To trade a guy or not to trade a guy?

Neither seems a terribly appealing plan for the White Sox right now.

Rick Hahn’s job is making these kinds of tough decisions, so something’s got to give in an offseason that has really yet to get going, in terms of completed transactions, for a team that has a lot of improvements to make after finishing .500 and missing the playoffs last year.

But any discussion about those kinds of decisions – usually as nothing more than speculation – reveals that this is no enviable position to be in.

Liam Hendriks is just about the only name of a White Sox player that’s come up since the Hot Stove season started, mentioned during the Winter Meetings as someone the team is “listening” to offers on. Hahn’s response to those rumors was spot on: The White Sox’ front office listens, literally, to just about everything. That’s called those guys doing their jobs.

But it brought up the notion of the team potentially parting with its All-Star closer to fill holes elsewhere. And I think that seems a little ridiculous. Hendriks has been arguably baseball’s best ninth-inning man over the past four seasons, and though he’ll be the first to tell you he wishes he’d done better in 2022, he was still a terrific closer, the White Sox getting their money’s worth after inking him to that big free-agent deal ahead of the 2021 season.

While bullpen arms, in general, might not be too difficult to find, and while the White Sox have spent somewhat heavily to deepen their bullpen in recent years, creating a closer problem is not at all what a team trying to win the World Series wants to do. Is the South Side bullpen a strength? Absolutely. Should any team looking to get better try to trade from a position of strength? Absolutely. But what assurances are there that Kendall Graveman or Reynaldo López or Joe Kelly or Garrett Crochet would be able to master the ninth inning the way Hendriks has? None.

But Hendriks is, of course, just one player on the roster, and when you’ve got five podcasts a week during a .500 season, you get around to discussing the viability of trading just about all of them.

We’ve done it. And the same problem pops up again and again.

If Hahn deals a star like Hendriks, he could get back the kind of player or players that would plug the White Sox’ holes at second base or in left field, not to mention the less position-specific needs the team has, such as left-handed hitting, power, speed and defense. But doing so creates another hole in the process.

It’s like a cartoon character trying to plug the rapidly appearing holes in a sinking rowboat. Dealing someone like Hendriks might plug one hole, only for another hole to pop up. And the White Sox might not have enough cartoon limbs to plug ‘em all.

It’s why their advertised unlikelihood to spend significantly more in free agency is so confusing. Forget all of your complaints about how a large-market team should be acting. It’s more about how a team in the very specific situation the White Sox are in could act to get themselves out of it.

Because while trading someone like Hendriks – or Tim Anderson or Eloy Jiménez or Luis Robert – seems ridiculous, the White Sox have made it clear that they expect their chief way of acquiring external pieces this winter is via trade. Those high-profile players are perhaps the only way the White Sox can get major league talent back. And yet, they seem like the kinds of players usually dealt away by rebuilding teams for a big prospect haul, not traded away by a team trying to win it all.

The White Sox shouldn’t be trading players like that in the middle of a supposed contention window, they should be trading for them. But they might not have the prospect depth to do it. Hahn & Co. don’t seem to want to part with Colson Montgomery or Oscar Colás, the latter perhaps penciled in for an everyday job at the big league level in 2023, but who else is there to make an attractive enough package to land an impact major leaguer? Bueller?

And round and round we go.

You might volunteer players coming off down years, like Yoán Moncada, Yasmani Grandal and Lucas Giolito, as potential trade-away options. But those players come with bottomed-out trade value and veteran salaries, making things difficult. Shout out Gavin Sheets and Leury García’s names all you want, those guys are the ones the White Sox are trying to find upgrades over.

So who knows what it will look like when the White Sox do pull off a deal, and considering the holes that need filling, there will be a deal or two before Opening Day. There has to be. Get your “I can’t believe they’re done after signing Mike Clevinger” takes out of here.

But will it be one that creates a new hole on the big league roster? One that strips away the organization’s best minor league talent? Or one that fails to return something good enough to make the improvements this team needs to contend for a championship in 2023?

As you can see, it’s not so easy to play “Let’s Make A Deal,” not in the situation the White Sox are in.