Reddit AMA: O's reporter Jake Rill chats about Henderson, Holliday, free-agent arms and more

8:30 PM UTC

On Wednesday, Orioles beat reporter Jake Rill held an Ask Me Anything on Reddit with fans at r/orioles. This mailbag features questions and answers from there. The full AMA can be read here. Questions and responses have been lightly edited for clarity.

What is the possibility of keeping and ? What are the tea leaves saying about their future? -- u/Lanky-Spring6616

Let’s go back to what agent Scott Boras said at Pete Alonso’s introductory press conference earlier this month, because I thought this was an interesting quote:

“Having calls from Jackson and Gunnar and [Jordan Westburg] after this was done, the light that it shines on how the players in that locker room feel about the commitment to how they can compete in really one of the toughest divisions in baseball, that comes organically,” Boras said. “The minute it’s done, it has that immediate impact, the excitement. I wish you all could hear it, because it’s meaningful. It gives them a sense of pride and confidence that illustrates that this franchise is committed.”

The Orioles now have a starting infield composed entirely of Boras clients -- Alonso, Holliday, Henderson and Westburg. Does Alonso signing a long-term deal with Baltimore mean the other three will follow suit? Not necessarily. But it doesn’t feel like it hurt for the O’s to have a successful negotiation with Boras via their signing of Alonso.

I think the odds of the Orioles signing guys like Henderson and Holliday to extensions are better than they’ve previously been, especially because this David Rubenstein-led ownership group has put its money where its mouth had been in terms of expressing a willingness to spend big.

Are the Orioles more likely to get a top-of-rotation guy via trade or signing? Also, what is the current view of the Orioles’ front office on the top free-agent arms right now? Are there concerns with some of them? -- u/Efficient_Wishbone93

It could happen either way, truthfully. The O’s are clearly willing to spend money, and it would make sense for them to splurge on one of the top free-agent arms. But if they can find a frontline starter on the trade market and assemble a package centered around somebody like Coby Mayo and some mid-tier prospects, that could get the job done, too.

It doesn’t feel like there are concerns about the top free-agent arms. It’s more so just the market being a bit slow to develop. Things should speed up once Tatsuya Imai’s negotiation window with MLB teams ends Friday at 5 p.m. ET. He’s a big domino that will fall and then allow teams to pivot to other options more aggressively.

What is your favorite food at Camden Yards? What excites you about this team the most, and who do you think will hit the first ball to Eutaw Street this year? Last question, how is the ballpark coming along and do you think its upgrades are good, positive and necessary? -- u/owls_ryani

1. Can’t not pick Boog’s BBQ, right? I’ve been eating those sandwiches at Camden Yards since I was a kid, so there’s nostalgia associated with those. But I also thought the corned-beef sandwich at the Attman’s stand this past season was quite good.

2. It’ll be fun to watch Alonso play every day, especially having not seen a ton of him in-person in recent years with him being in the National League. Not my pick for the first Eutaw Street home run, though (even if he hopes to eventually become the first right-handed hitter to make it there).

I just realized the other day that no Orioles homers hit Eutaw Street in 2025. All three to land there were hit by visitors. Weird, right? I’ll go with the easy pick of Henderson to end the drought early in ‘26.

3. A lot of framework has been put in place for the new videoboard, the new suite and the new press box last I saw. Not sure how much different it will look by the time I leave for Sarasota in early February, as they'll still have a month-plus to get everything done at that point.

The upgrades should be great. A few components of the ballpark had started to feel dated in recent years (the videoboards, the sound system, etc.), and this should help keep Camden Yards in the top tier of MLB ballparks. I’m looking forward to Opening Day to see how much better all of this will make the experience.