Orioles Jackson Holliday stubbornness could cost them Tarik Skubal and more

The Baltimore Orioles are off to a rollicking start at the trade deadline, adding Tampa Bay Rays pitcher Zach Eflin to supplement an injury-stricken rotation. Pitching is the primary area of need for Baltimore, and there’s still plenty of room to upgrade the roster. The O’s have no shortage of quality prospects at their disposal, to the point where Baltimore can outbid any MLB team if their will is strong enough.

Perhaps the most exciting name tied to Baltimore (or any team, for that matter) is Tarik Skubal. The Detroit Tigers fireballer is currently billed as the AL Cy Young frontrunner. He has unhittable high-90s heat and, at 27, Skubal has multiple years of team control left. The intersection of age, contract, and production is uncommon for a trade candidate, and it’s the exact sort of opportunity the O’s are built to take advantage of.
That said, Skubal won’t come cheap. According to Jim Bowden of The Athletic, Detroit doesn’t plan to trade its ace unless a team “significantly improves its offer to them.” The O’s, meanwhile, are hesitant to deal top prospects, and would prefer to deal either Ryan Mountcastle or Cedric Mullens in a trade for pitching upgrades. That strategy would all but ensure that Skubal, or even Chicago White Sox flamethrower Garrett Crochet, are off the table.

Orioles’ Jackson Holliday stinginess could lead to trade deadline disappointment
Baltimore has the best farm system in baseball, headlined of course by the MLB’s No. 1 overall prospect, Jackson Holliday. It has been a rocky season for the 20-year-old, who spent 10 games with the major league squad early in the campaign before his struggles forced a demotion to Triple-A. Holliday has not been raking at his accustomed level with the Norfolk Tides, but it would be foolish to write off such a gifted player before he reaches legal drinking age. Holliday has plenty to offer the O’s long term — or any team that acquires him via trade.

Floating Holliday in deals is a surefire way to get the Tigers’ ears to perk up a bit. Detroit desperately needs star power in its lineup. The bats in Motown simply aren’t up to snuff, and Holliday should be cranking out homers in the MLB before too long. Baltimore undoubtedly has the trade ammo to acquire Skubal, or really anybody. It’s all about want.

There are valid constrasting sides to this argument. On one hand, the Orioles are in poll position to win the American League and contend for a World Series. Why waste this opportunity by not going all-in, especially with so much uncertainty about Corbin Burnes’ future beyond this season?

On other hand, Baltimore has built — on paper — an exceptionally sustainable contender. This is a young team, with a young core, as well as the MLB’s top feeder system. As players age and become expensive, elite prospects will step in to patch holes and reinforce areas of weakness. The O’s could very well stick around the top of the American League for another decade-plus, with Holliday on track to become yet another Orioles All-Star somewhere down the line. Baltimore can boost its current odds by trading for Skubal, but that could diminish their ability to sustain this success long-term.

It’s worth noting that Skubal is awfully young at 27, and he would provide value for a long time if the Orioles are able to hammer out a second contract. The Scott Boras factor complicates those plans — Skubal will avidly test the free agent waters when the time comes — but Baltimore’s new ownership has displayed a true willingness to invest financially in the success of the team. The Burnes and Eflin trades are telling. If Baltimore puts forth the best offer, surely Skubal would re-sign.

That is easier said than done, of course, which is a major factor here. The Dodgers, Mets, Yankees, Phillies — these franchises are far more comfortable spending $300 million-plus on a star than the O’s, no matter who owns the team. If Skubal is a 2.5-year rental, that is less appealing than a 12-year rotation anchor. And, unfortunately, there’s no real way to tell the future, so parting with Holliday for Skubal would be a leap of faith.

We will see if the Orioles’ approach shifts in the next couple days, but right now, it seems thoroughly unlikely that Jackson Holliday will be moved at the deadline.