Pittsburgh Pirates, Ben Cherington, MLB DraftPittsburgh Pirates general manager Ben Cherington talks with reporters during Major League Baseball’s general manager meetings, Wednesday, Nov. 10, 2021, in Carlsbad, Calif. (AP Photo/Gregory Bull)

Major League Baseball’s Winter Meetings are upon us.

Front office executives, coaches, players and agents are convening in Orlando in what’s typically the busiest week of the offseason. There will be free agent signings, trades, tons of rumors and more with the baseball world all in the same place.

For the Pittsburgh Pirates, it could be a busier and more notable one than ever before. The Pirates aren’t usually known for offseason splashes, but there’s a heightened level of urgency this winter with a willingness to shop in a different aisle than usual. And there’s a lot to be done.

Here’s a rundown leading up to the the start of this week’s Winter Meetings.

Done Deals

Only one deal of note so far. The Pirates swung a five-player trade that sent starting pitcher Johan Oviedo, minor-league left-hander Tyler Samaniego and catching prospect Adonys Guzman to the Boston Red Sox for outfielder Jhostynxon García and pitching prospect Jesus Travieso.

It’s certainly an interesting deal for both sides. The Pirates traded from an area of strength to address a big need in getting García, who is a top 100 prospect with big time power potential. Looking at how the roster is currently constructed, García is penciled in as the team’s starting left fielder, but things could certainly change between now and Opening Day, which leads us to…

What’s Left to Do

Despite adding García, the Pirates aren’t ruling out adding another outfielder. The Pirates need to still add multiple bats this offseason. In addition to another outfielder, the Pirates could look to upgrade their offense in the infield.

They’ve been linked to a number of notable names in both free agency and on the trade market. Among the free agents Pittsburgh reportedly has interest in are Kyle Schwarber, Jorge Polanco, Kazuma Okamoto and others. They also have explored the possibility of trading for St. Louis Cardinals utilityman Brendan Donovan and New York Mets second baseman Jeff McNeil and make sense as a possible destination for a number of others who could be on the market.

Offense is they key priority for the Pirates this offseason, so much so that Ben Cherington might sign his first multi-year free agent. *Gasps*

But in addition to offense, the Pirates are looking for bullpen upgrades and could look to add starting pitching depth, especially if…

They decide to trade Mitch Keller. Even after trading Oviedo, there’s a chance Keller is move for an established bat before Opening Day. Trading Keller would be a risk but a deal could provide the typically-stingy Pirates with further financial flexibility.

If not Keller, the Pirates could still trade one of their young starters.

Miscellaneous

While there will be no shortage of deals and rumors this week, there are some other things to monitor during the Winter Meetings.

For starters, manager Don Kelly, after bringing on Bill Murphy as pitching coach, Kristopher Negron as bench coach and Tony Beasley as third base coach, is expected to add one or two more coaches to his staff.

Former Pirates outfielder Barry Bonds will find out if he gets inducted to the Hall of Fame on Sunday via the Era Committee. Bonds will need 12 votes from a 16-person panel to get in.

The MLB Draft Lottery will take place on Tuesday and the Pirates are once again in the running for the top pick. In fact, they have the third best odds (16.81%) to pick first in the 2026 draft behind only the Chicago White Sox (27.73%) and Minnesota Twins (22.82%). The last time the Pirates won the lottery they landed Paul Skenes. Not a bad choice.

The Rule 5 Draft is the most notable event of the final day of the meetings. The Pirates want to compete this year, so I don’t necessarily see them making a choice in the MLB-portion of the draft. Pittsburgh added a handful of players to their roster to protect them from being taken, but left-handed pitcher Anthony Solometo and catcher Omar Alfonzo are among the players at risk of being selected by other clubs.

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