Orioles latest offseason whiff makes Jackson Holliday trade more likely than ever

The Baltimore Orioles need a new ace, as Corbin Burnes – who they acquired last winter courtesy of the Milwaukee Brewers – is the top starting pitcher available on the market. Blake Snell received a five-year, $182 million contract. Burnes is likely to receive a higher AAV and, given he is a year younger, a longer deal.

Baltimore can go two routes here. They can opt to sign pitchers in free agency and replace Burnes by committee, or they can trade for a player like Garrett Crochet. The latter option is their best bet as Mike Elias and the O's have one of the best farm systems in MLB. Assuming Baltimore is done prospect-hoarding (and they ought to be after losing to the Kansas City Royals in the AL Wild Card round), acquiring Crochet for prospects is their best course of action moving forward.

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Would the Orioles consider trading Jackson Holliday this winter?

Now, I'd imagine the Orioles would drive a hard bargain as it pertains to trading Jackson Holliday, who is still only 20 years old. Holliday struggled at times last season, and slashed just .189/.255/.311 in 190 at-bats, good for a WAR of 0.1, but he lit up the minor leagues and projects to be a perennial AL All-Star candidate. Holliday also has genes on his side – yes, really – as the son of former Rockies and Cardinals great Matt Holliday.

The issue for the Orioles is a simple one. They cannot afford the likes of Burnes or Max Fried in free agency, and the pitching market is relatively top-heavy as compared to years past. Crochet still has a few years left on his deal, and he's cheap in terms of price tag. The Orioles would want to extend Crochet eventually, but the front office could take their time knowing Crochet is an ace-level pitcher they can build around. He's also only 25, which explains why he's so expensive.

Adding Holliday to the Crochet trade package would make the southpaw far easier to acquire. The White Sox want high-level position player prospects. Holliday is just that.

The Orioles don't want to deal away the entire farm, as they value their organizational depth. Trading Holliday means less prospects sent to the south side of Chicago overall, as tough as parting ways with Jackson would be.

A Jackson Holliday trade is never likely, but it's more realistic today than it's ever been before.