The offseason is underway, and it will be a pivotal one for the Orioles’ future.

Despite their regular-season success the past two years, the Orioles have struggled to get over the hump in the playoffs. Each of the past two seasons have ended in October sweeps, raising questions about what the club needs to take the next step.

Baltimore has five players who are free agents and three times as many who are eligible for arbitration. On top of those decisions, general manager Mike Elias must decide where to spend his money this winter now that he presumably has more of it with owner David Rubenstein at the helm.

Ahead of free agency beginning Monday, Baltimore Sun beat reporters Jacob Calvin Meyer and Matt Weyrich and editor Tim Schwartz give their thoughts on what this winter should look like for Baltimore.

What should be the Orioles’ top offseason priority?: Meyer: There are plenty of needs on this roster. The Orioles will enter the offseason with an ace-sized hole in their rotation, a 44-homer-sized hole in their lineup and a bullpen that needs revamping. How Elias goes about filling those holes is pivotal for the club’s success in 2025, but those matters are trivial in comparison with what should be atop Elias and Rubenstein’s to-do list: Sign Gunnar Henderson to a long-term contract extension. That, of course, is easier said than done, which is why I get paid what I get paid and Elias and Rubenstein get paid what they get paid. The Orioles have plenty of time before Henderson reaches free agency following the 2028 season, but at the very least there should be serious attempts made this offseason to lay the groundwork. The superstar shortstop also chose mega-agent Scott Boras to represent him, and while some Boras clients have signed extensions, they’re more likely to wait for free agency. But if Henderson — perhaps the best Oriole since Cal Ripken Jr. — is wearing Yankee pinstripes or Dodger blue in five years, it will be a disservice to a fan base that endured 14 straight losing seasons followed by one of the most ignominious rebuilds in MLB history.

Weyrich: Corbin Burnes is set to be a free agent and the Orioles, whether they retain him or not, must decide how they’re going to fill that void. Zach Eflin and Grayson Rodriguez will be back, but Kyle Bradish and Tyler Wells won’t be ready to return from their respective Tommy John elbow surgeries until the second half at the earliest. That leaves Dean Kremer, Albert Suárez and Cade Povich as the top candidates to fill out their rotation with Triple-A arms Trevor Rogers, Brandon Young and Chayce McDermott providing depth. It’s enough pitchers to break camp with a full roster, but the lack of a true workhorse starter poses questions over their ability to absorb injury. Eflin, despite being a nine-year MLB veteran, has never pitched more than 177 2/3 innings in a season. Rodriguez and Kremer both spent significant chunks of 2024 on the injured list, Suárez is heading into his age-35 campaign and Povich is still building up his arm for a full-season workload. As last season showed, there’s no such thing as too much pitching depth and the Orioles need a starter they can rely on to start every five days even if they don’t shop at the top of the market for an ace.

Schwartz: It has to be finding a new ace to lead the starting rotation. The trades for Corbin Burnes and Zach Eflin proved to be home runs, but Burnes is now a free agent and Eflin is not an ace — he’s probably a better No. 2 or 3. Bradish is coming off Tommy John elbow reconstruction and Grayson Rodriguez still needs to prove he can stay healthy and become that dominant starter. Elias will need to make more difficult decisions to find his new top-of-the-rotation starter, and the trade capital he had in January to make the move for Burnes has thinned significantly. Will new ownership pony up to pay Burnes $200 million or sign someone like Blake Snell? That’s the question every Orioles fan wants to know, and it will be the key to determining how serious to take this team’s playoff chances in 2025.

Should the Orioles re-sign Anthony Santander?: Meyer: In honor of it being election season, I’m going to dance around this question and not actually answer it. Should the Orioles give tons of money to a slugger who just put up one of the greatest power seasons from a switch-hitter in MLB history? Yes. Should the Orioles give tons of money to a player who hasn’t eclipsed 3.0 wins above replacement (by Baseball-Reference’s estimation) a single time in his career? No. Should the Orioles give tons of money to a hitter who carried their offense on his back in the second half? Yes. Should the Orioles give tons of money to a 30-year-old outfielder who is a below-average defender? No. This is complicated, and maybe it’s best to let the market dictate this one. If another team is willing to give Santander a seven-year, $150 million deal — the contract that The Athletic’s Jim Bowden, a former MLB general manager, predicted — it would be a surprise for Elias and company to match that. But if Santander’s deal is more reasonable — say, $80 million over four years — it makes sense for the Orioles to bring back a team leader, a fan favorite and his 44 homers.

Weyrich: Let’s consider the pros and cons. If Santander walks, they free up $11.7 million in payroll space and, after making him the qualifying offer, obtain a draft pick when he signs elsewhere. Heston Kjerstad finally has a path to regular playing time after posting a .746 OPS over 52 games the past two seasons. The Orioles would still need to find a right-handed corner outfielder to balance out the left-handed Kjerstad, Cedric Mullins and Colton Cowser, but they have the framework in place for life without Santander. However, by keeping him, the Orioles would retain a switch-hitting outfielder who’s blasted 105 home runs over the past three seasons — second most in the American League over that span behind only Aaron Judge. Though advanced metrics paint Santander as a below-average defender in right field, he plays deep in the outfield to keep the ball in front of him and limit mistakes and he has a strong enough arm to stick there for a few more years. He’s also a respected veteran leader for a still-young clubhouse and, should he command a significant raise in salary as expected, the Orioles appear to have the financial flexibility under first-year owner David Rubenstein to remain aggressive in improving their roster elsewhere with Santander on the books. The verdict? Sign the man who just carried your offense in the second half.

Schwartz: No. He’s going to be expensive, and the Orioles have an internal candidate — Kjerstad — who deserves a shot. If the Orioles are going to spend money, I would be surprised if it’s at a position where they already have an obvious replacement. That’s not to say keeping Santander would be a bad move; he’s perhaps still getting better and mashes in the heart of their lineup. But the Orioles have more important needs on the pitching staff, and that’s where they should focus their spending.

What type of starting pitcher should the Orioles sign?: Meyer: In his six offseasons as Orioles GM, Elias has not signed a single free agent to a multiyear major league contract. That could (and probably will) change this winter. With Rubenstein’s deeper pockets and ambition to actually win a World Series, Elias should be able to navigate the starting pitching market at all levels. Signing one of the top names — Burnes, Max Fried and Blake Snell — might be difficult considering they’ll all command nine-figure contracts, especially Burnes, who is expected to garner more than $200 million. It might not be in the cards for Baltimore to sign a bona fide ace, but that doesn’t mean Elias will have to take the Jordan Lyles/Kyle Gibson approach as he did before 2022 and 2023. There are plenty of starting pitchers in the middle of the market who make sense for the Orioles: left-handers Sean Manaea, Yusei Kikuchi and José Quintana; and right-handers Michael Wacha, Nathan Eovaldi and Luis Severino. All of those pitchers are expected to sign two-to-three-year deals in the range of $12 million to $22 million per year. It won’t be as splashy, but adding one of those names to a group that includes Zach Eflin, Grayson Rodriguez and Dean Kremer forms a good enough rotation before the injured Kyle Bradish potentially returns in the summer.

Weyrich: I touched on this in an earlier answer, but the Orioles need a workhorse. Burnes was both an ace and an innings-eater, a combination that will be tough to replace if they don’t set some team records and sign him in free agency. Though the Orioles could use an ace as much as any contender, they could afford to wait until midseason to trade for one when they have more clarity on Bradish’s timeline. But to get there, the Orioles will need another reliable starter to lean on. In today’s era of rampant pitching injuries, 180 innings is the new 200. Only three soon-to-be free agents hit that mark in 2024: Burnes, Luis Severino and Sean Manaea (expected to decline player option). Max Fried, Yusei Kikuchi and Nathan Eovaldi (player option) also came close. Burnes and Fried might prove too expensive for Baltimore, but the others could make a lot of sense as dependable starters with some upside for the Orioles to target this offseason.

Schwartz: How about the guy they had lead their rotation in 2024? Burnes fit like a glove in Baltimore, and aside from a rough August was as consistent as they come. Yes, his age is a concern, and the team that signs him is unlikely to like that deal in four or five years, but the Orioles’ window to win a World Series is wide-open, and they need a true ace to take them there. They lack a prospect that can develop into that, too. Bringing back Burnes solves their most glaring issue and also would prove to fans and other players around the league that Baltimore is, in fact, willing to spend money.

Which arbitration-eligible player offers the most interesting decision?: Meyer: Last year, the Orioles tendered contracts to all 17 of their arbitration-eligible players. Doing the same with their 15 such players this year would be a surprise. Of the 15, fewer than 10 are locks to be tendered contracts. That means the futures of Cedric Mullins, Jorge Mateo, Matt Bowman, Ramón Urías and Emmanuel Rivera and perhaps others are in question. What the Orioles do with Mateo, who missed the final half of the season with a dislocated elbow, is an interesting decision that could illustrate how the club plans to shape its 2025 roster. Mateo was billed as a super utilityman this past spring, but he mostly played second base after Jackson Holliday struggled in April. If the Orioles do hang onto Mateo, who MLB Trade Rumors projects for $3.2 million in arbitration, 2025 could be the year he actually serves as a Swiss Army knife who can play multiple infield and outfield spots.

Weyrich: Ryan Mountcastle is projected by MLB Trade Rumors to command $6.6 million this offseason, second only to Cedric Mullins ($8.7 million) among their arbitration-eligible players. The Orioles will first have to decide on Ryan O’Hearn’s $8 million team option, which could leave Mountcastle as the only proven starting first baseman on the roster. The presence of top prospects Coby Mayo and Samuel Basallo, both of whom have played first in the minors, could prompt the Orioles to explore trading Mountcastle, whose profile as a pull-heavy, right-handed power hitter hasn’t been a great fit in the spacious Camden Yards. The problem there is twofold: Mountcastle is one of the Orioles’ best hitters against left-handed pitching and Mayo’s first taste of the majors in 2024 left much to be desired. The Orioles might need to re-sign Santander or acquire a right-handed hitter of his caliber to justify a trade of Mountcastle, who is under team control through 2026. Doing so would be a bet on Mayo’s upside, which remains as high as any prospect in baseball, coming to fruition next season.

Schwartz: Mountcastle. The Orioles need a place for Coby Mayo in their lineup, and first base feels like the most obvious spot for him. And if Mayo doesn’t turn into the middle-of-the-lineup bat he projects to be, Basallo is the next guy up, and he would also need a place to play.

What will the Orioles’ opening-day payroll be, and where will it rank in MLB?: Meyer: $125 million — 22nd in MLB

Weyrich: $114 million — 20th in MLB

Schwartz: $131 million — 18th in MLB

Who is a free agent the Orioles will sign, and how much will they pay him?: Meyer: LHP Yusei Kikuchi — two years, $32 million

Weyrich: LHP Sean Manaea — three years, $63 million

Schwartz: RHP Corbin Burnes — six years, $200 million

What team will sign Juan Soto, and for how much will he sign?: Meyer: New York Mets — 15 years, $1 billion

Weyrich: Washington Nationals — 15 years, $600 million

Schwartz: New York Yankees — 14 years, $800 million