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Three thoughts on Pirates' offseason

December 3, 2020

PITTSBURGH -- The first week of December is nearly over, the non-tender deadline is in the rear-view mirror, and there’s snow on the ground outside my house. This is typically the time to start thinking warmer thoughts -- San Diego, Las Vegas, even Disney World -- and pack a suitcase

PITTSBURGH -- The first week of December is nearly over, the non-tender deadline is in the rear-view mirror, and there’s snow on the ground outside my house. This is typically the time to start thinking warmer thoughts -- San Diego, Las Vegas, even Disney World -- and pack a suitcase for the Winter Meetings.

But since this is 2020, it’ll be a virtual version of baseball’s annual meetings that takes place next week -- and it won’t be the same. There’s nothing like having the entire industry inside a single hotel, randomly running into someone who enlightens you on some bit of news or refreshing your Twitter feed in abject panic after seeing MLB Network insider Ken Rosenthal zip across the lobby while on the phone.

More than anything, I’ll miss the rare opportunity to catch up in person with my colleagues and friends from around the country, all in one place. But with that off the table, hopefully next week will at least deliver a little more Hot Stove activity than we’ve seen so far this offseason.

While we wait, here are three things I’m thinking about the Pirates.

1. What’s the timeline?

We’ll start with a thought inspired by an interesting email from reader Chad R. on the most important big-picture question facing Pittsburgh’s baseball operations department: “If it took former general manager Neal Huntington until season No. 6 to turn the Pittsburgh Pirates into a playoff team, how long do you think it will take current Pirates GM Ben Cherington? I'm going to say it will take 4-5 seasons, but maybe it's because I'm optimistic.”

They can certainly be even more optimistic that everything will break their way and they’ll sneak into a potential expanded postseason in the next year or two, but I think Chad’s about right with that timeframe of 4-5 years.

When we talk about stuff like this, it’s important to remember that everyone on the team must believe they have a chance to win every game they play. It’s just the way they have to be wired as athletes and competitors: You show up every day to win. So, I wouldn’t expect anyone in the organization to come out and say they’re years away from contending. That’s not fair to the people in the clubhouse, even if they understand the business of baseball.

But it’s clear the Pirates’ focus is on the future, and their language for the last year has been centered on the idea that they are building toward something. Team president Travis Williams touched on that “trajectory” -- and their emphasis on continuing to acquire and develop prospects -- when we spoke last week.

I think I mentioned this last offseason, but it seems realistic that their window could legitimately open again around 2023.

At that point, core players Ke’Bryan Hayes, Mitch Keller, Bryan Reynolds and Kevin Newman should still be around as established big leaguers. First-round pick Nick Gonzales should be manning second base, perhaps alongside shortstop prospect Liover Peguero or Ji-Hwan Bae. Travis Swaggerty could join Reynolds in the outfield, and maybe Oneil Cruz will move to right field and succeed Gregory Polanco. Young first baseman Mason Martin might be bashing balls into the Allegheny River.

Within the next three seasons, it’s possible you’ll start to see pitchers Quinn Priester, Brennan Malone, Tahnaj Thomas, Braxton Ashcraft, Carmen Mlodzinski and Max Kranick join Keller, Blake Cederlind and others in Pittsburgh. And this time next year, we could very well be talking about whoever the No. 1 Draft pick is next year -- Kumar Rocker? Jack Leiter? High school shortstop Jordan Lawlar? -- as a central figure in the next wave.

That’s a pretty good starting point, and it’s worth noting that the Pirates don’t have anybody on a guaranteed contract for 2022 or ’23. A chunk of their current core -- Josh Bell, Jameson Taillon, Adam Frazier, Joe Musgrove and Chad Kuhl -- will reach free agency after 2022. So there’s going to be payroll flexibility – the critical question of how much, obviously, depends on ownership -- and a couple years for Cherington to figure out how to best use it.

Now, as harsh as this may sound: Not all of those prospects I mentioned will pan out. It’s easy and unfortunately common for us to look at young players and project that they will all reach their absolute 100th percentile outcomes, creating unfair and unreasonable expectations. Teams need depth in the Majors and on the farm, and building that kind of depth takes time.

But that core group of young players, combined with the talent Cherington is working to acquire now and the proven players he’ll be able to add if given the necessary financial backing, should help make the Pirates competitive a few years down the road.

2. Speaking of the future…

I think one difficult aspect of following a rebuilding team -- or whatever you want to call it -- is that it can all feel so abstract. You’re monitoring Minor League box scores, poring over prospect rankings, reading scouting reports and trying to project performance at the highest level while your most direct relationship to baseball is still typically with the big league team playing on your TV (or on MLB.TV) every day from March through September.

Watching a winning team is fun. Talking about a team that’s going all-out to win is fun. But it’s a little harder to be romantic about baseball when you hear the Orioles’ Mike Elias say his team is not yet set on “maximizing wins in the upcoming season” and that this stage of Baltimore’s rebuild “isn’t fun.”

Short of trying to sell people on the idea of General Manager Fantasy Camp, I think the best way for teams to encourage fans to invest in this part of the process is to be honest about where they are and what they’re doing, put some personality behind it and try to make it more fun. Ultimately performance is what matters most, but it’s still easier to root for people than it is to pull for farm system rankings.

So, kudos to the Pirates for starting some prospect-focused accounts on Twitter and Instagram – both @YoungBucsPIT – and trying to shine some light on where their baseball operations department’s focus will be. Their crew spent time at the instructional league camp in Bradenton, Fla., and it sounds like they’re planning to roll out player features, interviews and other stuff to help fans get to know the prospects -- as players and as people -- while following their progress through the system.

3. Rule 5 ready

After non-tendering Clay Holmes on Wednesday night, the Pirates have an open spot on their 40-man roster. As long as that remains true for the next week, they’ll be able to make a selection with the first pick in the Rule 5 Draft.

Even with all the challenges associated with this particular Rule 5 Draft -- no Minor League season, limited scouting opportunities, etc. -- it seems highly likely the Pirates will choose someone atop the Draft. It’s a very low-risk, potentially high-upside move, and they have plenty of time to let it play out.

Five names that stand out to me, compiled from MLB Pipeline’s list of the top eligible prospects from each team:

• INF Kevin Smith, Blue Jays No. 19 prospect: Defensive versatility at three infield spots helps, as does his history with Cherington and assistant GM Steve Sanders. They saw him hit really well -- a .302/.358/.528 slash line with 25 homers, 93 RBIs and 29 steals -- during his first professional season in 2018.

• RHP Garrett Whitlock, Yankees: A potential multi-inning arm with Double-A experience? Even after Tommy John surgery, Whitlock seems like someone the Bucs could find room for in the bullpen.

• RHP Jose Alberto Rivera, Astros No. 14 prospect: Another potential multi-inning arm, this time with a fastball that tops out at 100 mph. I’ll emphasize multi-inning arms a lot this offseason, in part because of the uncertainty regarding how many innings Pittsburgh's starters will be able to handle after such a weird workload this year. Also, it’s typically easier to stash Rule 5 picks in the bullpen than anywhere else.

• RHP Alex Speas, Rangers: This would be a real upside play, given how little professional experience he has, but he was a highly touted prospect in the Draft with a triple-digit fastball and huge strikeout numbers in the low Minors.

• C Julio E. Rodriguez, Cardinals No. 15 prospect: You may have heard that the Pirates could use some prospects behind the plate. Maybe they’re better off next season with Jacob Stallings and Michael Perez, but why not take a shot on a good defensive player with upper-level experience out of a traditionally productive farm system?

Adam Berry covers the Rays for and covered the Pirates from 2015-21. Follow him on Twitter @adamdberry.