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From Markakis to Wieters to Westburg: The longest-tenured Orioles scout keeps getting big picks from the talent-rich Southeast

David Jennings wasn’t a greenhorn when he joined the Orioles as a Southeast area scout, but it was only after diving into the job that he learned the scope of his new assignment.

He had been scouting for nearly a decade when the Orioles plucked him from the Cincinnati Reds and offered him the opportunity to move back home to Alabama and scout the surrounding states, and his coverage area for his first season in 2001 included a dozen first-day picks.

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“Is it going to be like this every year?” he asked himself, and even though it hasn’t been, he’s scouted everyone worth seeing in one of the most talent-rich areas in the country for the Orioles for 20 drafts since.

Now, the man who brought stars like Nick Markakis and Matt Wieters into the organization is the longest-tenured Orioles scout in an area where every spot on the map is liable to produce a talented young ballplayer.

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“You really appreciate when you have a longtime professional area scout that knows his area, knows the kids, has had the ups and downs up a scouting career and has that experience to tap into,” Orioles executive vice president and general manager Mike Elias said. “He’s very rock-solid in those areas.

“It’s a huge area, and the fact it has the SEC makes it highly action-packed every year. We like the baseball in that conference, so he’s always right in the thick of things and I think he is again this year.”

Jennings, 54, was a scout that Elias, a former scout himself, inherited when he took over in November 2019. He’s not the first to decide Jennings is worth keeping around; he’s worked for four different heads of baseball operations with the Orioles, with four different people in charge of the draft. All have trusted Jennings with big picks, Elias included.

Jennings’ brother, Dan, was already a scout rising up the ranks on his way to eventually being the Miami Marlins’ general manager when Julian Mock called to ask whether he wanted to get into scouting himself. Jennings was finishing up school and was based in St. Louis for the Reds until the Orioles gave him a chance to move back to Alabama in 2000.

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Orioles scout David Jennings is the longest-tenured area scout in the organization and has been the scout who signed four first-round picks in his 20 years with the club: Adam Loewen, Nick Markakis, Matt Wieters, and Kevin Gausman. In recent drafts, the Orioles have relied on him for opinions on top infield prospects Gunnar Henderson and Jordan Westburg.
Orioles scout David Jennings is the longest-tenured area scout in the organization and has been the scout who signed four first-round picks in his 20 years with the club: Adam Loewen, Nick Markakis, Matt Wieters, and Kevin Gausman. In recent drafts, the Orioles have relied on him for opinions on top infield prospects Gunnar Henderson and Jordan Westburg. (Tina Jennings/Tina Jennings)

Since then, he’s filled his resume with first-round picks, including Adam Loewen (2002), Markakis (2003) and Wieters (2007). In 2012 he added Kevin Gausman to that list, and when he was up with the Orioles along with Wieters and Markakis, Jennings was named the club’s Jim Russo Scout of the Year.

More recently, he signed four picks in the 2019 MLB draft, including top infield prospect Gunnar Henderson (42nd overall), third-round outfielder Zach Watson, and late-round right-handers Garrett Farmer and Houston Roth.

Half of the six-man 2020 draft class came from his coverage area as well, with No. 30 overall pick Jordan Westburg, second-round outfielder Hudson Haskin, and third-round shortstop Anthony Servideo.

While the 2020 class was a unique experience with limited in-person scouting, the 2019 group shows all the ways an entrenched scout can be valuable. Jennings had followed Henderson for years, watching him at showcases and at the John T. Morgan Academy in Selma, Alabama, when the whole town came out for playoff games. He did that under the assumption that Henderson, a first-round talent, wouldn’t be available when the Orioles picked at No. 42 that year.

He was, though, and the Orioles had all the information they needed from Jennings when that draft-day surprise fell into their laps. With Watson, Jennings had scouted him in high school as well.

Brad Ciolek, the Orioles’ domestic scouting supervisor, said Jennings doesn’t require much oversight and reliably covers that talent-rich area while being “very dependable, very approachable, very easygoing.”

“I think what’s really refreshing about DJ and how he goes about it is he’s definitely not a fence-sitter,” Ciolek said. “I’m not saying other guys are, but basically, if he has conviction on a player like he did Westburg, like he did Haskin, like he did Servideo, he’s just going to go out and tell you exactly where he likes him, where he thinks they should go, what they should do, what holes he can poke in certain guys. The bottom line is whatever he’s going to tell you, he has conviction in his opinion and he’s done the work and he feels comfortable, essentially, saying a round and value for that certain player.”

That has carried Jennings through several different Orioles regimes. There are changes every time, but none drastic, he said. Jennings allowed that this front office has brought “some changes now with the analytical side of it,” but that “everybody has come in and just let us do what we do, and that’s just scout — go see players.”

Orioles longtime scout David Jennings had followed Gunnar Henderson, pictured waiting for a pitch during a game with the IronBirds on June 22, for years, watching him at showcases and at the John T. Morgan Academy in Selma, Alabama, when the whole town came out for playoff games. He did that under the assumption that Henderson, a first-round talent, wouldn’t be available when the Orioles picked at No. 42 in 2019.
Orioles longtime scout David Jennings had followed Gunnar Henderson, pictured waiting for a pitch during a game with the IronBirds on June 22, for years, watching him at showcases and at the John T. Morgan Academy in Selma, Alabama, when the whole town came out for playoff games. He did that under the assumption that Henderson, a first-round talent, wouldn’t be available when the Orioles picked at No. 42 in 2019. (Matt Button / The Aegis/Baltimore Sun Media)

With so much quantifiable by the mountains of data even the amateur game produces now, a scout’s intuition on a player’s makeup is more valuable than ever. Jennings loves how the SEC produces high-intensity situations against top competition week-in and week-out.

“You get to see more of how they react in situations, just more of their feeling, how they’re fitting in in the games, how they can handle that kind of pressure,” Jennings said. “I think that’s a big part of it.”

Spending so long with the Orioles has made the benchmark for what will make a good pick very clear.

“The makeup and the character of the kid pretty much determines everything for me,” Jennings said. “Can he handle it? Is he ready for this? Can he beat the Yankees and the Red Sox? That’s one of the things I’ve always thought about when I go in and look at a kid. Is this guy going to put us over the hump?”

The Orioles have been asking that question for decades, and Jennings’ picks helped build the last team that could. He did so while raising a family with his wife, Tina, and tried his best to balance both.

When he could, especially when his sons Trevor and Dylan were younger, Jennings would use the pro coverage that followed the draft each summer to bring his family along. There were days spent whitewater rafting or zip lining in Gatlinburg, Tennessee, during the day, then ballgames at night. In Florida, they’d go to Disney World.

“You miss enough during the season that any quality time you can get is well worth it,” Jennings said.

Especially in an industry where jobs like his are disappearing, Jennings is grateful for his role with the Orioles. The team let go of four amateur scouts after the 2019 draft, and several organizations have more severely downsized their scouting departments in recent years.

The pandemic made that worse in some places, and Jennings’ wife took a second job last year out of fear that the Orioles would be one of those places. Scouts all over the league were let go or took pay cuts, but Jennings said the Orioles took care of theirs. That demonstration of value only enhances what he feels has been a dream career in the game.

“It’s been a fun life, for sure, scouting life,” Jennings said. “I guess it’s been 30 years now that I’ve been in it, and it’s afforded me a lot. It’s been fun.”

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