4 extensions the Orioles must prioritize when new ownership takes over

Jackson Holliday

Speaking of players that haven't made their big league debuts yet, Jackson Holliday sticks out as the lone true prospect the Orioles should consider extending. Holliday is another case of a No. 1 overall pick living up to the hype. After being the top pick out of high school, he posted a .911 OPS in his pro debut, and then was even better last year in slashing .323/.442/.499 with 12 homers and 24 stolen bases.

At the moment, the biggest question is whether or not Holliday will make the Orioles' roster right out of camp. Given the way he has played this spring, the odds continue to look good that he will be in Baltimore on Opening Day. If the Orioles really want to get the best possible price on an extension for him, they really need to try to do so sooner rather than later.

Again, we encounter a familiar problem in Scott Boras, as he is also Holliday's agent. Boras' ties to the Holliday go back to Jackson's dad, Matt, and his playing days, and Boras definitely got his dad paid when the time came. It is also important to remember that to bring Holliday into the fold in the first place, Baltimore had to fork over the largest signing bonus ever given to a high school draft pick.

The odds are definitely stacked against the Orioles when it comes to a really early contract extension for Holliday, but they still need to try. As is the case with Henderson, Baltimore has been staying in touch with Boras about Holliday, and who knows? Maybe the two sides can work something out over the next couple of years. The closer Holliday gets to free agency, however, the less likely that any sort of extension could get done at all.

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