Today, it’s another edition, our pre-Holiday edition, of several questions for O’s fans. Per usual, answer one question or all of them. Respond to other readers' answers with your takes on their takes. 

On to the questions:

1) Where does right-hander Tomoyuki Sugano slot into the O’s rotation? And after going 15-3 with a 1.67 ERA in Japan, how well will he do for the 2025 Orioles?

2) Which player will bat leadoff the most next season?

3) Which player will lead the 2025 O’s in home runs and hit how many?

For the Orioles in recent years, seeing a highly-ranked prospect come up and produce right away has been a challenge. Frankly, it’s a challenge for a lot of players and teams.

Any move up the minor league ladder can be a challenge for a young player but the move to the majors is the hardest. Hard to get there, sometimes harder to stay there.

The O’s can go back to Cal Ripken Jr. to see his rough start in the majors. More recently, then No. 1 ranked prospect Adley Rutschman came up in May of 2022. After his first 20 big league games, he was batting .176 with no homers or RBIs. Colton Cowser hit .115 in 2023, and Grayson Rodriguez had an ERA of 7.35 his first 10 MLB starts. Now he’s a top of the rotation type pitcher.

In 2024, elite prospects like Jackson Holliday and Coby Mayo had some big-time MLB struggles.

During the Winter Meetings, O’s director of player development Anthony Villa was asked about how the organization can try to help their top prospects get off to better starts when they arrive in the big leagues?

The Orioles, as they did during the 2024 season, will have three hitting coaches working with their position players again in the 2025 year.

This time around, Cody Asche returns to the staff as primary hitting coach. The assistant hitting coaches are Sherman Johnson and Tommy Joseph. Johnson will also serve as upper level hitting coordinator.

Johnson, 34, spent last season as the O’s minor league upper-level hitting coordinator. He was the hitting coach at Triple-A Norfolk in 2023, his first professional coaching position after a nine-year playing career.

Joseph, 33, completed his first season as an MLB coach in 2024 as the assistant hitting coach for the Seattle Mariners. He joined the Mariners after three seasons as a minor league hitting coach for the San Francisco Giants with High-A Eugene in 2023 and with the New York Mets for Double-A Binghamton in 2022 and Single-A St. Lucie in 2021. Joseph appeared in 249 MLB games with the Phillies from 2016-17.

Asche, 34, spent the last two years as the O's offensive strategy coach. He served as the organization’s upper-level hitting coordinator in 2022. He was also a guest on a recent addition of the “Hot Stove” radio show on WBAL Radio.

The Orioles are not guaranteeing that Jackson Holliday will be their starting second baseman when the 2025 season starts, but it’s pretty clear they expect exactly that result.

At age 20 in 60 games last season, he hit .189/.255/.311/.565 for an OPS+ of just 66.

His struggles led some fans to question how he became the No. 1 ranked player in the minors and to question his potential? I can remind you how – he earned it.

I asked manager Brandon Hyde this week if Holliday is his guy at second base?

“Think we’re going to give him every opportunity,” the skipper said. “Loved the way he finished the season last year (going 4-for-5 the last weekend). I like the swing adjustments that he’s made. I just talked to him yesterday, he feels great. And you know, he’s a big part of the future for us. We’re going to give him every opportunity this spring.”

The Orioles conducted their business yesterday in the Rule 5 draft, watching seven minor leaguers leave the organization, and headed back home still short at least one starter and reliever. The meetings with agents and executives were plentiful. Perhaps they were able to make significant progress toward a deal. But the only announcements were the signings of outfielder Tyler O’Neill and catcher Gary Sánchez three days after their agreements.

Trading for an ace like the Padres’ Dylan Cease or Seattle's Luis Castillo - the Mariners want a right-handed hitting first baseman - is becoming the more likely avenue with free agents flying off the board. Garrett Crochet went to the Red Sox, so he’s out. Otherwise, executive vice president/general manager Mike Elias will need to lower his sights to the middle of the rotation on shorter-term deals or bust the bank for Corbin Burnes.

While the pitching staff is incomplete, the biggest questions surrounding the lineup and bench center on who makes the club and the amount of playing time.

Elias didn’t offer any guarantees Tuesday about Jackson Holliday getting most of the starts at second base, and he listed the factors that could influence it.

“It’s gonna depend on a lot of things - on the lineup, who’s healthy, who’s pitching, who’s in that Opening Day lineup. But I think we’re gonna see a big step forward from Jackson this year,” Elias said during his media session.

The shakeup of the major league coaching staff, particularly on the hitting side, isn’t leading to a massive change in philosophy, instruction and reliance on analytics and data.

It’s more about self-examination and perhaps some tweaking. Evolve rather than overhaul.

Cody Asche is the lead hitting coach after serving as offensive strategy coach for two seasons. Upper-level hitting coordinator Sherman Johnson also will serve as an assistant hitting coach, and the Orioles hired Tommy Joseph for the same role.

“I think we’ve always had an attraction to what is described as a modern coach,” said assistant general manager Sig Mejdal. “That’s someone who inspires the players, has their respect, but also doesn’t shy away from questioning convention, looking at data, looking at technology, and that describes Cody and Sherm very well.”

The Orioles have been swept in the playoffs in the last two seasons and managed only one run in 18 innings against the Royals in the Wild Card round. They went 1-for-13 with runners in scoring position, a continuation of their struggles over the second half.

The Orioles haven’t found their starting pitcher in Dallas and they aren’t done with the bullpen. The work continues today and through the offseason. The last day of the Winter Meetings isn’t a deadline to finish the roster.

Is there anything else to do with position players?

The club appears set barring a trade, though it’s Dec. 10 and a lot can happen. The 13 non-pitchers right now are easy to identify.

We know the catchers - Adley Rutschman and Gary Sánchez. We know that Colton Cowser, Cedric Mullins, Heston Kjerstad and Tyler O’Neill are expected to be the four outfielders. And we know that it leaves room for seven infielders, which on paper read as Gunnar Henderson, Jordan Westburg, Jackson Holliday, Ryan Mountcastle, Ryan O’Hearn, Ramón Urías and Jorge Mateo.

Top prospect Coby Mayo and Emmanuel Rivera, who signed a one-year contract for $1 million and is out of minor league options, appear to be on the outside. To get either one of them in the picture might require dealing an infielder.

Last year’s Winter Meetings appeared to confirm the handful of Orioles prospects deemed untouchable, at least to some rival executives - a group that included Jackson Holliday, Coby Mayo and Heston Kjerstad.

This week could present an opportunity for media in Dallas to glean whether some statuses have changed.

Holliday projects as the starting second baseman after a rough introduction to the majors, where he batted .189/.255/.311 with 69 strikeouts in 60 games. He’s made an adjustment at the plate, removing the leg lift as a timing mechanism and going with a toe tap, and the Orioles maintain a high opinion of a player drafted one/one and who ranked as the top prospect in baseball.

Jordan Westburg, Jorge Mateo and Ramón Urías also can play second, giving manager Brandon Hyde infield flexibility. But the ideal setup has Holliday at second, Westburg at third and Urías and Mateo working in utility roles. Mateo also could be an extra right-handed hitting outfielder.

Kjerstad could find many more opportunities bouncing between the outfield and designated hitter. The Orioles signed Tyler O’Neill to replace Anthony Santander, but Kjerstad offers the contrast of a left-handed bat.

For someone who covers the minor leagues as I do it is a question to ponder: When referring to the Baysox moving forward, do I go with Chesapeake, their new name, or in some cases is Bowie still acceptable?

A case like when I refer to a player who spent time in 2024 with the Baysox. They were still Bowie then, so do I say this player hit such and such at High-A Aberdeen and this number at Double-A Bowie? Or just use Chesapeake?

There is no handbook and there are no right or wrong answers.

But in noting some recent stories in this space, I did report on the name change to the Chesapeake Baysox.

“I think when we looked at where our fans are coming from, we wanted to be inclusive of the entire Chesapeake Bay watershed,” said Brian Shallcross, in his 20^th year as Baysox general manager. “We saw people coming from the Eastern Shore, west of the Potomac. We were surprised when we dug into the stats of just how far and ranging our fanbase was. We wanted to be inclusive of all those fans without forgetting our roots.”

The trend for O’s young players and some of the top prospects in the last year or two has been to come to the big leagues and struggle initially. It doesn’t happen every time, but it has happened a lot of the time.

Right-hander Grayson Rodriguez and outfielder Colton Cowser are two prime examples. In his first 10 MLB starts during the 2023 season, Rodriguez went 2-2 with a 7.35 ERA and .956 OPS against. It got better for him. During that same ’23 season, over 77 plate appearances (yes, a small sample) Cowser hit. 115 with an OPS of .433.

Rodriguez, as was Cowser, was sent back to the minors after those initial struggles in 2023. In July of that year he came back a different pitcher. In fact, in his last 33 games, he has gone 18-6 with a 3.35 ERA and 1.18 WHIP. He has 18 quality starts allowing a .237 batting average and .664 OPS. His groundball rate is 45.7 and that helped him keep the ball in the park allowing 0.84 homers per nine since that July 2023 date.

Cowser just posted a second-place finish for the AL Rookie of the Year, losing out to Yankees right-hander Luis Gil after a strong first full season in the majors.

Watching Rodriguez go from pitching to a 7.35 ERA to pitching like a No. 1 or No. 2 starter and watching Cowser go from hitting .115 to getting Rookie of the Year votes, reminds us it can take a while for young players to reach their potential or to trend up on the stat sheet.

The mailbag is stuffed again like a Thanksgiving turkey.

I’ll do my best to provide answers but at times will just have to wing it.

This is the latest sequel to the beloved 2008 original. Editing rules are trashed like a two-week-old green bean casserole.

Also, my mailbag carves the turkey at the head of the table and your mailbag heats up a Hungry Man dinner.

Which unprotected players are most vulnerable in the Rule 5 draft?
Before I begin, let’s remember that losing a player in the Rule 5 draft doesn’t mean he won’t come back to the organization. It’s hard to carry one throughout a season. OK, pitcher Alex Pham is the No. 25 prospect in the system per MLB Pipeline and he had 138 strikeouts in 119 innings at Double-A Bowie. Reliever Keagan Gillies had a 4.94 ERA with the Baysox, but he fanned 54 in 47 1/3 innings and surrendered only four home runs. He’s averaging 11.4 strikeouts per nine innings in the minors. He’s an interesting guy, but again, challenging to stash in a major league ‘pen.

Even in going 0-5 in the last two postseasons, one thing that must be of some comfort for Orioles fans moving forward is that their team should be good again. Both in 2025 and likely for years beyond that.

The Orioles' window to win, as they call it, seems wide open and vast.

The current group plus players that get added should make another run next season and maybe for several years after that.

But having a large window does not mean you will win a championship. It would seem likely to increase the odds, said Captain Obvious. But the Captain also noted that when the Dodgers won this year it was just their second title since 1988, and one came in a shortened season. That is a span of 36 years. In losing the World Series, the Yankees are now without a championship since 2009. That is 0-for-the-last-15 years even though they made 11 playoff appearances in that time.

It's hard to win it all, no matter how good your team is.

I want to thank reader and commenter Peter Wood for posing this question back in September that I thought was an interesting topic to address in the offseason: Who do we think will have a better career, Dylan Crews or Jackson Holliday?

It is, of course, way too early to make any proclamation one way or the other. But with each playing a substantial amount in the major leagues this season, there are significant data points to start the conversation.

Crews and Holliday are both highly touted young players and former No. 1 overall prospects in the sport. The Nationals got Crews out of Louisiana State with the No. 2 overall pick in 2023. Holliday, out of Stillwater High School in Oklahoma, was the No. 1 overall selection when the Orioles drafted him in 2022.

Both youngsters were anticipated to make their big league debuts this year, which they did. In fact, they each had a shot at making his respective team’s Opening Day roster. Many around the league believed that leaving Holliday off the Orioles roster to start the season was a surprising snub.

And so it was that both prospects started the year in the minor leagues, with Crews at Double-A Harrisburg and Holliday at Triple-A Norfolk.

Let’s dive into the first post-World Series mailbag while the offseason heats up.

You ask again, I answer again, and we have the latest sequel to the beloved 2008 original.

This is a politics-free mailbag. Let’s consider it practice for next week.

It’s also an editing-free mailbag. Let your clarity, length and style shine.

An important reminder here that my mailbag gets lots of candy on Halloween and your mailbag gets a toothbrush and dental floss.

The Orioles haven’t swung at a pitch or thrown one since Oct. 2 in Game 2 of the Wild Card series against the Royals. Gunnar Henderson struck out on a changeup from Lucas Erceg and walked back to the dugout with his head down. The visiting team celebrated in its clubhouse and on the field.

"Feel terrible," said Ryan O'Hearn. "Feel terrible for our fans. Feel like we let them down. Just sucks.”

What can the Orioles do next season to say that they’ve lost that losing feeling?

Here are three more ways:

Adley Rutschman being the best version of himself.

The mailbag is filling up again, like the bases in the bottom of the 10^th inning in Game 1 of the World Series.

Freddie Freeman isn’t here to empty it, so I’ll take over.

You ask, I answer, and we have our latest sequel to the beloved 2008 blockbuster. I thought about editing for clarity, length and style, until I had a moment of clarity and decided against it.

Also, my mailbag clinches pennants and yours clutches pearls.

Can you get more specifics on Colton Cowser's hand surgery? Having broken my hand playing ball back in the day where I just got casted and healed for weeks, I am curious as to what they corrected with his surgery.
Sorry, but the Orioles aren’t sharing any information beyond how he had “successful surgery to repair a fractured left hand, and the procedure “was performed by Dr. Donald Sheridan in Phoenix, AZ,” and that the outfielder “is expected to be ready for spring training.” Anything else must come from Cowser during his next media availability.

The Orioles play their first spring training game on Feb. 22 against the Pirates in Sarasota. We're waiting for the report dates.

Here are a few more topics that should garner a lot of interest.

Kyle Bradish and Tyler Wells.

We have a tendency to lump together players for certain reasons, like anytime that the Orioles bring two Rule 5 picks to camp.

Injuries create a similar dynamic.

The offseason halts play for the Orioles but can't stop the mailbag.

This is the latest sequel to the beloved 2008 original. Same rules apply. You ask and I try to answer. I don't believe in editing, but I believe in love.

Also, my mailbag sweeps other mailbags and yours sweeps the confetti that fell after my latest championship.

Any updates on Tyler Wells for 2025?
None. He was back with the team for the postseason but probably won’t pitch next summer until the second half. The question is how deeply into it. His return from June elbow surgery is supposed to be quicker because he underwent a revision ulnar collateral ligament procedure with UCL repair and internal brace augmentation. It requires less recovery time than the traditional Tommy John surgery. Maybe he gets back before Kyle Bradish, but a first-half return seems really optimistic.

What is the logic/benefit to having multiple hitting and/or pitching coaches? During the season whenever a pitching coach headed for the mound, it was only one of the two. It's not like they sent both out together.
That’s a funny image. The jobs are considered so big now that they require two coaches. Like having co-hitting coach Matt Borgschulte working with a player in the cage during a game. Having two pitching coaches to offer instruction to the large groups at spring training. Two who can wade through all of the analytic data and video. A second coach also can focus on advanced preparation for the next opponent. Two voices with one message. The Orioles aren't bringing back co-hitting coach Ryan Fuller. Here's what manager Brandon Hyde said about the co-hitting coach approach during his season-ending press conference: "Yeah, hitting coach is a tough job, because you're never going to have 13 or whatever guys going at the same time. You're going to have three guys going, you're going to have three guys struggling, and you're going to have six guys kind of in between, and it changes every three or four days. So it's a really, really tough job. Hitting is so hard to do. I think our guys do an amazing job of preparing our guys. I think they're unbelievably likable. Guys love to hit with them in the cage. They're incredibly prepared, they're unbelievably positive, and they're living and dying with every single one of our guys’ at-bats. That's all you can ask for."

The uncertainties over the Orioles’ roster for 2025 include how they intend to use Heston Kjerstad. Will he receive an opportunity to play every day, no matter the matchup, and how many starts will he get in the outfield?

Some stability would be a nice advancement for the second-overall draft pick in 2020.

Kjerstad was optioned multiple times and had multiple stints on the concussion injured list. He totaled 39 games and 114 plate appearances, batting .253/.351/.394, and made his second playoff roster.

It’s hard to label Kjerstad’s usage as a platoon because he didn’t play regularly, but he had only 16 at-bats against left-handers and collected six hits.

Manager Brandon Hyde was asked at his season-ending media session about platooning some of the younger hitters.

Players were in a daze or deep inside their emotions after Game 2 of the Wild Card. Media chased after veterans like Anthony Santander and Corbin Burnes, who could leave via free agency and made sense to speak about the jarring finish to the season. Young stars like Gunnar Henderson and Adley Rutschman stood at their lockers with tears in their eyes and tried to express how much they hurt. Jordan Westburg sat with his head lowered, aware that he’d also draw a crowd. Colton Cowser, a leading candidate for Rookie of the Year in the American League, first had to address his fractured left hand before delving into the loss. 

Jackson Holliday, the first-overall draft pick in 2022 and former No. 1 prospect in baseball before graduating from eligibility, quietly got dressed at his locker near the entrance. He didn’t play in the postseason and was in the lineup only once after Sept. 21, starting at shortstop a week later in Minnesota so that manager Brandon Hyde could give Henderson a rare break.

Holliday went 3-for-4 with a double and two walks and was 1-for-1 with a walk the next day in a reserve role. A nice finish after going 2-for-34 in 10 April games and packing his bags for Triple-A Norfolk, hitting a grand slam onto Eutaw Street after returning on July 31 but going 21-for-96 with 33 strikeouts in August and 12-for-55 with 17 strikeouts in September.

Reporters and other credential-wearing folks finally made it to Holliday, some just drawn by the convenience of having the kid reachable as opposed to the huge scrums that made it much harder to hear players. He wasn’t as qualified at age 20 to impart wisdom or to offer a deep dive into the offensive shutdown while spending both games on the bench. But he’s Jackson Holliday and that’s a good enough reason.

Holliday came with his own storyline. His first major league season, being optioned and finishing with a .189 average and .565 OPS in 60 games. His first time confronting failure. What he learned from it. And the joy of being on a playoff team.