TORONTO — The text Jared Halpert received from Jack Flaherty was so in character it could’ve been from a decade ago and his former coach wouldn’t have blinked an eye.

Flaherty had just been traded from the St. Louis Cardinals to the Baltimore Orioles, a move that sends the right-handed pitcher from a team far out of postseason contention to one that leads the American League. He’ll join a rotation that needs reinforcements for this stretch run toward October and beyond, and he’ll be one of the few pitchers with playoff experience.

“I can’t wait to win,” the text message read.

It’s the same thing Halpert saw early on from Flaherty at Harvard-Westlake School, where Flaherty followed in the footsteps of fellow first-round draft picks Max Fried and Lucas Giolito to become a force at the Los Angeles-area baseball powerhouse.

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Under then-head coach Matt LaCour, Flaherty grew from an all-America shortstop and third baseman into the next ace of Harvard-Westlake’s staff. In the biggest moments, it seemed to LaCour and Halpert that Flaherty reached a different intensity level — and a decade later, after experiencing a whirlwind of a trade deadline that resulted in him leaving the only organization he’s ever known, Flaherty feels that intensity swelling ahead of his first start Thursday against the Toronto Blue Jays.

In that one text to Halpert, Flaherty summarized his point of view entering life as an Oriole.

“I thought that was pretty telling what the O’s are going to get,” Halpert said. “Jack wants to win, man. I think that’s a driving force more than anything else.”

Flaherty echoed as much Wednesday afternoon. Standing in the bowels of Rogers Centre, having just arrived on a flight from St. Louis, Flaherty was all about the hunt — just as he always has been.

“It’s exciting to be on a good team,” Flaherty said. “It’s exciting to be on a team that’s in it.”

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Along with pitching prowess, Flaherty has athletic ability that once made him a hitting prospect. (Dilip Vishwanat/Getty Images)

‘He’s going to take the ball’

Back then, when Flaherty was a skinny freshman, LaCour was captivated by Flaherty’s athleticism in the field. Even now, he thinks Flaherty could have become a major league third baseman, but his arm talent took strides incrementally — and then all at once.

He was a sophomore when Fried and Giolito finished their Harvard-Westlake careers, and Flaherty soon stepped into the gaping hole left in the pitching staff without those first-round talents.

Flaherty developed his slider as a sophomore. He gained more velocity as a junior. And, while he still sat around 89 to 92 mph as a senior, the room for further growth in the minor leagues was apparent after a final Harvard-Westlake season in which he struck out 125 batters in 78 innings and pitched to an 0.63 ERA.

“We joked that Jack could probably throw with his eyes closed and probably throw 70% strikes,” said Halpert, who has risen from an assistant to become Harvard-Westlake’s head coach. “The drive Jack had, seeing Giolito and Fried, it certainly helped, but ‘determined’ is probably an understatement to make this happen.”

That drive — and the success that followed — became clear to Halpert during Flaherty’s junior year. In a matchup against Loyola High School, a local rival that featured several college commits, Halpert recalls Flaherty’s “defining moment”: a complete-game shutout that required no more than 80 pitches.

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In his final high school appearance, a postseason game against Riverside North, Flaherty spun a no-hitter.

“It was that kind of a stage where the pressure was certainly on. I think we probably felt it as more of a pressure situation than he did,” Halpert said. “Not only does this kid have the potential, but in the biggest moments here he’s going to take the ball and he’s going to end the game.”

Since those days at Harvard-Westlake, Flaherty has been on the radar of several decision-makers inside an Orioles front office that just completed its first trade deadline as buyers. General manager and Executive Vice President Mike Elias saw Flaherty as more of a position player while he was the scouting director for the Astros.

Matt Blood, however — who has since become Baltimore’s director of player development — was an area scout for the St. Louis Cardinals. He spent a summer watching Team USA’s U-18 team, and he quickly noticed what Flaherty could do on the mound at the Tournament of Stars in Cary, North Carolina. Later, inside the Dou Liou Stadium in Taiwan, Flaherty struck out nine batters and allowed two hits in six innings against Italy.

A year later, inside the Cardinals draft room, Blood heard the rave reviews from other scouts who had seen Flaherty, too.

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“He had a presence about him. He had some polish to him,” Blood said. “It’s like, this is what they look like, in terms of size and athleticism and poise.”

In the years since, Flaherty has lived up to the hopes that filled the St. Louis draft room in 2014. And now, for at least two months, he’ll try to live up to the new optimism around him in Baltimore.

Knowing what is expected

Each offseason, Flaherty returns to where it all began.

He throws his bullpen sessions at Harvard-Westlake, then picks up a bat and heads to the cages to lay down bunts for 30 minutes — just in case his team has a real need. Then comes his hour of pitcher’s fielding practice on a side field, employing one of the Harvard-Westlake assistants to throw mock grounders around the mound for him to chase.

The routine occupies his winter in Southern California. And, for the last nine years, all of that work was with the Cardinals in mind.

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Flaherty reached the majors in 2017 as a 21-year-old, and he became a mainstay in the organization with 196 1/3 regular-season innings and three postseason starts in 2019. Injuries have limited his usage in recent seasons, but Flaherty, healthy in 2023, is well on pace for another heavy innings load.

He’ll finish those innings with the Orioles, though, and in the clubhouse Wednesday he introduced himself to new teammates and tested out which new hat would fit best. For at least a little while, this will all feel weird.

“It’s about performing now,” Flaherty said.

That, at least, isn’t new.

“He’s a winner. He wants to win,” LaCour said. “Being in a winning environment is really important to him. He thrives in a winning environment, and you’re going to see an intensity in him that sometimes people are kind of turned off by it, but honestly, it’s what makes him tick. He gets into a zone. And when he gets into a good zone, there aren’t a lot of pitchers out there who are better than him.”

The beginning of Flaherty’s season was uneven, and his ERA ballooned to a high of 6.29 in May. Much of that, Flaherty said, was down to his fastball command. One issue led to the next, but they gave way to a strong July in which he allowed three runs or fewer in four of his five starts.

And, as a new member of the Orioles, Flaherty knows what is expected of him. There’s pressure involved with being a winning team’s major trade acquisition. There’s also excitement, though, that can be abridged to a text message to a high school coach who has seen Flaherty play his best in these situations.

He can’t wait to win.

Andy Kostka is an Orioles beat writer for The Baltimore Banner. He previously covered the Orioles for The Baltimore Sun. Kostka graduated from the University of Maryland and grew up in Rockville.

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