As the MLB trade deadline approaches, Tigers fans are lost in a maze of maybes. After a decade-long drought of irrelevance, the Tigers, teetering around .500, have reignited excitement not felt since the 2014 playoffs. As the trade deadline looms, fans are like gardeners, unsure whether to prune their prized roses or let them grow wild, fearing both stagnation and over-cutting.

I don’t blame any fan for being confused or torn between scenarios.

What everyone needs to know is that this trade deadline is the most unique moment in Tigers baseball history.

The Tigers have Tarik Skubal.

The Orioles need Tarik Skubal.

The state of each organization could lead to the most historic trade in MLB history.

A Historic Trade Deadline

Many fans look to history for comparable trade packages the Tigers might receive. However, there is no trade to compare this to—not Juan Soto from the Nationals to the Padres, not Chris Sale from the White Sox to the Red Sox. Nothing.

The Value of Tarik Skubal

Tarik Skubal, the Tigers’ 27-year-old ace, is arguably the best pitcher in baseball this season. He is a savvy, hard-throwing lefty with a bulldog mentality on the mound. Currently, he leads the American League in ERA (2.34) and is the front-runner for the AL Cy Young Award. Skubal is under team control for this season and the next two seasons, making him an extremely valuable asset. These attributes would typically command a strong return in a normal market.

So, why would the Tigers consider trading someone like that?

It’s not a normal market. The unique circumstances of the Baltimore Orioles make this a historic moment.

The Orioles’ Unique Situation

The Orioles are uniquely positioned to offer a historic trade package, driven by a rare combination of having the best farm system in baseball and a legitimate shot at the World Series. Their top prospects are not just good; they are potential generational talents.

The Orioles are sitting in first place in the AL East, 1.5 games ahead of the Yankees and seven games ahead of the Red Sox. The Orioles’ biggest weakness is starting pitching. With two of their starters on the injured list, they desperately need a pitcher like Skubal.

Their current ace, Corbin Burnes, is an unrestricted free agent after the season and not expected to re-sign. Pairing Skubal with Burnes would make the Orioles immediate favorites this season and strong contenders for the next two years, even without Burnes.

This urgency is further amplified by the fact that the Red Sox and Yankees, their closest rivals, are also in dire need of starting pitching. The Orioles’ front office knows that securing Skubal not only strengthens their rotation but also keeps him away from their competitors. This potential bidding war could drive up the price for Skubal even higher.

Generational Prospects

The Orioles possess the best farm system in baseball by a wide margin. Within that system is Jackson Holliday, a generational shortstop prospect. Holliday, drafted first overall in 2022, is a can’t-miss player with superstar potential. The Tigers would likely require Holliday as the primary trade piece, along with either 3B/1B Coby Mayo or C/1B Samuel Basallo and two out of three players from OF Dylan Beavers, RHP Chayce McDermott, and LHP Cade Povich. Ideally, the Tigers would aim for a package including Holliday, Mayo, and Basallo, but that might be too rich for the Orioles.

Jackson Holliday is the top prospect in all of baseball, a rare talent expected to be a future star. Coby Mayo is a strong hitter and versatile infielder ranked as the 15th best prospect. Samuel Basallo, a catcher with exceptional skills, is ranked 12th. These prospects are not just top-ranked; they are nearly major league-ready, which is rare for players of their age and potential.

Why would the Orioles consider trading them?

This is what makes this trade scenario unlike any we’ve ever seen before.

Blocked by Stars

Gunnar Henderson, their current MLB shortstop, is an MVP frontrunner, effectively blocking Holliday’s path. Similarly, All-Star Jordan Westburg limits opportunities for Mayo, and Adley Rutschman, the top catcher in MLB, obstructs Basallo’s advancement. These prospects are stuck behind young stars and superstars on the Orioles’ roster, creating a unique situation where trading them may make sense.

Trading Skubal for a package of top prospects might sound crazy, but these prospects are not typical.

The Orioles, with their wealth of young talent, can afford to trade these players without significantly weakening their farm system.

Transforming the Tigers’ Infield

A trade package including Holliday, Mayo, and Basallo would provide the Tigers with major league-ready talent. This infusion of young talent could transform the Tigers’ infield overnight and set them up for long-term success. Currently, only Colt Keith is seen as close to a sure bet to hit in the big leagues, but his defensive struggles might move him to first base. The Tigers lack sure solutions at first base, shortstop, third base, and catcher.

A trade with the Orioles could transform their 2025 infield to Keith at first, Jace Jung at second, Holliday at shortstop, Mayo at third, and Basallo at catcher. If Basallo needs more minor league time, Jake Rogers and Dillon Dingler could fill in until he’s ready.

The Tigers’ Dilemma

“But Matt,” you might be thinking to ask, “the Tigers finally have a bona fide ace, a star pitcher, a player we love watching take the mound every five days, why in the world would we trade him?! Can’t we just build around him?”

That is a totally fair thought. Why would anyone want to be a fan of an organization that only trades their best players? I certainly wouldn’t like that. However, to turn down a trade like the one proposed hypothetically with the Orioles, the Tigers would need to make significant financial moves to build around Tarik Skubal before his contract is up at the end of the 2026 season.

Financial Considerations

Keeping Skubal and building around him requires significant financial moves. The Tigers need to sign several high-priced free agents, improve their bullpen, and buy out Javier Baez’s contract. The Tigers would also need to offer Skubal a record-breaking contract. Gerrit Cole’s nine-year, $324 million contract with the Yankees could serve as a benchmark, but Skubal’s deal might reach $400 million over eight years.

To make it worth it, consider these variable:

President of Baseball Operations Scott Harris must have the green light from ownership to pursue and sign proven MLB talent to support prospects and to sign Skubal long-term. Top Tigers prospects in Single and Double A are two years from contributing at the MLB level, with question marks at Triple A. Thus, the Tigers need to buy big-time free agents on multi-year deals, as trading prospects won’t command proven MLB talent.

The Tigers need to sign two to three bats, each commanding $15-$30 million annually. They also need one or two top-of-the-rotation pitchers (#2 or #3 type arms) and multiple swing-and-miss bullpen arms, a current organizational weakness. Additionally, the Tigers must buy out shortstop Javier Baez, who has three years and $73 million left on his six-year, $140 million contract signed in 2022.

Since MLB has no salary cap, these moves are possible. However, they contradict the track record of the Tigers’ ownership and Scott Harris’ typical front office maneuvers.

Scott Harris, a wunderkind in talent identification, seems to have hit on his first draft class with OF Max Clark and INF Kevin McGonigle. His strategic trades brought in INF Hao-Yu Lee, thriving in Double-A, and OF/DH Justyn-Henry Malloy, who is finding his stroke at the big league level after a mid-season call-up.

All these moves would cost Tigers ownership a significant amount this winter. But there’s more…

They also need to spend on Tarik Skubal.

If they pass up a historic trade to keep Skubal, they must sign him long-term. The cost is uncertain but would likely be a record-breaking contract for a pitcher (excluding the $700 million contract unicorn Shohei Ohtani signed with the Dodgers as a pitcher and hitter).

Skubal is represented by Scott Boras, an agent known for taking clients to free agency rather than signing extensions early. For Skubal, we can look at Gerrit Cole’s 2020 contract with the Yankees, also negotiated by Boras. Cole, at 30, signed a nine-year, $324 million contract. Considering inflation, Skubal and Boras might seek an eight-year, $400 million deal.

The Market Reality

$400 million is a lot of money for any player. It’s certainly a lot of money for a player who only plays for your team once every five days.

It’s a conundrum, but it’s also the reality of the market! Justin Verlander (41) and Max Scherzer (39) are currently the highest-paid pitchers at $43.3 million per year, followed by Jacob DeGrom (36) at $40 million per year, and Gerrit Cole at $36 million per year.

Could the Tigers offer him a six-year, $300 million contract to make him the highest-paid pitcher annually in MLB, avoid the next two arbitration years, and give him another free agency opportunity at 33-34? They could, but as mentioned, it’s unlikely Boras would agree.

This path to contention is possible but expensive, requiring an immediate and costly strategy this offseason.

Considering the uncertainty of the Bally Sports broadcasting mess affecting both of Ilitch’s teams and the possibility of building his own network, the expensive route seems like a stretch for the Tigers.

Still confused?

Voices are amplifying every rumor and theory, making it impossible to discern a clear path forward.

But I hope this cleared up some questions about the route the Tigers could take at the deadline.

As we inch closer to the trade deadline, remember this: Scott Harris and the Tigers hold all the power. They have difficult organizational strategy decisions to make, but they can easily reject any offer for Skubal that doesn’t have franchise-altering implications.

Most fans want to keep Skubal. Most fans want to win. The overwhelming majority want to keep Skubal and win.

What’s the smartest route to contention for the Tigers, and how long will it take?

We will learn so much about this team in the next seven days.

Buckle your seatbelts and hang on tight.

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For more from our Detroit Tigers beat writer, Matt Broder, check him out on Twitter here: @mattbro21

Contact: Broder@woodwardsports.com

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Original Photo Credit: © Junfu Han / USA TODAY NETWORK