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Pirates Winter Meetings Preview: Storylines to Follow After Quiet Start to Offseason



Pittsburgh Pirates, Ben Cherington

Front office executives across the league are joined by players, agents, coaches and members of the media for the busiest week of Major League Baseball’s offseason. The 2023 Winter Meetings officially get underway at the Gaylord Opryland Resort & Convention Center in Nashville, Tenn.

For the Pittsburgh Pirates, there’s plenty of work to be done and plenty of storylines to follow.

It’s been a quiet offseason so far in Pittsburgh. The Pirates executed an early trade when they sent right-hander Cody Bolton to the Seattle Mariners for cash considerations. On Friday, the Pirates signed catcher Ali Sánchez to a one-year contract for 2024.

At some point this winter, the Pirates will have to make more impactful moves. The club has obvious needs that need addressed and are exploring both free agency and the trade market to remedy their deficiencies.

Here is everything to follow regarding the Pirates at this year’s Winter Meetings.

Starting Pitching, Starting Pitching And More Starting Pitching

Look at the current projections for the Pirates’ starting rotation. It’s off to a good start with Mitch Keller. After that, it consists of unknown.

As it currently stands, the Pirates would be looking at an Opening Day rotation of Keller, Bailey Falter, Luis Ortiz, Roansy Contreras and Quinn Priester. Keller was an All-Star last year. Falter (5.36 ERA), Ortiz (4.78), Contreras (6.59) and Priester (7.74) all struggled during their time with Pittsburgh in 2023.

The Pirates will need to add multiple starting pitchers this winter — at least two — and could look to strike in Nashville.

On the free agent market, names such as Sean Manaea, Michael Lorenzen, Frankie Montas, Michael Wacha and Jack Flaherty could be of interest. On the trade front, a trade for someone like Dylan Cease is probably unrealistic. However, someone such as the Oakland A’s Paul Blackburn presents a more reasonable option.

Who’s On First?

The Pirates will also need to address first base heading into next season. Carlos Santana spent the first half of the season their with the Pirates, but was traded to the Milwaukee Brewers at the trade deadline.

The 37-year-old performed well on both sides of the ball last season. He’s a free agent again this winter and is a candidate to return to the Pirates for a second-consecutive winter.

Among the other first baseman on the free agent market include Rhys Hoskins, Brandon Belt, Joey Votto, Rowdy Tellez and Dominic Smith.

22 Back For ’24?

It’s been widely speculated that Andrew McCutchen and the Pirates would re-up on another deal for 2024, yet no deal has happened.

McCutchen signed a one-year, $5 million deal last offseason to return to play for the Pirates for the first time since 2017. McCutchen was a solid contributor in his role as designated hitter last season and was praised for his veteran leadership. His season was ultimately cut short due to an Achilles injury.

Regarding a reunion for next season, it still feels more like a matter of when rather than a matter of it, though it is somewhat baffling there hasn’t been an agreement yet.

MLB Draft Lottery

For a second-straight year, the Pittsburgh Pirates are in the mix for the No. 1 overall pick through the draft lottery. Last year, the Pirates were tied for the best odds to land the pick and did so in the first-ever lottery.

This year, the odds are stacked against the Bucs. The Pirates have a three-percent chance to see their name attached to the No. 1 pick. Seven teams have a better chance. The Athletics, Royals and Rockies all have an 18.3% chance to pick first.

The draft lottery takes place at 5:30 p.m. ET on Tuesday night.

Rule 5 Draft

The Rule 5 Draft is the final set event of the Winter Meetings and will take place on Wednesday.

Last year, the Pirates selected left-handed pitcher José Hernández from the Los Angeles Dodgers’ organization. Hernández met all the necessary qualifications for a Rule 5 draftee and is still with the Pirates.

Pittsburgh Pirates general manager Ben Cherington could again look to make a selection. Earlier in the offseason, Pittsburgh Baseball Now looked at a player who could be of interest to the Pirates.

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