Two full seasons into their organizational rebuild, the Orioles enter the offseason at an inflection point.

It’s not make or break time yet, and 2020 was far from a perfect season. But flashes of what a winner could look like in Baltimore again were plain to see. What happens next could decide whether that comes to pass.

“It’s very difficult for me to label any season a success where we have a losing record, but I see enough positive things where we can feel good that this year was far from wasted and there was progress made toward our ultimate goals,” general manager and executive vice president Mike Elias said. “We feel despite the circumstances we managed to make the progress in our plan that we wanted to see.”

Here are five questions Baltimore now faces heading into the winter:

1. What to do with Chris Davis?
An annual topic of debate and discussion comes into heightened focus this winter. Why? Davis wasn’t just bad again in 2020. He was a non-factor, relegated to a bench role early and limited to 16 games due to unproductivity and knee issues. He has two years and upwards of $46 million remaining on his albatross contract, which O’s brass remains publicly committed to.

• Elias on Davis' future with Orioles

The difference now is, for the first time in years, Davis isn’t just occupying a roster spot. He’s sucking up at-bats that could be given to others. The O’s are staring down an upcoming logjam at first base/corner outfield, assuming Trey Mancini (colon cancer) and Anthony Santander (oblique) return healthy in 2020, Ryan Mountcastle remains a priority and Renato Núñez and others needing at-bats. Is this the offseason where they cut ties? Or does Davis remain in the fold?

2. How to handle the top prospects?
One consensus: The Orioles’ farm system is much improved. What was a bottom-third system when Elias arrived is now ranked No. 8 by MLB Pipeline, headlined by top prospect Adley Rutschman and enviable pitching depth. The first real wave arrived in 2020, with Mountcastle, Dean Kremer and Keegan Akin enjoying impressive debuts. The next appeared on the horizon for 2021, when Rutschman, DL Hall and many others seemingly on track to arrive had these been normal times.

• O's prospect report from alternate site

But things weren’t normal this year. Ten of the O’s top 15 prospects spent at least some time at their alternate training site in Bowie, Md., this summer, but few played competitively with no Minor League season. What does that mean for their development?

Holding instructional camp at the club’s Sarasota complex should help the bundle of college players the O’s drafted in 2020, many of whom haven’t played competitively otherwise since the spring. But questions remain about how to properly evaluate and place those prospects next year, given how the Orioles aren’t even sure what the Minor Leagues will look like next season from a structural standpoint.
“It’ll be totally case by case,” Elias said “We’re already having those discussions. If you were at Bowie all year, that’s a factor. Your age is a factor. I think we’re going to see a whole spectrum of outcomes there in terms of people skipping levels or repeating them.”

3. Which breakouts were real?
The evaluation challenge front offices face given 2020’s 60-game sample was on display recently, when manager Brandon Hyde was asked about his catching tandem of Pedro Severino and Chance Sisco. Both young players showed well early but faded down the stretch after hot starts.

“Three weeks ago they were 1.000 OPS players, and they both had a rough couple weeks,” Hyde said.

Exactly. But a couple weeks in 2020 can mean half the season.

Severino had a .885 OPS over his first 28 games and a .438 mark over his final 20. Sisco had a .886 OPS in Aug. and a .513 OPS in September. John Means had an 8.59 ERA through August and 2.48 ERA down the stretch. Tanner Scott broke out over 25 games, but what would the next 25 have looked like? Austin Hays was a roughly league-average offensive player in roughly the same sample he was an elite one for last September.

The list goes on and on. The question is: Which numbers do the O’s consider reflective, which do they consider mirage and how does that affect the decisions they make on those players going forward?

4. Who is part of the future? Who isn’t?
This is related to the last question, but it pertains more to the players who more or less matched their 2019 production for better or worse. Given the aforementioned position logjam, was Núñez’s streaking slugging worth the raise he’s due in arbitration? How about Hanser Alberto’s energy but low-slug production, now that he’s about to get more expensive as well? Is Rio Ruiz still developing? Can Mancini return healthy? Etc.

5. What’s the direction?
This might seem obvious on paper. The O’s have made no secret about leaning into their long-term goals since Elias, Hyde and Co. arrived in Baltimore. Which is why it was strange to hear Hyde declare he was in “win-now mode” come late August, with the O’s two games below .500 and already 4 1/2 games back in the Wild Card chase.

Consider it more a motivational tactic than reflective of any organizational riff. But the remarks did clash with what the front office has preached with both its words and wallet over the past two years. And by season’s end, you could make the case the Orioles actually overachieved in 2020, since the '21 Draft order is determined by final record. The O’s will draft fifth as a result, behind three other rebuilding clubs and the division rival Red Sox, who won a World Series as recently as 2018. Baltimore ended up 10 games below .500 and seven games out of the postseason.