How did 29 MLB teams pass on Orioles superstar Gunnar Henderson?

Gunnar Henderson, for about an hour, thought he was going to college.

It was June 3, 2019, the first day of that year’s Major League Baseball Draft, and Henderson — now a 22-year-old supernova shortstop for the Baltimore Orioles — was then a baby-faced teenager sweating through the biggest day of his young life. Unlike the class’ truly elite prospects, who were either on-site at the draft in New Jersey or had elaborate camera setups at home, Henderson’s draft party was a low-key affair. He took in the proceedings at the house of a coach, surrounded by about 20 family and friends.

Ahead of the draft, the high school infielder from Selma, Alabama, was a known commodity, highly touted and highly scouted. A string of strong performances in front of MLB scouts on the showcase circuit the summer before had solidified him as one of the more promising prep hitters in the class. Most major publications pegged Henderson somewhere toward the back half of the first round, between picks No. 14 and 37.

But that’s not how it went. As the picks flicked by, Henderson’s phone stayed silent.

Teams that had shown some level of pre-draft interest went in other directions. The Phillies took UNLV shortstop Bryson Stott at No. 14. Washington tabbed junior college pitcher Jackson Rutledge at 17. The Rays and Dodgers, at picks 22 and 25, had been rumored landing spots for Henderson, but they selected college infielders instead. With each name called, it became increasingly unlikely that a club would draft the sweet-swinging 17-year-old high enough to meet his bonus demands, reportedly around $2 million.

That’s when reality started to dawn on Henderson.

“As it got to the later half and the Astros — they were kind of hot on me — once they picked, I just kinda, like, told everybody: I’m gonna go to Auburn,” Henderson recounted to Yahoo Sports on a recent spring day at Camden Yards.

Then, out of nowhere, the Orioles called.

Henderson says Baltimore hadn’t contacted him or his agent before the draft. Such an approach is actually common practice for a number of teams, who use the tactic to retain leverage. For Henderson, it was a wonderful surprise.

Baltimore, which had already selected Oregon State catcher Adley Rutschman with the No. 1 pick, planned to surpass Henderson’s financial ask with a $2.3 million signing bonus. The doormat Orioles, coming off a franchise-worst 47-115 season, chose him with the 42nd overall pick, the first selection of the second round. It was later in the night than Henderson had hoped, but the bonus was sufficient for him to forgo his commitment to Auburn. Henderson would turn pro.

That decision looks excellent now.

Just five years later, Henderson is already one of the best players in baseball, a legitimate MVP candidate tearing MLB asunder. The reigning AL Rookie of the Year has thumped 19 home runs and compiled 4.2 bWAR in his first 60 games. Only Aaron Judge leads him in those categories. What’s more, Henderson, alongside draft-mate Rutschman, has become the face of a resurgent Orioles franchise likely to make the postseason in back-to-back years for the first time since the late 1990s.

Very few players in MLB history have ever been this good this young; Henderson is primed to become only the 23rd player age 23 or younger to be worth at least 8.0 bWAR in a single season in the Integration Era. Most of his company — Manny Machado, Bryce Harper, Ken Griffey Jr., Alex Rodriguez — were top-10 picks. Even Mike Trout, who famously fell to pick No. 25, was still a first-rounder.

Henderson, who won’t turn 23 until June 29, went 42nd overall.

Every team except Boston, which didn’t have a first-round pick that year, said thanks but no thanks to the shortstop. Some won’t lose a wink of sleep over it. The Royals and Yankees found their own franchise shortstops, Bobby Witt Jr. and Anthony Volpe, with picks No. 2 and No. 30. Corbin Carroll, sophomore slump aside, looks like a huge win for Arizona at pick No. 16. The Mariners uncovered a frontline starter at No. 20 with George Kirby.

But a handful of clubs, with the help of hindsight, would love a mulligan.

Today, the industry agrees that Baltimore, perhaps the league’s most adept organization at developing hitters, was the perfect place for Henderson to blossom. How the O’s, led by GM Mike Elias, molded a raw, talented swinger into an elite hitter deserves its own article. But developmental aptitude aside, scouting groups that passed on Henderson, according to conversations with a variety of front office personnel, had identified flaws with either the profile, the player or both.

The profile

High school hitters are an inherently risky demographic. The gap in quality between high school pitching and pro pitching is a canyon. That means prep bats either take longer to develop or never develop at all. Only one high school hitter taken between 2013 and 2018 and given a bonus over $2.5 million became a true star: Houston outfielder Kyle Tucker. Oft-injured Twins third baseman Royce Lewis might join him, if he can stay healthy.

That horrifying track record of high school hitters put some teams off Henderson immediately. The weak high school competition he faced in small-town Alabama made him an even more volatile proposition.

“No one has any clue what kind of approach/swing decisions a high school hitter is going to have in pro ball, and that’s, like, the majority of what determines whether they’ll hit or not,” one front office person explained in regard to Henderson and the industry attitude toward high school hitters as a whole. “Oh, cool, he didn’t chase the 77 mph fastball — noted.”

But beyond the fact of being a high school hitter, like any player, Henderson had nits worth picking, specific flaws that threatened to overshadow what he did so well: hit the baseball hard and far.

The player

The biggest question was about his defensive home. Teams were doubtful that Henderson, 6-foot-3 and broad-shouldered, would remain at shortstop as he continued growing. One team that passed on him had a scouting report that read: “Lacks true foot speed or instincts to stick at SS long term.”

A move down the defensive spectrum to either third base or the outfield would have put even more pressure on Henderson’s bat, and there was serious skepticism about whether he would make enough contact for his raw juice to shine. One team was particularly concerned about Henderson’s propensity to over-rotate while swinging, which made it exceedingly difficult for him to cover the outer half of the strike zone.

Hindsight is 20/20. Fast-forward to today, and Henderson has stayed lithe enough to remain at the infield’s premium position while making the swing adjustments necessary to do big damage on pitches all over the zone. But back in 2019, nobody thought improvements this significant would happen this quickly. Not even the Orioles had Henderson pegged as a future MVP candidate.

Conversations with a plethora of scouting personnel from a variety of organizations tell a simple story: Drafting is really, really hard. Trying to determine who will blossom and who will bust is a difficult endeavor. Each year, teams with good processes make bad mistakes. The success rate is getting better every year, as technology and information become more widely available, but one veteran scouting person described it as “weighing the dice to the best of our ability, but still throwing dice.”

That helps explain why Henderson went undrafted far longer than he or the industry expected. A handful of teams with track records of drafting and developing homegrown talent didn’t seriously have him on their radars. Other clubs that adored him simply weren’t sure he was worth the value. Each pick happens within its own particular context, with its own particular factors pulling the strings.

The what-ifs

The Phillies didn’t consider Henderson an option at No. 14 but loved him as a player and planned to meet his bonus demands if he fell to their next pick at 81. Stott, the player the Phillies selected in the first round, has become an every-day player and a key member of their core. Said a non-Phillies executive involved with another team’s draft: “I think almost every team would have taken Stott over Henderson. Maybe [Baltimore], too.”

But Washington, which picked three slots later, would probably love a redo. The team was interested enough in Henderson to invite him to Nationals Park for a pre-draft workout. But when the 17th pick rolled around, Henderson’s flaws spoke louder than his skills, and the Nats opted for Rutledge, a long-limbed hurler whose career has somewhat stalled in Triple-A. There’s still a chance Rutledge catches a second wind as a late-bloomer, but there’s no doubt that Henderson has become the superior player.

The Rays, who had three picks between 22 and 40, giving them sufficient financial leeway to sign Henderson had they wanted to, didn’t think he was sufficiently overpowering the competition like a first-rounder should. One individual involved with Tampa Bay’s draft admitted to Yahoo Sports that Henderson was a lot more talented than they appreciated but also emphasized that the O’s have done a stellar job with his development.

The Yankees, who nabbed Volpe at 30, never considered Henderson with that pick. They liked him, according to sources, but not enough to risk their top two selections both on high school hitters. With pick No. 38, New York instead opted for a left-handed pitcher from the University of Missouri named T.J. Sikkema, who has yet to reach the big leagues and is now pitching in the Reds organization.

Houston, which according to Henderson expressed significant pre-draft interest, chose college catcher Korey Lee with the 32nd pick. A high-placed scout in Houston’s draft room reportedly lobbied hard for Henderson but couldn’t convince the rest of the room to make the leap for a high school shortstop with swing questions and third-base risk.

Pittsburgh, which had picks at Nos. 18 and 37, is perhaps the team that came the closest to drafting Henderson. For the first of those two picks, the Pirates selected Quinn Priester, a prep pitcher who made his MLB debut last summer and looks like a solid rotation piece moving forward. But that second pick is the type of choice scouting directors lose sleep over.

The club, at the time, did not yet use a statistical model to help its draft room, as it does now. According to sources, the Pirates liked Henderson a lot, but like other teams, they were wary about his ability to stay up the middle. And so they instead selected a Philadelphia-area high schooler named Sammy Siani, who looked like a potential every-day centerfielder. Siani, still only 23, is enjoying something of a late-blooming breakout season with Pittsburgh’s Double-A affiliate but is still light-years behind the precocious Henderson.

And so, the Orioles were both lucky and good — fortunate that no other club pounced on Henderson and beneficiaries of their own due diligence. Despite their lack of contact with Henderson and his representatives ahead of the draft, Baltimore’s scouting department had done a thorough job on the Alabaman. The team’s scouts zeroed in on his rotational verve and quick-twitch athleticism, referring to him as an in-box monster. They also loved his make-up: his demeanor, work ethic and approach to the game. Henderson was, according to sources, much higher than 42nd overall on Baltimore’s draft board. The Orioles believed that if everything broke right, Henderson could become a very good, every-day third baseman.

The reality, then, has far surpassed even Baltimore’s wildest dreams. The best-case scenario came about 100 points of OPS ago. Nobody takes a player in the second round expecting a superstar.

But Henderson — along with the club’s player development group — had other plans.