Breaking: Jackson Holliday profile gives Orioles every reason not to fall for a classic Dylan Cease trap

Jackson Holliday, Baltimore Orioles

The Baltimore Orioles are in the Danger Zone. Another early postseason exit has folks seriously doubting the ceiling of this team, even as baseball’s deepest young core ages into its collective prime.

Mike Elias has done shockingly little to built out his roster. There was supposed to be a tangible shift in identity and approach under new ownership.

The O’s avoided big free agency spending for years under the Angelos. David Rubenstein sold fans on a grand vision of the future, but I’m not sure signing Tyler O’Neill to a three-year, $49.5 million contract qualifies as “going for it.”

Baltimore’s most glaring weakness remains the pitching staff. After trading for Corbin Burnes and benefitting from another brilliant season from MLB’s most consistent workhorse, the O’s let him walk as a free agent.

One and done.

Burnes went to Arizona for six years and $210 million, a price tag we should have realistically known Baltimore was never going to match.

The O’s gave up quite a lot to acquire Burnes last offseason.

Without him, there’s a significant hole in the top of the rotation — a hole 41-year-old Charlie Morton cannot fill, with all due respect.

That has led fans to peruse the trade market once again, with San Diego Padres ace Dylan Cease emerging as a popular hypothetical candidate.

The Padres won’t pay Cease at the end of the season and the recent signing of Nick Pivetta at least opens the door for A.J. Preller and the San Diego front office to consider a timely divorce.

Cease won’t come cheap, though. One has to think the Padres will ask about top MLB prospect Jackson Holliday. That’s where Baltimore needs to draw a line in the sand.

For more news and rumors, check out MLB Insider Robert Murray’s work onThe Baseball Insiders podcast, subscribe to The Moonshot, our weekly MLB newsletter, and join the discord to get the inside scoop during the MLB offseason.

Orioles simply can’t trade Jackson Holliday for Dylan Cease

Holliday struggled relative to expectations as a rookie, slashing .189/.255/.311 with five home runs across 190 ABs. He did finish strong, however, posting a more respectable .880 OPS over his final 10 games of the campaign. It’s always tough-sledding for rookies.

Holliday attempted the leap earlier than most, turning 21 just a few months ago. It should not come as a shock that MLB was a significant adjustment and required a patient hand.

The son of a former MLB All-Star, Holliday has been on a skyward trajectory since birth.

A tremendous profile on the talented middle infielder from MLB.com’s Peyton Stoike charts Holliday’s path from a kid hanging around the clubhouse to a future superstar.

“He just had a really fundamentally sound swing at two years old,” said Matt Holliday, Jackson’s dad. “People would stop and watch his swing, players on the team would stop and be like, ‘That’s not normal.’ He had a good swing and he could barely walk. He was always playing ball, and he was swinging at everything. He would pretend like everything was a bat. He was obsessed with all things baseball from a very young age.”

Stoike does an excellent job of outlining the unique circumstances of Holliday’s childhood as the son of an MLB star.

Not only did he get to watch first-hand as his father experienced the highest levels of professional success, but Holliday was taught about work ethic and staying engaged in the community.

Matt Holliday made a point to get deeply involved with each city he played in. That has clearly rubbed off of Jackson, who embraced Baltimore from the jump.

Like it or not, Holliday still has one of the highest ceilings in MLB. You just cannot trade him this early, especially not for a rental in Dylan Cease.

If the O’s weren’t going to pay Corbin Burnes, it’s hard to imagine a different outcome with Cease, who is arguably trending in a better direction these days.

Baltimore would take a substantial step forward with Cease in 2025, but nothing is guaranteed once the playoffs roll around. If the O’s were to fall short, lose Cease in free agency, and watch Holliday blossom into a perennial All-Star with San Diego — well, that just wouldn’t be very fun.

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