be professional. You have to show up every single day because you’re getting paid.”

“Everybody’s in a certain spot in their career,” Cobb said. “If you’re going to arbitration, you’re trying to fluff as many numbers or trying to prevent bad numbers from happening. If you’re older, you’re on a contract, you’re probably just trying not to get hurt, trying to work on stuff for the next year.”

And if you’re new to the major leagues?

“On a team like that, there are a lot of guys who are super excited to be here,” Cobb said. “You don’t get to ruin that for anyone. You don’t get to take other peoples’ joy away from being in the locker room.”

As the 2018 trade deadline approached, the Orioles dealt away Manny Machado, Zack Britton, Kevin Gausman, Darren O’Day, Jonathan Schoop and Brad Brach. In the second half, Cobb looked around the room and wondered who everyone was. He said the influx of young players ultimately “helped the mood.”

That youthful exuberance can help to dispel feelings of nihilism. As Cobb described, “You’re putting the X over the days on the calendar, just trying to get through it.”

“It’s hard to find those bright spots,” Mullins said. “And those bright spots aren’t going to be looked at too often, just because (of) the team. You want to see the team perform. Individuals can’t do that on their own.”

Outfielder Austin Hays, like Mullins, broke out for the Orioles in 2021.

“You really have to dig into why you’re playing when you’re down 8-0 in the third inning,” said Hays, who credited the birth of his son for giving him proper perspective.

During a 102-loss season with the Oakland Athletics in 2022, catcher Stephen Vogt — now the Guardians’ manager — would encourage veteran players to be “an extension of the coaching staff,” said pitcher Cole Irvin. Vogt would engage the team’s young players about pitchers’ tendencies or reading hitters’ swings.

The most reassuring reminder Vogt provided?

“You’re what the 12-year-old version of yourself wanted to be,” Irvin said.

That 12-year-old self couldn’t wait to get to the field, no matter the team’s results of the previous day or week or month.

“It’s really hard,” Boyd said, “but it’s a balancing act. You have to have awareness. You’re going to fall out of line, and when you do, you have to give yourself grace to gently get back in.”

Those trudges to the finish line can be scarring, though.

As Alomar shook his head, reflecting on that 105-loss Cleveland season in 1991, his former teammate, Carlos Baerga, approached. Alomar stopped him and mentioned the infamous year. Baerga shouted like he was suffering from appendicitis and then recalled the most valuable bit of advice he received in his career. Hitting instructor Jose Morales told him: “Don’t get used to losing, because when you get used to losing, you get lazy.”

Alomar and Baerga came up together with the Padres and won minor-league championships in two of their final three years in the farm system. Then they were shipped to Cleveland, where the Indians lost so much they became a baseball punchline and played in front of small gatherings in a cavernous dungeon on the shores of Lake Erie.

They never sunk lower than in 1991. Cleveland went four decades without a playoff appearance after a trip to the World Series in 1954, but no iteration of the Indians lost more than that ’91 team did.

Alomar tore his groin partially off his pubic bone, which ended his season in late July when the club was sitting at 33-63. He still showed up to the ballpark every day, like a wounded animal slogging toward the slaughterhouse. All he needed to see in the opposing dugout were a few veteran players, and he knew.

“They’re probably gonna kick our butt,” Alomar said.

— The Athletic’s Sam Blum, Chad Jennings, C. Trent Rosecrans and Cody Stavenhagen contributed to this reporting.

(Top illustration: Meech Robinson / The Athletic; Photo of Torey Lovullo: Steph Chambers / Getty Images; Alex Cobb: Rick Madonik / Toronto Star via Getty Images; Luis Robert Jr.: Thearon W. Henderson / Getty Images; Sandy Alomar Jr.: Focus on Sport / Getty Images; Miguel Rojas: Mitchell Layton / Getty Images)