Gregg Olson sees plenty of similarities between the Orioles’ 1989 and 2023 teams. He hopes they soon have another aspect in common.

For his contributions to the unexpected success of the 1989 “Why Not?” Orioles, Olson became the first reliever to win American League Rookie of the Year. No Oriole has received that honor since, but that likely changes Monday, when Baltimore infielder Gunnar Henderson is expected to win it. Every other AL team has had at least one Rookie of the Year since Olson’s win, with five clubs having four recipients in that span.

“It’s been way too long,” Olson told The Baltimore Sun. “Somebody else can take the mantle now.”

In Henderson, Olson sees a fitting successor. Amid a 1988 season that infamously began with a record 21 straight losses and ended with them holding the worst record in the majors, the Orioles drafted Olson fourth overall out of Auburn University. The next year, the 22-year-old right-hander with a devastating curveball had a 1.69 ERA and 27 saves in 64 appearances, receiving 26 of 28 first-place votes for AL Rookie of the Year. Future Hall of Fame outfielder Ken Griffey Jr. finished third.

Henderson, a Selma, Alabama, native, was also bound for Auburn before Baltimore selected him in the second round of the 2019 draft. That spring, Henderson’s older brother, Jackson, played at Auburn, and he roomed with Olson’s oldest son, Brett, on the Tigers’ road trips.

“It’s a really cool link,” Olson said.

But Olson sees more in common between Henderson and his own predecessor for the award among Orioles: Hall of Famer Cal Ripken Jr., the 1982 AL Rookie of the Year. Both tall infielders, Henderson and Ripken split their rookie seasons between shortstop and third base while hitting 28 home runs, a total that ties them for second among rookies in Orioles history.

“Same person, same work ethic, same type of player,” said Olson, who, like Ripken, has overcome a prostate cancer diagnosis. “Just seems to be a better person off the field than a player on the field.”

That’s high praise for Henderson, who has received plenty of it in his young career. The 22-year-old entered this season regarded almost unanimously as baseball’s top prospect. He overcame a slow start to become only the 13th rookie to win a Silver Slugger Award since the honor was introduced in 1980 to recognize offensive prowess at each position.

As Olson did in 1989 when Baltimore pushed for a playoff spot until the final series of the season, Henderson played a vital role on a young team that surpassed outside expectations, earning Most Valuable Oriole on a club that won 101 games and the AL East.

“A lot of these young guys really probably had no idea that they weren’t supposed to be doing what they were doing,” Olson said.

Having already received similar honors from the Major League Baseball Players Association, Sporting News and Baseball Digest, Henderson is positioned to be voted AL Rookie of the Year by the Baseball Writers’ Association of America. Since Olson won in 1989, the Orioles have had three players finish as runner-up: Rodrigo López in 2002, John Means in 2019 and Adley Rutschman in 2022.

When the announcement of Henderson’s win officially comes Monday night, Olson — a 57-year-old speaking from experience — believes it will change not only Henderson’s career but also his life. Olson went on to pitch for 12 more seasons, four of them with Baltimore as he became the franchise’s career saves leader and a member of its Hall of Fame, before a post-playing career in scouting and broadcasting.

But Olson happily feels defined by an honor he received 34 years ago.

“You just don’t understand what the ‘ROY’ means when you sign a ball,” Olson said. “It always stays with you. It’s like ‘HOF.’ Obviously not [to that same level], but it’s just one of those things that always goes with you everywhere you go and every time that you’re talked about.

“It’s like a stamp that goes with you for the rest of your life. I’m going to die and be remembered as the Rookie of the Year.”

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