The bold move that led Gunnar Henderson to Orioles stardom: ‘We decided to skip six grades’

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.

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.

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.”

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)