Tarik Skubal for Jackson Holliday? Orioles Face Critical Trade Deadline Crossroads

The 2023 postseason marked a successful rebuild for the Baltimore Orioles, ending a six-year playoff drought that wrought a 336-534 record, four last-place divisional finishes and a bevy of top draft picks.

Now, though, the Orioles have one of the best records in baseball plus a top-tier farm system led by 2022 first overall pick Jackson Holliday. With their rebuild complete, the Orioles are faced with the next step toward championship contention, looking to bolster their roster ahead of the trade deadline. And the biggest question facing general manager Mike Elias is just how much of the future is worth leveraging for the present.

The Orioles must pursue a trade for Tarik Skubal

There’s no question the Orioles need to bolster the pitching staff if they want to take the next step toward championship contention. They were swept in the first round last year as their pitchers posted a painful 7.27 ERA against the Texas Rangers. Elias and company addressed that shortcoming in a big way over the offseason by acquiring Cy Young Award winner Corbin Burnes, but with three of their starters currently on the injured list, it seems like more reinforcements are needed.

Elias is surely prepared to dip into his prospect depth to address that need this month, but how much future potential is he willing to leverage for a win-now boost?

“While the Orioles’ No.1-ranked farm system and their major league roster are loaded with young position players on cheap contracts — making it possible for them to swing a trade for virtually anyone in the league — consolidating several controllable players for one at the most injury-prone position in sports is a significant gamble,” The Baltimore Sun noted.

If there is any player on the trading block who can tempt Elias to take that gamble, it would be Detroit Tigers starter Tarik Skubal. The 27-year-old ace is currently the odds-on favorite to win the American League Cy Young Award, with a league-leading 2.34 ERA and 146 strikeouts in 20 starts.

With two more years of arbitration eligibility ahead for Skubal, the Tigers face no real urgency to deal him, even as they face the prospect of a light rebuild sitting outside of the playoffs with a losing record. But with Skubal having a career season, getting a major prospect haul in return might be enough to motivate the Tigers to feel they are selling high.

“Sure, it might cost a lot to swing a trade for a Skubal,” the Sun added. “It might also leave them one key piece short in their quest to bring a World Series title to Baltimore for the first time since 1983 if they don’t.”

The Orioles are being warned not to trade away Jackson Holliday

Even if the time has come for the Orioles to aggressively pursue a World Series, insiders are warning Elias not to give up Holliday in the process.

“Skubal has two-and-a-half years of control versus six years of Jackson Holliday, who might be an All-Star position player,” Fox Sports reporter Ken Rosenthal said . “There’s no question he’d be an upgrade to the rotation in Baltimore, but, I’m sorry, I ride Jackson Holliday as my starting second baseman going forward.”

Elias might see Holliday as untouchable, but the rebuild in Baltimore has gone so well that he can assemble a compelling trade package for Skubal even without him.

“I think if the Orioles offered a package that included Heston Kjerstad or Colton Cowser, (Coby) Mayo and Cade Povich, it would be hard for the Tigers to turn down based on where they are in their rebuilding process,” noted The Jim Bowden of The Athletic. “It would be a steep price to pay for Baltimore, but worth it to be able to have a postseason rotation of Corbin Burnes, Skubal and Grayson Rodriguez.”

The Orioles are under pressure to improve their pitching staff with just a few days until it will be too late. It seems they can land a game-changer like Skubal without losing Holliday and that might be the route Elias goes.

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