The Status of the Pittsburgh Pirates Heading Into the MLB Winter Meetings

The Major League Baseball Winter Meetings begin next week, and this year will certainly be an interesting one to follow as free agency kicks in. I would expect teams to be very conservative with spending, considering the ongoing pandemic, the shortened 2020 season, and the financial impacts from both.

The Pirates have some needs, which we’ll break down heading into the meetings. Over the last month we’ve been looking at the whole organization, with recaps and looks forward on every position. Below you will find links to over 30 articles that I’ve written during that time, aimed at giving a complete look at where the organization stands going into the offseason.


Position Recap: Breaking Down How Jacob Stallings Became the Pirates’ Starting Catcher

Future Outlook: The Decline of the Catching Position Under Neal Huntington

Analysis: Jacob Stallings Can Handle Things Now, But the Pirates Need Future Catching Help

First Base

Position Recap: Which Josh Bell Will Show Up in 2021?

Future Outlook: Mason Martin, Will Craig, and the Future Battle For First Base in Pittsburgh

Analysis: Is Josh Bell a Pittsburgh Pirate After the 2021 Trade Deadline?

Second Base

Position Recap: What Should the Pirates Do With Adam Frazier This Offseason?

Future Outlook: The Pirates Have Plenty of Second Base Prospects, and One Chance to Be Above-Average

Analysis: A Future Infield You Can Build A Contender Around

Third Base

Position Recap: The Pirates Found a Player They Can Build Around in Ke’Bryan Hayes

Future Outlook: The Pirates Have Very Few Prospects at Third Base, But How Many Do You Need With Ke’Bryan Hayes?

Analysis: What Would an Extension For Ke’Bryan Hayes Look Like?


Position Recap: How Neal Huntington and Ben Cherington Rebuilt the Shortstop Depth in the Pirates’ System

Future Outlook: The Pirates Have a Bright Future at Shortstop, But Questions to Answer in 2021

Analysis: If You Could Only Have One Fielder, Where Would You Position Him?

Left Field

Position Recap: Breaking Down All of the Internal Options For the Final Pirates Outfield Spot

Future Outlook: The Outfield Prospect Depth in the Pirates’ System is Limited

Analysis: The Final Piece of Development

Center Field

Position Recap: Breaking Down How Bryan Reynolds Ended Up in Center Field For the Pirates in 2020

Future Outlook: Bryan Reynolds, Travis Swaggerty, and the Future of the Pirates in Center Field

Analysis: The Case For Bryan Reynolds in Center Field in 2021

Right Field

Position Recap: Signs of Hope and Reality For a Gregory Polanco Breakout in 2021

Future Outlook: The Best Future Spot For Oneil Cruz is in Right Field

Analysis: Speeding Up Bats to the Majors


Position Recap: Colin Moran Leads the Pirates Bench Options Who Could Start in the Future

Future Outlook: The Future Bench Options of the Pittsburgh Pirates

Analysis: Repairing a Broken Factory

Starting Rotation

Position Recap: Breaking Down the Pirates’ 2020 Rotation

Future Outlook: What Does the Future Pirates’ Rotation Look Like?

Analysis: What Does the Pirates Rotation Need in 2021?


Position Recap: The Relievers Who Can Help the Pirates in 2021

Future Outlook: The Pirates Have Hard Throwing Relief Prospects Who Are Used to Pitching Multiple Innings

Analysis: Traditional Bullpens Versus Modern Bullpens