This winter has been one of the busiest for the Pirates in quite some time.

So far, they have signed four free agents to major-league deals (first baseman Carlos Santana, catcher Austin Hedges, lefty reliever Jarlin García, starter Vince Velasquez) and picked up a couple more players via trade (first baseman Ji-Man Choi from the Rays, first baseman/outfielder Connor Joe from the Rockies and right-hander Dauri Moreta from the Reds). They may not be the flashiest of moves, but unlike past years where most of the notable transactions were trading away established big-leaguers, this year has focused more on improving the major-league team.

And they may not be done.

"Don't feel like it's a ‘have to,’ but certainly [we] want to do more," Ben Cherington said over Zoom. "Specifically, we would still like to add a starting pitcher. That market’s been strong, but we continue to stay engaged with some free agents and trade opportunities. Both of those can be hard to speculate, in terms of how likely it is to line up, but we would still like to add another starting pitcher to our group.

"We’d also like to add another position player, if we can. Another potential option for the lineup. We want to continue to lengthen that out. We feel good, if the season started tomorrow, with our position player group. We’ve got 13 guys, assuming that's what we start with. We feel good about putting together some combinations at different positions. But in a perfect world, we would we would still add to that group so we'll stay engaged on that."

Adding to the rotation has been a priority this offseason, with Cherington telling DK Pittsburgh Sports at the general manager meetings at the onset of the offseason that the Pirates could add multiple starting pitchers. Velasquez has a rotation spot secured going into spring training, and it is safe to assume that Mitch Keller, Roansy Contreras and JT Brubaker will return to the rotation as well. Another free agent signing could potentially force Johan Oviedo out of the opening day starting five, not to mention put the starting futures of pitchers like Bryse Wilson and Zach Thompson into question.

According to a source, the team has a minor-league deal with veteran right-hander Tyler Chatwood, though it appears to be more of a depth signing rather than the extra rotation arm Cherington alluded to.

The trade market may end up being the more appealing option to pick up that extra starter. If that happens, the outfield could potentially be an area where the Pirates pull from for a deal since they have plenty of depth.

"It's possible. Anything’s possible," Cherington said. "I think if you're going to add a starting pitcher through trade, we're gonna have to give something up. If there's areas we feel are deeper than others, that would make sense to look at. I’m not saying that to predict anything, because there may be other ways to go. The outfielders we have on our 40-man, there’s certainly some of them we feel, either either because of injury last year, or because there's still some skill development to do, that there’s still valuable time (needed) in Triple A for some of (the guys in) that group. We'll get into spring training and see where guys are. I think we certainly have lots of playing time between the big leagues and Triple A for everybody in that group."

While it is far from guaranteed to happen, the idea that the Pirates could start moving players from an area of depth to acquire an area of need does seem to signal a bit of a change in organizational strategy, going from prioritizing acquiring a mass of young talent first and dealing with the implications to the major-league club second. Ideally, it's a sign that they feel confident internally that they are improving.

“I think we’re deeper and that’s for a combination of reasons. One is that our young player group will continue to mature as we move into next year. When we’re in spring training and moving into April, our group of players compared to a year ago will be one year further ahead in their maturation and development, so that’s one reason why I think we’re deeper. We’ve been able to add to the team and hope to continue to add to the team externally to get deeper."

MORE PIRATE NEWS

Oneil Cruz has been sidelined from Winter Ball this week with what his winter team classified as a day-to-day injury, reportedly with his left ankle. Cherington doesn't believe it's going to have an impact on him getting ready for the 2023 season.

“He does have some swelling. He’s not going to play right now and let that calm down,” Cherington said. “I think given the holidays, we're going to look to try to get him to the States after the holidays just to be very sure about what's going on. But all reports so far are that it’s a relatively minor thing. It should pass without being too much of an issue.”

• On Tuesday, the Pirates designated Diego Castillo for assignment to make room for free agent signing Austin Hedges. Castillo was the pick because the Pirates have added several right-handed multi-positional players to their 40 man roster over the past few months, including Jared Triolo, Miguel Andujar, Connor Joe and Ryan Vilade.

"There's a number of right-hand-hitting multi-position players on the team and that made us feel Diego’s opportunity wasn't going to be as good going forward as it maybe had been coming into last year. It was a matter of our roster changing over 12 months, and the opportunity for him not being as good. We needed a spot and, relative to other things, we felt like this was the right way to go. We’ll see what happens next few days."

Earlier this offseason, the Pirates designated Hoy Park for assignment and eventually traded him to the Red Sox, meaning that if Castillo doesn't sneak through waivers, they'll have nobody left from the Clay Holmes trade they made in July 2021. That trade has bit the club, as Holmes emerged as an All-Star with the Yankees this past year.

"It was already hard. We look back on everything we do and the decisions we make and whether they go well or not we're going to learn from them. That's one certainly I spent a lot of time looking back on. I’m happy for Clay because he's a terrific guy and he's doing really well. At the time, we thought that deal made sense (because it) was an opportunity to get two position players we liked. As it turns out, that one hasn't hasn't worked out the way we hoped it would."

• The Pirates could add another starter or pitcher, the Pirates still are projected to be among the bottom of the league in player payroll. That gap is only getting larger this winter where teams like the Mets and Yankees have signed multiple players to nine-figure contracts.

"I said before and I’ll say again, we’ve got the resources here to win and we need to execute in baseball operations at a high level to do that," Cherington said. "We know that. Beyond that, the question about payroll size is sort of, kind of out of my hands, really, in terms of what different markets can do so we just don’t spend much time thinking about it, other than watching and observing and being entertained by it like we all are."

• The Pirates announced their minor-league coaching assignments for the 2023 season. The most notable changes are Callix Crabbe is moving from managing Class High-A Greensboro to Class AA Altoona, while Robby Hammock will manage Greensboro.

Kieran Mattison, who served as the Curve's manager last season, is staying wit hthe organization and will become the Pirates’ outfield, base running and Controlling the Run Game (CRG) coordinator in 2023.

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