The Pittsburgh Pirates entered Thursday in an unenviable position. Not only are they anchored in last place in the National League Central — an afterthought in baseball’s tightest division through fourth place — but they’re 4-21 since the All-Star Game (edging the Tigers for baseball’s worst mark in that stretch) and have the worst record in the NL over their last 30 games. It’s not fun and games in Pittsburgh right now, basically.

You could argue this is a good thing, and an example of fortuitous timing. The Pirates are on the verge of an offseason in which they’ll need to make a number of important decisions. A prolonged stretch of putridness may strip the emotion from the equation and help the Pirates move in the right direction. We’re not making that argument, mind you, but we get it.

What kind of important decisions are we talking? Below you’ll find the four biggest questions the Pirates as an organization must answer ahead of the 2020 season.

1. Is it time to trade Vazquez?

We’ll start in an obvious spot: with Pittsburgh’s most sought-after trade asset. 

Felipe Vazquez is a nightmare on the mound. He throws in the upper-90s and has multiple swing-and-miss secondaries, including a slider that has coerced more than 33 percent whiffs this year. In addition to being one of the best relievers in baseball, lefty or otherwise, he’s signed to a team-friendly deal that will pay him just over $33 million over the next four seasons.

The argument for keeping Vazquez is that he’s too good and too cheap to move. The argument for trading Vazquez is that he’s a reliever and those break all the time. Think about how Edwin Diaz is viewed now and how he was viewed a season ago. Is Vazquez likely to fall off within the next year or two? No. But no individual elite reliever ever is, really. It still happens. Often.

Our guess is the Pirates will end up moving Vazquez this winter, perhaps even beating Cleveland to the punch on dealing Brad Hand. Teams value cost certainty and surplus value too much these days to let him toil in Pittsburgh. The Pirates should get a good return when they make a move, too — albeit probably not one led by Gavin Lux or a prospect of similar standing.

2. What about Marte and Polanco?

Have you looked at the Pirates’ payroll situation? If not, don’t worry — there isn’t much there. 

The Pirates have about a dozen arbitration cases to worry about for next season, and just four real commitments — and half of those are tied up in club options: Vazquez and fellow pitcher Chris Archer, and then outfielders Starling Marte and Gregory Polanco. As with Vazquez, it’s worth asking if the Pirates will move either Marte and/or Polanco ahead of next spring.

Marte seems likelier to go. He’s set to make more than $23 million over the next two seasons, and was already the subject of inquiries ahead of the trade deadline. Marte has been a reliable above-average contributor on all sides of the ball for years. Outside of a suspension-shortened 2017, he’s posted at least a 110 OPS+ in every season since 2013. Seeing as how he’ll turn 31 in October, it’s fair to wonder if he’ll slip any on defense or on the basepaths. Still, we’re talking about two more years — it’s reasonable to assume he’ll remain an above-average contributor through the 2021 season.

Polanco, comparatively, is a mystery man. He’s due $24 million over the next four seasons, and that’s with the buyouts exercised on two club options. Polanco enjoyed a breakout 2018, but has been limited to 42 games this season due to injury. You can blame his so-so performance this year on injuries, but he’s been roughly a league-average hitter over more than 2,600 career plate appearances. The Pirates will probably hold onto him, hoping that the 2018 Polanco was the new standard, rather than potentially selling low. There’s at least a chance that they’d be selling high — especially if someone shares their belief about 2018 being the new norm.

3. Should they exercise Archer’s option?

We’ve addressed three of the four Pirates with guaranteed money coming their way in 2020. Now, let’s talk about the fourth: right-handed starter Chris Archer. He has a $9 million option for next season that could be bought out instead for $1.75 million.

Regardless of what you thought about the deadline deal that landed Archer in Pittsburgh, it’s fair to write nobody saw this coming. In 20 starts this season, he’s posted an 82 ERA+ while running up would-be career-worst walk and home-run rates. On those grounds, rejecting the option seems like the sensible choice. 

Yet there is some reason to remain open to Archer turning things around. He can still miss bats — as his strikeout rate (10.2 per nine) indicates — and his average exit velocity is the lowest of his career (albeit still worse than the league-average). It’s hard to reconcile the latter with his home-run rate, but such is life when it comes to baseball analytics.

You can kinda, sorta see the makings of a rebound effort in there, right? Perhaps more so if you picture Archer wearing a different uniform … which brings us to our last question.

4. Is it time to change leadership?

Neal Huntington has been in charge of the Pirates since September 2007. That’s the fourth-longest tenure in baseball, behind only Brian Cashman, Jon Daniels, and Dayton Moore. Those three executives have each seen their teams win at least a pennant. Huntington, on the other hand, hasn’t so much as guided his team to the NLCS, or even a division crown.

Meanwhile, Clint Hurdle is set to become the longest-tenured skipper in the NL once Bruce Bochy retires this winter — by nearly four years. If Ned Yost walks away, too, Hurdle will have the longest managerial run in baseball. Again, he hasn’t won as much as a division title.

Now, look. It’s not fair to put the lack of banner-worthy material entirely on Huntington and Hurdle. They’ve fielded some very good teams that deserved more than they ended up with. But they’ve also made a number of mistakes — ranging from poor trades, to installing a culture that too often results in scraps with other teams, to retaining pitching coach Ray Searage despite there being ample evidence his philosophies no longer work as well as they once did.

Both Huntington and Hurdle are signed through the 2021 season. They’ll probably get one more season apiece. But jeez this franchise seems like it needs a new vision — and if this stretch of horrid play brings that about, then maybe it will come to be viewed as a plus.