How Can the Pittsburgh Pirates Win, and How Long Could It Take?

It's difficult to determine how Pittsburgh Pirates' GM, Ben Cherington wants to build this team. Let's take a look at some options.

The longer your team goes without improving or altering the roster, the wilder the speculation becomes. We’ve written on this very site about scenarios like What if Bob Nutting Spent, Should the Pirates Rebuild, Free Agent Targets, and so on and so on. I regularly get asked by readers how can the Pirates get to the point where they can win a division and when. In fact, one of our more active commenters specifically wanted to see how I felt about 2021 being a target.

These questions got me thinking, the Pirates haven’t moved anyone of significance as of yet so let’s look at some different ways I see as a path forward for the Pirates to actually win the division, and ideally more. Keep in mind, these will all be what I personally would do, not based on insider information or the rumor mill, simply how I think they could actually make this happen.

I’ll also not be asking Bob Nutting to spend one dime more than he has in the past. My reasoning for this has nothing to do with thinking how he spends is adequate, but I’m quite literally sticking with what I deem the reality.

Everyone loves playing GM, especially me since those are my initials.

2021 (Payroll Budget near $75 Million)

Things that need to happen:

1. Can’t trade Marte, Bell or Frazier
2. Taillon must return healthy
3. Keller must take a step forward
4. One of these need to debut and be an answer; Jared Oliva, Mason Martin, Oneil Cruz

Why I think this is possible: 

1. The talent at the AA level is truly intriguing, and I believe at least two of these players will be contributors by 2021
2. An outfield with Marte, Reynolds, Polanco, Cruz, Oliva, Martin as options would be outstanding
3. An infield with Hayes, Newman, Frazier, Tucker, Bell, and Moran would be defensively sound even if Bell doesn’t improve
4. The payroll doesn’t really increase much beyond arbitration numbers

Variations 

1. Trade Marte and trust the talent coming plus whatever is returned
2. Sign Bell to extension, even if slightly overpaid (payroll up to $85 million)
3. Extend Joe Musgrove to add another layer to firm up rotation (payroll up to $92 million)

Dangers

1. Run the risk of getting nothing for Marte
2. Taillon is no guarantee to return healthy or stay that way
3. Bell may not be open to extension, but not trying would be a mistake. To make a run you could excuse getting nothing for Marte, but not both

2022-2024 (Payroll Budget near $85 Million)

Things that need to happen: 

1. Must trade Marte (present day), and just get best available package
2. Quinn Priester must ascend through the system
3. Keller must take a step forward
4. Trade Polanco in 2021
5. Either Bell has been extended or this could be his last season

Variations 

1. Move on from Bell, but Craig has to work, or Moran needs to move to first
2. Sign Bell to extension, by now he costs more I believe (payroll up to $100 million)
3. Add a rental pitcher at the deadline (payroll up $105 million pro-rated)

Dangers 

1. Run the risk of getting nothing for Bell
2. This asks Nutting to stretch the payroll to the top of what we’ve seen him do.

2023-2025 (Payroll Budget near $65-75 Million) Full Rebuild Option

Things that need to happen: 

1. Must trade Marte (present day), and just get best available package
2. Trade Frazier, Moran, Polanco, Archer and Bell. Possibly Williams, as well
3. Can’t rule out moving Taillon in 2021
4. Need to return some pieces that contribute for this window, especially pitching and catching

Why I think this is possible: 

1. If the Pirates choose to full rebuild, this is the realistic window that opens
2. The club can only get stronger through good baseball moves to bring in young talent
3. Young pitching is from an internal standpoint 100% on Keller and Priester, important to get someone in return 

Variations

1. Any of the proposed trade pieces could be extended to cover this window if they are viewed as valuable to the cause
2. Reynolds will need to be included in the discussion for an extension as his time will come during this window.
3. If Bell is the “face” his extension could increase payroll by $20 million AAV
4. Timing is important, this date range works because you can comfortably trade for lower level, higher upside prospects

Dangers 

1. Every rebuild is based on faith, if you don’t trust your scouts you have no business trying to attempt this process
2. This will not be popular. That may not matter but it is a reality.
3. Young players fail to reach potential all the time in MLB, important to get more than one possibility at most positions, especially pitcher

These are the three windows I can see being realistic to target and the ways to achieve them. So why not add 2020? Because I don’t see it as realistic. I never did, but now that the majority of impact players have been inked to new deals it is not only unrealistic it is confirmed not possible. The Pirates need to have at least two top tier starting pitchers and I don’t see that being possible until 2021.

If the Pirates were to go with the 2021 option, I believe it is a one-and-done window. It's high risk, high reward. The team could really be solid, but the offseason following 2021 would be painful. A successful small to mid-market club tends to lean toward the 2 to 3-year window model as it provides wiggle room to hit the right mix. Additionally, that’s a lot of pressure to put on a guy returning from his second TJ surgery.

The 2022 to 2024 window allows you to keep much of what you like on the roster currently and gives Taillon another year to fully recover/reacclimate. It also gives time for a third option in Pirester. If they choose this option, the payroll will go up, but they need to fill any holes from the outside, and it’s not been the way they’ve done business. While I give Ben Cherington a chance to be different, I really must see it to believe it. Again, trying to stay realistic.

Finally, the third window 2023 to 2025 is the full rebuild option. This largely makes the team you see today unrecognizable but has potentially the highest upside. The club has some nice pieces in AA and below, this would allow them ample time to develop and integrate prospects returned in deals, so they grow together. It’s a new core and Reynolds/Newman/Keller/Priester need to be the centerpieces. Still a whole lot of unknowns here, I mean how could we possibly know what to expect in return for trades we haven’t even seen rumored yet? But if this is the way they go, they don’t really have to start until the trade deadline this season or the offseason after 2020.

Obviously, there are variations for all of these you could propose, perhaps you think Keller is never going to be that good, I can’t argue but I can say his name could be swapped with a prospect returned. Maybe you’re a sign Marte for five more seasons person, I find it unlikely but who knows, that could really change things. Maybe Chad Kuhl comes in this year and absolutely shoves and becomes part of the answer. 

One thing you don’t see in any of my proposals is the Pirates continuing to float around the wild card borderline. I think if the team remained healthy last season that’s exactly where they would have fallen and that simply can’t continue to be good enough. The formula is pretty simple, identify a date range to win, identify who will be part of that core, take steps to surround that core to cover that window.

Now that we have a GM who has done this very thing in his previous employment, let’s see what he comes up with. Here’s hoping half measures are not in his recipe book for cooking up a winner.