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.

During the first day of the Orioles offseason, executive vice president and general manager Mike Elias and manager Brandon Hyde took numerous questions from reporters trying to assess what went wrong again for the Orioles with a quick out in the playoffs.

Elias spoke for over 30 minutes.

After a 91-71 regular season, and 192 wins, the second-most in the majors since the start of last year, the O’s went 0-2 this October after going 0-3 last year against Texas.

“The expectations, I think, for this season were different. We didn’t meet them,” said Elias. “We all feel that. And it has applied a different kind of pressure that is new for a lot of people in this building. The big leagues can do that to you.

“I am optimistic, bullish, I believe in this group going forward, but it’s not going to just happen automatically. We’re going to have to put in the right work this winter. Everyone is going to have to look internally. Self assess, self correct.”

Ryan O’Hearn is treating today like it’s the first game of the Wild Card round. He’s being literal. He denies any motivation to get back at the Royals, who drafted him in 2014 and kept him in the majors for five seasons before the cash considerations trade with the Orioles in January 2023.

That’s his story, and he’s playfully sticking to it.

“Obviously you want to win every playoff game and every game you play,” he said this morning at his media session. “There's really no, like, revenge in my mind.”

Then came the slight pause and the kicker.

“You know,” he added, “even if there was, I wouldn't tell you guys.”

MINNEAPOLIS – The Orioles recalled reliever Colin Selby this morning and designated left-hander Tucker Davidson for assignment after he tossed 4 2/3 scoreless innings last night.

Selby is another fresh arm for the bullpen, with manager Brandon Hyde prepping his other relievers for availability in Game 1 of Tuesday’s Wild Card game.

Selby appeared in two games with the Orioles in August and didn’t allow a run or hit in three innings. He struck out four batters.

The Orioles haven’t committed to their Game 2 starter.

Albert Suárez gets today’s start, with uncertainty over how long he’ll pitch. Hyde was non-committal yesterday about possibly shortening Suárez.

MINNEAPOLIS – Another Wild Card roster meeting will be held when the Orioles return home. They must decide whether to carry 12 pitchers again, as they did in last year’s Division Series.

“I think everything’s on the table right now,” said manager Brandon Hyde.

The Orioles will host the Tigers or Royals. The seedings will be set later today. And they finally can begin clearing the table.

By optioning reliever Bryan Baker yesterday to the spring complex, the Orioles won’t have him available unless they reach the Championship Series. That’s one of the differences from last fall’s ALDS roster.

Baker was added to it after finishing his season with Triple-A Norfolk. Among the omitted were Cole Irvin, Shintaro Fujinami and Mike Baumann. Baker made one appearance against the Rangers, walked the bases loaded in the third inning of Game 2 and was charged with three runs when Mitch Garver homered off Jacob Webb.

MINNEAPOLIS – Matt Bowman jogged from the bullpen to the mound to begin warming tonight, keeping him in a familiar routine except for the inning. He isn’t accustomed to pitching in the first. He doesn’t normally face a leadoff hitter.

The Orioles used an opener. Tucker Davidson arrived for bulk relief work. They batted Jackson Holliday atop the order and started him at shortstop. A handful of regulars rested on the bench, only the third time for Gunnar Henderson. The perks of clinching a playoff seeding were flaunted.

Bowman struck out two batters in 1 1/3 scoreless innings and Davidson shut out the Twins over 4 2/3. Ryan O’Hearn and Emmanuel Rivera belted two-run homers off rookie Zebby Matthews and Rivera launched a solo shot off reliever Louie Varland. The Orioles secured the home Wild Card but they didn’t fold, powering past the sagging Twins 9-2 before an announced crowd of 30,558 brave souls at Target Field.

Bowman allowed one hit and threw 19 pitches in his first major league start, and first at any level since 2015 with Triple-A Las Vegas. Davidson, whose contract was selected earlier today, followed him and surrendered four ground ball hits.

"That was nice," manager Brandon Hyde said of Davidson. "He’s pitched in some big games in his career, and had a nice year in Triple-A. Awesome to see him get an opportunity and take full advantage of it tonight.”

MINNEAPOLIS – Jackson Holliday is making his first major league start at shortstop tonight against the Twins.

This is the “already clinched” lineup.

Gunnar Henderson, Colton Cowser, Cedric Mullins and Jordan Westburg are sitting.

Ramón Urías is playing second base. Emmanuel Rivera is at third. Austin Slater is the center fielder.

Adley Rutschman is catching Matt Bowman, who’s the opener.

NEW YORK – A win tonight and the Orioles would clinch the home Wild Card. A loss and the Yankees would finally pop champagne corks as division champions, the jubilation put on ice for the first two games of the series. The out-of-town scoreboard didn’t require watching. The important stuff was happening on the field.

The starting pitchers were worthy of the importance attached – former Cy Young winners Corbin Burnes and Gerrit Cole. Lay down your aces.

The Orioles are eyeing bigger stakes. They shuffled the deck, shortening Burnes to five innings and 69 pitches to freshen him for Tuesday’s assignment. And the game collapsed like a house of cards.

Burnes’ only mistake was a solo homer by Giancarlo Stanton. The Yankees scored six times in the sixth inning against three relievers, Aaron Judge delivered a towering two-run shot in the seventh, and the Orioles were eliminated from the American League East race with a 10-1 loss in the Bronx. They’ll try to secure the first Wild Card this weekend in Minnesota.

Cole shut out the Orioles (88-71) on two hits in 6 2/3 innings and the Yankees avoided the sweep.

Jordan Westburg’s return from the injured list yesterday pushed Jackson Holliday to the bench. Westburg wasn’t playing third base due to Ramón Urías’ simultaneous return. The setup was cemented.

The times are changing, and back to the norm.

Holliday won’t be buried but his opportunities to start could be impacted, and especially against left-handed opposing pitchers. Urías was the club’s hottest hitter at the time that his right ankle rolled on Aug. 31 in Colorado while he covered the bag on a stolen base. Sending him back to his previous utility role might have to wait until 2025 if he’s back with the club as expected.

Asked yesterday whether he’d stay with Westburg at second and Urías at third, with maybe the occasional starts for Holliday, manager Brandon Hyde said it depends how the Orioles are hitting.

“Ramón was swinging the bat great until he got hurt, swung the bat great today, and Westy will be in there,” he said. “So it’ll be day-to-day.”

The Kansas City Royals lost again, so the Orioles' four-game lead for the first American League wild card berth is still intact. But they had a chance to build some real momentum and get their mojo back.

It sure looked like they were doing exactly that, until they were not.

Most Valuable Oriole Gunnar Henderson doubled in two runs in the last of the ninth and the Orioles and Tigers were tied at four. More than 39,000 fans were roaring. Another walk-off seemed moments away.

Second and third, no outs. But no more runs. A 6-4 loss to Detroit in 10 innings was a gut punch.

A few random thoughts:

With one swing, the Orioles ended a losing streak and maybe relieved some pressure on their clubhouse. They have scored five or more runs just twice in the last 13 games.

The second time was Thursday afternoon when Anthony Santander hit a two-run walk-off homer in the ninth to beat the Giants 5-3.

Did that swing relieve some pressure on the clubhouse?

“Yean, I mean, whether you are winning or losing, there is always pressure. It’s the big leagues,” said catcher James McCann. “We are coming down to the wire here. It’s a matter of being able to handle that pressure. You know, things haven’t been going our way right now, so to finally break through after what seems like an extremely long stretch, this is big. Big for the guys and hopefully this is something we can build on.”

Santander hit No. 42 and produced his third career walk-off homer and the O’s first walk-off win since July 14, the final day of the first half.

Craig Kimbrel sat in front of his locker after the best and especially the worst of his outings. The clubhouse doors opened to the media and he’d be waiting for it. That’s a professional. He didn’t duck reporters and avoid uncomfortable questions about his demise as closer in the second half, how he tried to fix it and why he failed.

The stats will be regurgitated and rightfully so. This is a results-driven business and Kimbrel didn’t produce or provide a sufficient return on the largest contract awarded under executive vice president/general manager Mike Elias.

Kimbrel wasn’t supposed to be Félix Bautista, but he also wasn’t supposed to be Jorge Julio.

It’s worth a reminder, however, that there’s a person behind the inflated ERA, WHIP and blown saves. The Hall of Fame candidate who provided leadership for a bullpen still short on experience. He set an example, and that included how to handle adversity and not redirect it to innocent parties. Place it where it belonged, on his shoulders.

The last time we saw Kimbrel was after manager Brandon Hyde’s media session that followed Tuesday’s 10-0 loss and the career-high six runs that had many fans booing him. Kimbrel sat on a bench outside the clubhouse with wife Ashely and young children Lydia and Joseph, in full dad mode, as if everything was right in his world.