What Went Wrong with The Baltimore Orioles

By: Danny Sheeler

12 Min Read

In June of 2019, the Baltimore Orioles took Adley Rutschman with the 1st overall pick of the MLB draft and Gunnar Henderson with their 2nd round pick. Two names that would become household names in the organization and around the city of Baltimore for years to come. While that year for the Baltimore Orioles was a complete shitshow, the selection of Rutschman sparked hope for a failing franchise for a city desperate to bring the true culture of baseball back into Baltimore. While the selection of Gunnar wasn't "groundbreaking" at the time, he would become one of the biggest names in MLB over the next 5 years and what fans thought to be their franchise shortstop. Fast forward 7 years later, Gunnar Hendeson simply isn't the player we have seen and there are questions whether or not he even wants to be here. Rutschman was also traded to the Boston Red Sox, and just like that, the face of the franchise was gone and so was the hope of Baltimore baseball. So, what happened in between those years, and what went wrong?

2019: Disaster but Hope on the Horizon

I'm not going to sit here and act like I was a fan who watched all 162 games of an MLB season no matter the outcome. That was not me in 2019. This year was an absolute disaster. Barely winning over 50 games and having guys like Rio Ruiz and Richie Martin as everyday players didn't exactly create much excitement or give me a reason to regularly watch this team.

This was also the year Chris Davis had his infamous hitless streak, going 46 at-bats and 62 consecutive plate appearances without a hit. For the record, I once had a hitless streak in Division III baseball of 21 consecutive at-bats, and I genuinely thought the world was ending. I can't imagine what the dude was going through while playing professional baseball and having that happen.

That's why it was hard not to smile and feel happy for the guy when he finally got his hit in Boston. Maybe after that he would go on some crazy hot streak and turn our season around! Nope. The highest-paid player in Orioles history at that point finished the year hitting .179 with only 12 home runs.

The silver lining of this season was having a few more wins than the previous year, a young rising star in Trey Mancini, and, of course, drafting our future franchise players, Adley Rutschman and Gunnar Henderson. Their selections gave every Baltimore Orioles fan a sense of hope for the future that very day.

2020: The COVID Year

Perhaps the most forgettable year, or unforgettable depending on how you viewed it, in MLB history took place in 2020 due to the pandemic. This was a shortened 60-game season, and the Orioles finished with a 25-35 record.

Oddly enough, I wasn't too upset about it because I still didn't have high expectations for the team. It was just... meh, whatever.

The Orioles drafted Heston Kjerstad with the second overall pick and continued to develop Grayson Rodriguez, one of the organization's top pitching prospects. Another young outfielder and the hope of a future ace gave the city even more reason to hang on for a few more years while waiting for the tides to turn.

2021: The Losses Continue, The Future Approaches

This was just another disappointing year. Perhaps even more disappointing than expected. The Orioles finished 52-110, which was the worst record in the American League and their fourth straight losing season. This season also included one of the lowest points in franchise history: the infamous 19-game losing streak in August.

I remember reaching the point where I almost wanted them to break the 1961 Phillies' MLB record of 23 consecutive losses just so there would be something memorable about this season. It was also the first year I truly questioned what the hell Mike Elias's strategy was. What was going on? When were we going to win some damn games?

But I kept telling myself that he had a plan and that I just needed to be patient. (I was an idiot.)

The Orioles used the fifth overall pick in the draft to select outfielder Colton Cowser, who at the time was another exciting young prospect. I began to see a real vision for what this team could become in the future. (Again, I was an idiot, and people who know me know there are few people in this world I despise more than Colton Cowser.)

2022: The Rebuild Takes Flight

For the first time in what felt like forever, Orioles baseball was fun again.

The Orioles finished the 2022 season with an 83-79 record, a stunning 31-game improvement over their 52-110 finish in 2021. The Orioles didn't make the playoffs, but they found a way to remain in the Wild Card race until the final week of the season, and they posted their first winning record since 2016. Man, this season was so much fun.

The rebuild was happening faster than I, and a lot of Orioles fans, had expected. On May 21, 2022, Adley Rutschman made his long-awaited major league debut. For years, Orioles fans had heard that Adley was the future of the franchise. Now he was finally here.

His impact quickly became obvious. The Orioles went 63-50 in games he played during the 2022 season, helping transform the club from a rebuilding team into a legitimate contender.

This was also the year we saw rookie closer Félix Bautista, aka "The Mountain," establish himself as one of the most dominant relievers in baseball. In his first season, he showed flashes of greatness, while Dean Kremer and Kyle Bradish demonstrated that they could be core pieces of our up-and-coming team.

We also experienced one of the most emotional moments of Orioles baseball in years when lifelong Oriole Trey Mancini was traded at the deadline. Mancini's final home at-bat as an Oriole resulted in an inside-the-park, game-winning home run. It was hard to find a dry eye at Camden Yards that day.

Looking back, 2022 was the year Mike Elias finally started to look like a genius instead of a mad scientist. The Orioles ultimately missed the playoffs, but that almost didn't matter. After years of being one of baseball's worst teams, they had become relevant again.

More importantly, the core was arriving. Adley Rutschman was in Baltimore. Gunnar Henderson made his major league debut late in the season, and the Orioles drafted yet another young, promising prospect with their 1st overall pick, Jackson Holliday. The farm system remained one of the best in baseball and only continued to look brighter.

For the first time since the beginning of the rebuild, the future wasn't something fans had to imagine. It was already on the field.

2023: From Contenders to Kings

Was This Actually the First Sign of Trouble?

If you have read this far, I have just rambled on and pretty much just given a summary of every year since 2019, and not actually my analysis of went wrong with this team as I said I would in the beginning of this. I will start this with the positives:

The Orioles won 101 games. Yes 101. Their best record since 1979 when they won 102 games. If 2022 was the year the Orioles became relevant again, 2023 was the year they announced to the baseball world that they had arrived. Coming off an unexpected 83-win season in 2022, many people expected the Orioles to take a step forward. Few expected them to become THE best team in baseball. For Orioles fans who had endured the brutal rebuild years, this season felt almost surreal. Just two years earlier, the club had lost 110 games. Now they were sitting atop the toughest division in baseball.

What made the 2023 Orioles special wasn't that they had a roster full of household names. It was that they found ways to win every type of game. They had timely hitting, a deep bullpen, strong defense, and contributions from seemingly everyone on the roster. Anthony Santander, Ryan Mountcastle, Cedric Mullins, Austin Hays, Kyle Bradish, and Félix Bautista all played key roles throughout the season. Team chemistry was exceptional, and for the first time in years, Orioles fans expected to win every night. The Orioles set an American League record by going 84 consecutive regular-season series without being swept, a streak that perfectly captured the resilience of this team. No matter how tough the opponent or how bad a game looked, the Orioles always seemed to bounce back.

Of course, no discussion of 2023 is complete without mentioning the ending.

After clinching their first playoff berth since 2016 and winning the AL East, expectations in Baltimore were sky high. Fans dreamed of a deep postseason run and perhaps even a World Series appearance. Instead, the Orioles ran into the eventual World Series champion Texas Rangers and were swept in three games in the ALDS. The magical season ended almost as quickly as it had begun. While fans were without a doubt devastated to how this season ended, I think everyone (including myself) recovered after a little and remained excited for the future of Orioles baseball.

However, what if I told you that looking at where the Orioles are today (August 25th, 2026), the signs for how where they are right now were there this very season.

For a front office that had spent years preaching patience, 2023 felt like the moment to push all the chips into the middle of the table. Instead, Mike Elias largely sat on his hands, like the absolute coward he is. At the trade deadline, Baltimore's headline acquisition was Jack Flaherty, a pitcher who struggled badly after arriving in Baltimore. To be fair, Flaherty wasn't having a "bad" year up to this point by any means. However, this just wasn't the splash move the fans were expecting, especially with proven postseason pitchers like Justin Verlander and Max Scherzer traded that same deadline. Rather than aggressively targeting impact arms or proven playoff contributors, the Orioles appeared content to simply make the postseason. For many fans, this was the first indication that Elias might be more comfortable accumulating prospects than taking risks to win a championship. While contenders around baseball strengthened their rosters, Baltimore made what looked more like a cautious move than a bold one.

At the time, it was easy to ignore because the team kept winning. They won 101 games. They won the division. They were young and appeared destined to contend for years. But baseball windows close faster than fans think.

The assumption was that Gunnar Henderson would keep getting better, Adley Rutschman would become an MVP candidate, the pitching prospects would develop, and the Orioles would have multiple opportunities to win a World Series. What nobody considered was that 2023 might have been the opportunity.

By the time the Orioles were swept by Texas in the ALDS, there was a growing feeling that they had missed a chance. The Rangers were aggressive. Baltimore was conservative. One team played like it was trying to win a World Series. The other played like it was hoping its future would eventually arrive.

The irony is that the future had already arrived.

At the time, the season felt like the start of a dynasty. In hindsight, it may have been the first warning that the one of the Orioles' biggest obstacles wasn't talent. It was an organization that seemed unwilling to act with urgency when the opportunity to win was staring it directly in the face.

2024: Doubt Creeps In

After winning 101 games and the AL East in 2023, expectations had changed. Nobody was talking about rebuilding anymore. Nobody was talking about the future. The future had arrived.

The Orioles entered 2024 as legitimate World Series contenders. And while I just spent a hot second complaining about Elias being a coward earlier, to his credit, he finally made a major move for what Baltimore needed. An ace. He acquired Corbin Burnes, giving Baltimore the true ace fans had been begging for. Burnes delivered exactly what was expected, helping anchor a rotation that spent much of the season battling injuries.

Despite significant injuries and some regression from the previous season, the Orioles still won 91 games, finished second in the AL East, and reached the postseason for the second straight year.

On paper, that sounds like a successful season. Yet 2024 is the year many Orioles fans began to feel uneasy.

For years, the rebuild was sold as a means to an end. The Orioles endured 115 losses, 108 losses, and 110 losses because someday the organization would have a young core capable of winning a World Series. By 2024, that core was fully assembled. Adley Rutschman was in his prime. Gunnar Henderson had become a superstar. Jordan Westburg was emerging. Colton Cowser arrived. Corbin Burnes gave the team a frontline ace. This was no longer a team hoping to compete someday. This was a team built to win now.

And that's what made the trade deadline so frustrating. While other contenders aggressively pursued impact players, the Orioles once again made moves around the margins rather than delivering the kind of blockbuster additions many felt the roster deserved. Our deadline consisted of Zach Eflin and Trevor Rogers. Eflin was a fine pitcher at the time, but nothing to write home about, and Rogers at the time was absolutely abysmal. In fact he was so bad, that we sent him down to Triple-A. It looked absolutely terrible at the time. (I digress now as he has proven he is a legit starter in my humble opinion). What this came down to for me was for a fanbase that had waited half a decade for contention, there was a growing sentiment that the front office remained more focused on protecting prospects than maximizing a championship opportunity.

Whether that criticism was fair or not, it became impossible to ignore after October.

Side note: I think this was the first year I really, and I mean really, was growing sick and tired of hearing the word "prospects". I think this started due to none other than Jackson Holiday. (I will get into more analysis with him in a bit) But I don't think there was a more anticipated debut from Orioles fans for Holiday since Adley in 2019. I remember his first game in Boston going to Chilis with my dad to watch it. (Chilis is spectacular btw). I already had Holiday's jersey before he step foot on an MLB field. I left the Chili's disappointed not by the food or vibes, that could never be the case, but because of Holiday's 0-4 performance. I thought to myself, whatever its his first game. What followed after that was pretty shocking if I am being honest. I will copy his stats below before he got sent back down to Triple-A:

• Games: 10

• At‑Bats: 34

• Hits: 2

• Batting Average: .059

• Runs: 0

• RBI: 0

• Stolen Bases: 0

• Home Runs: 0

Yea not what you want to see from your first-overall pick. From Wikipedia itself "This was the fewest hits by a No. 1 overall draft pick in their first 34 MLB at‑bats, and it marked the sharpest drop in batting average for any top‑pick since debuting in the majors"

But anyway, this is when I started to get bad vibes about our "prospects".

The Orioles entered the postseason and once again went out with barely a whimper, getting swept by the Kansas City Royals in the Wild Card Series. The offense was completely non-existent as Corbin Burnes pitched an absolute gem in game 1 but endured the loss in which would mark his final game as an Oriole. After being swept by Texas in the ALDS the previous year, Baltimore had now lost TEN, yes TEN, consecutive playoff games without a victory.

That is when many fans began looking back at 2023 differently. At the time, 2023 felt like the beginning of a dynasty. In hindsight, it may have been the first warning sign that talent alone wasn't enough. The Orioles had one of the best young cores in baseball, but championship windows don't stay open forever. Every year brings injuries, free agency, regression, and unexpected setbacks.

For the first time since the rebuild began, there was a growing fear that the Orioles were treating their championship window as if it would remain open indefinitely.

Maybe it would.

Maybe it wouldn't.

But one thing was becoming increasingly clear: winning 90 to 100 games in the regular season was no longer the standard by which this team would be judged. Not after everything fans endured to get here.

2025-Present: The Dynasty That Never Was

Earlier in this article, when discussing the 2023 season, I wrote:

"At the time, the season felt like the start of a dynasty. In hindsight, it may have been the first warning that the Orioles' biggest obstacle wasn't talent. It was an organization that seemed unwilling to act with urgency when the opportunity to win was staring it directly in the face."

Looking back now, I still believe there is plenty of blame to place on Mike Elias and the decisions made by this organization. In fact, I think this season has only strengthened my belief that the Orioles squandered precious opportunities when their championship window was wide open.

But there is one part of that statement I can no longer fully agree with.

I said the Orioles' biggest obstacle wasn't talent.

The more I reflect on what happened last season and what has unfolded since, the harder that becomes to believe.

Maybe the warning signs weren't just organizational. Maybe they were on the field all along.

For years, Orioles fans convinced themselves that the next prospect would solve everything. The next call-up. The next highly ranked farm system. The next wave of young talent. We were told this roster was overflowing with future stars and that a dynasty was around the corner. We believed it because we wanted to believe it. Now, standing here years later, I have to ask a difficult question:

What if the talent was never as special as we thought it was?

What if 2023 wasn't just the peak of the rebuild, but the peak of the roster itself?

Because when I look at this team today, I don't see a championship core that was held back solely by a cautious front office. I see a roster with glaring flaws, players who failed to take the next step, and a talent base that may have been significantly overrated by both the organization and its fans.

The painful reality is that the Orioles may have suffered from two problems at once. An organization that failed to act with urgency and a roster that ultimately wasn't talented enough to overcome those mistakes.

And if that's true, then the story of this era becomes even more disappointing. It wasn't just a championship window that was mishandled. It may have been a championship window that was never as wide open as we thought.

If 2024 raised questions, 2025 provided answers, and none of them were good.

The Orioles went from a 91-win playoff team to a 75-87 last-place team in the AL East. Brandon Hyde was fired in May, injuries piled up across the roster, and a team that had once looked like the future of baseball suddenly looked lost. Baltimore ultimately missed the postseason entirely after consecutive playoff appearances. 

For years, Orioles fans were told that the hard part was getting to contention. Once the team arrived, championships would follow. Instead, the exact opposite happened. The Orioles reached contention and immediately began moving backward.

Now in 2026, the Orioles have a new manager, Craig Albernaz, whom I am willing to give some leeway since it is his first year. However, I am not a fan of him whatsoever.

The guy just lacks a backbone, plain and simple. He spends more time talking about how much he loves the cities of our division rivals than showing any emotion when it comes to defending his own players. A perfect example was when he said it was "done the right way" while discussing Padres pitcher Ron Marinaccio intentionally drilling Gunnar Henderson late in a game.

I'm not a Major League Baseball player, and I never will be, but I played baseball for 20 years of my life. If I were Gunnar Henderson and heard my manager say that, I would have lost all respect for him in that moment.

And that brings me to my next concern with this team: Gunnar Henderson.

There is no doubt that Gunnar Henderson is a star in Major League Baseball... or is there?

That is a question I wish I knew the answer to.

He is currently having the worst season of his career, and it could not be happening at a worse time. The Orioles front office likely does not know what it wants to do with him long term, and time is running out on his rookie contract. There have been rumors circulating that, after Adley's departure, Henderson simply doesn't want to be in Baltimore anymore.

Whether there is any truth to those rumors, none of us truly know. But honestly, it is hard to blame him if there is. If Orioles fans have learned anything over the years, it is that developing and sustaining success in Baltimore often feels like an impossible task.

The same questions apply to Jackson Holliday.

Is he eventually going to become the superstar everyone envisioned? Truthfully, I don't know. He has shown flashes of brilliance and moments that remind you why he was considered one of the best prospects in baseball. However, his offensive and defensive inconsistencies still leave more questions than answers.

While I have spent a lot of time criticizing this team and pointing out its flaws, I would be remiss if I didn't acknowledge one of the few bright spots. Pete Alonso has been everything the Orioles hoped he would be and more. In a season filled with disappointment, he has consistently been one of the team's most productive and reliable players. Ironically, one of the franchise's biggest success stories has come from a player who wasn't developed by the organization at all.

As I write this, the Orioles remain just one game out of a Wild Card spot.

However, what separates me from some of my friends is that I do not have false hope (Shoutout Cole McGee).

Yes, the Orioles are only one game out of the Wild Card. But they are also still five games under .500. The American League has been incredibly weak this season, and it feels like nobody truly wants to claim that final playoff spot.

Don't get me wrong, I will never stop rooting for my team. If they somehow find a way to sneak into the playoffs, I will be right there cheering them on. Would it be fun? Absolutely.

But this team still has major issues, and the truth is that I do not believe they would make much noise once they got there.

More than anything, this season has reinforced a painful reality: I simply do not think we are going to see another Orioles team like the 2023 club for a very long time. That team felt like the beginning of something special. Instead, it may end up being remembered as the peak.

Conclusion: So What Went Wrong?

The easiest answer is to blame Mike Elias. Believe me, I have done plenty of that throughout this, and I still believe he deserves more blame than anyone for what this team has become. When the Orioles finally emerged from the darkness of the rebuild, Elias treated their championship window as if it would remain open forever. He protected prospects, avoided meaningful risks, and repeatedly operated with the caution of a general manager afraid to be wrong rather than the urgency of one determined to win.

But that is no longer the complete answer.

The Orioles did not fall apart because of one bad trade deadline, one disappointing free-agent class, one manager, or one postseason collapse. They fell apart because nearly everything that needed to go right eventually went wrong. The front office failed to surround the young core with enough proven talent. Injuries exposed a lack of depth. Highly regarded prospects did not always become the stars we were promised.

Established players regressed. The organization continued asking its own development system to provide every answer, even as the questions became increasingly difficult.

For years, Orioles fans were sold a vision. We were told to endure the losing because something extraordinary was being built. Every miserable season was supposed to be another brick in the foundation. Every high draft pick was supposed to bring us one step closer. Adley Rutschman would be the leader. Gunnar Henderson would be the superstar. Jackson Holliday would be the next great Oriole. The farm system would become an endless pipeline of talent, and once the team started winning, it would keep winning for years.

Then 2023 happened, and for one glorious summer, all of it appeared to be true.

The Orioles won 101 games. Camden Yards was alive again. The city believed again. It felt like the beginning of a dynasty, and perhaps that was the greatest illusion of all. We looked at an incredible season and assumed it was the beginning when, in reality, it may have been the peak.

That is what makes this entire era so painful. The Orioles did not fail because they never had an opportunity. They failed because the opportunity arrived, stood directly in front of them, and was treated like the first of many instead of the chance it actually was.

At first, I believed talent was never the problem. I believed this young core had simply been betrayed by a timid organization that refused to act with urgency. Now, I am forced to consider a more devastating possibility: maybe both things were true. Maybe the front office failed the players, and maybe the players were never quite good enough to overcome those failures. Maybe the organization overvalued its prospects while the fanbase overestimated the core. Maybe we were so desperate to believe the rebuild had worked that we ignored the warning signs until the window had already begun to close.

That does not mean these players were failures. It does not erase the joy they brought back to Baltimore or the memories of 2022 and 2023. It simply means that a collection of exciting young players is not automatically a championship team. Potential is not production. Regular-season success is not postseason success. A highly ranked farm system is not a trophy. At some point, an organization has to stop celebrating what its players may eventually become and start building around what they are right now.

The Orioles never seemed to understand that distinction until it was too late.

They kept waiting for the next prospect, the next breakout, the next season, and the next opportunity. They acted as though time was another organizational asset they could stockpile. But time does not work that way in baseball. Players get hurt. Careers stall. Contracts expire. Confidence disappears. Other teams improve. Windows that once appeared wide open can quietly close before anyone is willing to admit it. And now, the Orioles are left searching for answers that should have been found years ago.

I will always root for this team. That is the burden of being a fan. No matter how frustrated I become, no matter how many decisions leave me furious, and no matter how hopeless the future may occasionally feel, I will still turn on the game believing that this might be the night something changes.

But belief is no longer enough.

The Orioles spent years asking their fans to trust the process. We trusted it. We endured the losses, celebrated the prospects, filled Camden Yards when the winning returned, and convinced ourselves that the suffering had finally produced something built to last.

Instead, we may have witnessed the dynasty that never was.

So, what went wrong with the Baltimore Orioles?

They had talent, but perhaps not as much as we believed. They had opportunities, but failed to treat them with urgency. They had a championship window, but behaved as though it could never close.

By the time they realized they were running out of time, the time was already gone.