This story was excerpted from Jake Rill¡¯s Orioles Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.

BALTIMORE -- Last year,?Mike Elias?and members of the Orioles¡¯ front office traveled to San Diego for the return of the in-person Winter Meetings. It brought a much different experience for the general manager and his staff than earlier in his tenure.

Baltimore was no longer in the infant stages of its rebuild. Coming off an 83-win 2022 campaign, the O¡¯s were prepared to contend in the challenging American League East. They used the Winter Meetings to meet with agents and hold Zoom calls with big league-caliber free agents.

Elias was focused on trying to improve the Orioles¡¯ roster with the club in win-now mode. Players expressed a stronger interest in coming to Baltimore, realizing the team was on the rise.

On Sunday, Elias and his staff will arrive in Nashville, Tenn., for the?2023 Winter Meetings?with a better idea of what to expect while representing a contending team. They¡¯re again set on finding ways to immediately upgrade the Orioles, the reigning AL East champions fresh off a 101-win showing that should make them?quite appealing to players on the open market.

Here¡¯s everything O¡¯s fans need to know as this year¡¯s Winter Meetings get underway.

Key events
? Sunday, Dec. 3:?Hall of Fame?Contemporary Era ballot?results released (Cito Gaston,?Davey Johnson,?Jim Leyland,?Ed Montague,?Hank Peters,?Lou Piniella,?Joe West?and?Bill White)
? Tuesday, Dec. 5:?Draft Lottery
? Wednesday, Dec. 6:?Rule 5 Draft

Club needs
The Orioles have two primary needs: a starting pitcher who can upgrade their rotation and a closer who can fill in for?F¨¦lix Bautista?(out for the 2024 season after?Tommy John surgery).

At the General Managers Meetings in early November, Elias stated his intent to acquire a starter who can ideally slot into a top-three spot in Baltimore¡¯s rotation. The O¡¯s could get outbid on the free agent starting-pitching market, so they may need to swing a trade to land their ideal target.

The back end of the Orioles¡¯ bullpen needs to get stronger, and Elias is hoping to bring in a reliever with closing experience. Such a move could help offset the loss of the All-Star Bautista, who was the winner of the?2023 Mariano Rivera Award?as the AL¡¯s top reliever.

Potential trade candidates
Baltimore could look to move a veteran outfielder to clear room for several of its top prospects. Anthony Santander has been a popular name in trade rumors in recent offseasons, and the 29-year-old is projected to make $12.7 million in arbitration per MLBTradeRumors.com. That would make him the highest-paid O¡¯s player since Elias became GM in November 2018.

Santander is entering the final year of his contract, which could make him an ideal trade chip.

It¡¯s also possible the Orioles could deal a package of position-player prospects to acquire a top starting pitcher. Infielders Joey Ortiz (Baltimore¡¯s No. 6 prospect per MLB Pipeline) and Connor Norby (No. 7) may be among the youngsters the club could be willing to trade.

Prospects to know
Jackson Holliday, who turns 20 on Monday, is already on the cusp of the big leagues. MLB Pipeline¡¯s No. 1 overall prospect played at all four full-season Minor League levels in 2023, finishing the year with an 18-game stint at Triple-A Norfolk. The infielder is on track to make his MLB debut in ¡®24, and he could even make the team out of Spring Training.

Outfielders Colton Cowser (O¡¯s No. 2 prospect) and Heston Kjerstad (No. 3) each made his big league debut in 2023, and both could make their first Opening Day roster in ¡®24.

Baltimore likely won¡¯t want to block its top three prospects with any of its offseason moves.

Rule 5 Draft
The Orioles have selected at least one player during the Major League portion of every Rule 5 Draft since 2006, so expect them to use the No. 29 overall pick on Wednesday. Their 40-man roster has only 36 players heading into the Winter Meetings.

Outfielder?Hudson Haskin?(O¡¯s?No. 17) is the only one of Baltimore¡¯s top 30 prospects who is eligible to be taken by another team in the Rule 5 Draft.

Burning question
Some expected the Orioles to either sign a marquee free agent or pull off a blockbuster trade last offseason, and neither happened. Their primary acquisitions were right-hander?Kyle Gibson, lefty?Cole Irvin, infielder?Adam Frazier?and backup catcher?James McCann.

The big question: Will Baltimore make a bigger splash this winter?

If the O¡¯s decide to sign a top free agent pitcher (such as starter?Eduardo Rodriguez?or closer?Josh Hader) or land one of the top trade targets (like White Sox righty?Dylan Cease), it may not happen this week. Elias said last year that he primarily uses the Winter Meetings as an ¡°information-gathering event.¡±

But even if the Orioles¡¯ front-office staff leaves Nashville without a new big-name pitcher in tow, perhaps the club will make an aggressive move to upgrade its staff later in the offseason.