The window to be a contender in baseball is finite, and because of the volatile nature of the game, a team that’s on top today could be facing a different reality tomorrow. As a result, when teams get the opportunity to capitalize on being one of the sport’s best teams, they have to seize their moment.
The Baltimore Orioles gave themselves the chance to do that over the past two seasons, winning more than 90 games and making the playoffs each year, but as this offseason progresses, they seem to be squandering their opportunity to get a leg up on the rest of the league.
For years in Baltimore, the Orioles had one model. Field competitive teams with star players such as Manny Machado, Nick Markakis or Zack Britton until a year or two before they hit free agency, and then trade those stars for younger players, keeping the payroll low. That model is similar to the one used by other small-market teams, including the Pirates, Rays and Guardians.
In this most recent rebuilding cycle — after 115, 108, 35 and 110 losses from 2018 through 2021 — the O’s stockpiled a considerable amount of talent, headlined by two No. 1 overall picks in Adley Rutschman and Jackson Holiday. They also drafted a number of other impact players, including shortstop Gunnar Henderson, third baseman Jordan Westburg and outfielder Heston Kjerstad.
Not only did the O’s strike gold with several of those players, but this team also ended up being the last to benefit from an era of roster construction in which teams could tank and be rewarded for it. Prior to the implementation of the draft lottery in 2022, baseball’s worst team by record received the first pick in the draft. The Orioles took advantage of that more than once and seemed primed for a lengthy window of contention once their rebuild came to fruition.
But with Baltimore having come up almost empty throughout free agency thus far, and with many of the top free agents this offseason now off the board, the Orioles appear to be falling back into their old habits — ones that were supposed to disappear once their talent level increased. This is a contending team still behaving like a rebuilding one. The roster has much of the foundation in place to be a perennial winner, but they have some key missing pieces that can only be addressed via trades or free agency.
The Orioles’ lack of aggressiveness when it comes to major free agents is particularly concerning considering that they have a new ownership group in David Rubinstein, who vowed to invest in the team, and the majority of their young talent is pre-arbitration, which makes now the perfect time for the organization to spend big on veteran free agents. What’s more, without some significant spending, it’s not clear how the Orioles plan to improve beyond the homegrown players currently on their roster.
For more than two seasons now, the Orioles’ biggest need has been top-tier starting pitching. They partially addressed that in February, when they acquired Corbin Burnes from the Brewers, adding him atop their rotation in his final season before free agency. But after a sensational year from Burnes, the O’s watched their former ace leave and head to the Diamondbacks on a nine-year, $210 million deal. Baltimore has also missed on other frontline starters this offseason, including Blake Snell, Max Fried and Garrett Crochet, who was traded to the division-rival Boston Red Sox.
Baltimore’s response? Signing 35-year-old Tomoyuki Sugano out of Japan. To be fair, Sugano could prove to be a worthy signing as a middle- or back-of-the-rotation arm, but this was not the big-time, impact move the Orioles needed. And while signing Tyler O’Neill to a three-year, $49.5 million deal is a nice addition in the outfield, that alone isn’t enough to carry their offseason.
Another area where it seems like the Orioles have taken missteps is their unwillingness to move the better prospects in their farm system. When teams are as bad as Baltimore was from 2017 to ‘21, it usually means big-time prospects entering their system, which is exactly what happened. And while some of those players have since become part of the roster at the big-league level, not all will reach the majors with the team that drafted them or signed them internationally.
Thus far, the Orioles have appeared to be unwilling to move prospects such as Kjerstad or catcher Samuel Basallo. Meanwhile, other top prospects such as first baseman Coby Mayo are positionally blocked at the big-league level. These are the young talents that Baltimore should be flipping for established big leaguers.
The one recent instance of Baltimore moving prospects in a deal was the trade of infielder Connor Norby and outfielder Kyle Stowers to the Marlins for left-hander Trevor Rogers at this past July’s trade deadline. That move did not pay dividends, as Rogers had a 7.11 ERA following the trade and was optioned to Triple-A Norfolk. The team failed to make any other significant moves at the deadline, finished second in the AL East and was swept out of the wild-card round.
No team is ever guaranteed a window to contend. And just because a team has what it believes are all the right pieces to succeed doesn’t mean things will work out the way they expect. Just look at the Chicago White Sox or the Toronto Blue Jays. A few years ago, both teams were young and fun and supposed to be up next. Neither lived up to those expectations.
Sometimes players get hurt; other times they regress and don’t develop into what they were expected to be. That’s just one more reason there has to be a balance among prospects, trades and free agents when it comes to building a winning roster.
The Orioles are no longer the new kids on the block looking to surprise the American League. They’re still young, talented and hungry, but they’re not sneaking up on anybody anymore. And after they were swept in the first round of the postseason in 2023 and ‘24, without any significant additions to their roster, there’s not much to give the Baltimore fan base hope that things will be different in the upcoming season.
Not to mention that at the time when it looked like the O’s were on the verge of taking the AL East by storm, the Yankees instead showed that they’re the class of the division. And now, coming off a trip to the World Series, the Yankees have been the division’s most aggressive team this winter and will be better in 2025 than the team that lost to the Dodgers. Also, the Boston Red Sox have improved significantly through upgrades to their rotation.
If the Orioles continue to be stagnant, they’re at risk of watching what they’ve built slowly fade away while the rest of their division and the American League pass them by.
