After an unprecedented summer, the Orioles head into an offseason that figures to be unlike any other. Following a 60-game season in which Baltimore outperformed expectations and welcomed several promising prospects, things are trending upward for the first time in a while. What happens this winter could determine whether the organization remains heading in that direction.

• Big questions facing the O's this offseason

Let’s break down what general manager Mike Elias and Co. will be up to in the coming months, and how it can shape the Orioles' future:

Which players are free agents?
The Orioles have two impending free agent: veteran lefty Wade LeBlanc and backup catcher Bryan Holaday.

Signed to a Minor League deal last offseason, LeBlanc earned a rotation spot and pitched to an 8.06 ERA before sustaining a season-ending stress reaction in his left elbow. The Orioles are not expected to pursue the 12-year veteran.

Expanded rosters allowed the O’s to carry Holaday, a nine-year veteran of five teams, for most of 2020. He hit .161 without a homer in 20 games, but was responsible for one of the defensive highlights of the season during a rare cameo at first base during his team debut on Aug. 1, when he improbably snagged a hard-hit liner that helped Baltimore to a 5-4, 11-inning win over the Rays.

Which players had options?
The only pressing option was José Iglesias' $3.5 million club option, which the Orioles exercised on Sunday. Iglesias was one of the club’s most productive bats last season, hitting .373 with three homers and a .956 OPS despite playing through various injuries. He also steadied the infield defense when healthy enough to play shortstop.

Who might be a non-tender candidate?
The Orioles trimmed their potentially large arbitration class with a flurry of in-season trades. As it stands, seven arbitration-eligible players remain: second-year eligible Trey Mancini and Hanser Alberto as well as first-timers Anthony Santander, Renato Núñez, Pedro Severino, Pat Valaika and Shawn Armstrong. No obvious non-tender candidates remain after the O’s designated for assignment Asher Wojciechowski last month.

But a few could force tough decisions. No Oriole has hit more homers over the past two years than Núñez, but he could be non-tendered given the size of the raise he might be in line for. The arbitration process tends to reward power and counting stats. With 43 homers and 121 RBIs since the start of 2019, Núñez may have made himself too expensive for the O’s taste. Armstrong is a potential candidate, too, after pitching to a 4.41 ERA in 65 appearances for Baltimore over the past two seasons.

Both are also trade candidates if they are tendered contracts, as is Severino.

When does the club have to make these decisions?
The non-tender deadline is Dec. 2.

When is the deadline for clubs and arbitration-eligible players to exchange salary figures?
Jan. 11, 2021

Who needs to be added to the 40-man roster this winter to avoid the Rule 5 Draft, and do they have a crunch for roster spots?
The Orioles have four prospects in their top 19 list per MLB Pipeline to protect: Outfielder Yusniel Diaz (No. 8), right-hander Michael Baumann (No. 9) and lefties Zac Lowther (No. 11) and Alexander Wells (No. 19). All should be locks to be protected when the time comes.

But they are also part of a larger-than-usual class of candidates that includes the almost-MLB-ready infielder Rylan Bannon (No. 25) and unranked relievers Isaac Mattson and Zac Pop. Mattson was acquired in the Dylan Bundy trade, while Bannon and Pop came over in the Manny Machado deal. Pop, 24, underwent Tommy John surgery in 2019 and should be healthy for the '21 season.

Keeping all of them will be a challenge: The O’s currently have four open 40-man spots, but they will need two to reinstate Mancini and Richie Martin from the 60-day injured list. Expect significant roster turnover in the coming weeks.

If so, how might that be resolved?
The Orioles protected four players from the Rule 5 Draft last winter; let’s conservatively say they protect five this year. That would require opening three spots, either through non-tenders, DFA or simply passing players with options through waivers.

Their roster is full of players they’ve either claimed off waivers or pushed through the process before, including six pitchers. It also consists of four catchers, which is probably one more than necessary. Players who seem particularly vulnerable at the current moment include Andrew Velazquez, David Hess, Austin Wynns and Cole Sulser.

When does that need to be set?
Teams must reinstate players from the 60-day IL by five days after the conclusion of the World Series. The deadline to protect prospects from the Rule 5 Draft is Nov. 20.

What kind of help do they need and will they be active in free agency? Who might they target?
Still in rebuilding mode and facing uncertainty on the financial side, the Orioles are not expected to be major players in free agency. There is a chance they could scour the lower tiers of the starting-pitching market for veteran depth, like they did last winter. But besides that, it should be another quiet winter in Baltimore on the free-agent front.

Any other housekeeping?
Two vacancies exist on the Major League coaching staff, since the club decided not to renew the contracts of pitching coach Doug Brocail and third base/infield coach Jose Flores. The possibility exists though that the Orioles could replace only Brocail and reduce their big league staff from eight to seven, perhaps by allocating some of Flores’ duties to MLB field coordinator Tim Cossins. Fredi Gonzalez is reportedly a candidate for the Tigers’ managerial opening and would open another vacancy should he leave for that job.

The O’s also recently cut ties with six Minor League instructors, including coaches Sean Berry and Butch Davis and pitching rehab coordinator Mike Griffin. It is unclear at the moment how many of those positions will be refilled, given the uncertainty surrounding the Minor Leagues at the moment. It is likely they at least find a replacement for Berry, who was the hitting coach at Triple-A Norfolk.