Trade deadline shenanigans

[Halejon/Nationals GM]

Ethics question: I have some players who are dead weight for the rest of this year but I would like to hang on to as they will reprice next year. I also have no picks left to trade until the end of the season. If I told an owner: 

"I know you don't really want player X but I will trade you player X for player Y on the (handshake) condition that at the end of the season you trade player X back to me for a Nth round pick, which is what you really want". 

Would people see that as sketchy? On the one hand, we've traded picks in advance with handshakes before. On the other, it kind of sidesteps cap limitations and other unspoken rules (like you can't trade someone for absolutely nothing even to cut cap because that goes against the spirit of trades). On the third hand, as long as the value was right I could probably accomplish something similar anyway, it would just be easier to figure out in advance how I get what I want back ahead of time with the same owner. 

Thoughts?

[Rockies GM (Mac)]

If you question it in your own mind, then it is sketchy. Go with your gut. It’s your conscience. Would you say to another person what was said to you?

[St. Louis Cardinals (Andrew)]

I don’t see an issue with it as long as you realise someone could go back on your agreement. We can’t have a binding agreement for future assets.

[Halejon/Nationals GM]

Aug 8, 2021 3:00:25 GMT -5 Rockies GM (Mac) said:

If you question it in your own mind, then it is sketchy. Go with your gut. It’s your conscience. Would you say to another person what was said to you?

While I think that's a good take on ethical dilemmas in general, what I think deep down isn't really what I'm looking for here. I personally have zero problem with it as I feel there's MLB precedent for this sort of thing (e.g. trading a guy for a PTBNL who ends up being that exact same guy). But based on previous discussions in this league I think there's a chance other people would differ and don't want to ruffle any feathers if that's the case.

[St. Louis Cardinals (Andrew)]

Each trade would have to pass the TRC though without any consideration for future trade.

[Halejon/Nationals GM]

Aug 8, 2021 4:57:41 GMT -5 St. Louis Cardinals (Andrew) said:

Each trade would have to pass the TRC though without any consideration for future trade.

Yeah, I agree. Thanks for the input. 

[Cincinnati Reds - Chris]

I'm also fine with it, along the lines of what Andrew posted.

[Deleted]

Zero ethical dilemma here for me either. Fair game.

[BrewCrewGM]

I’m sure this will surprise no one but I’ve already done this in years past.

[Deleted]

I have no issues with it, but would caution that the player would no longer be a free drop for you in the offseason if you traded him away and then reacquired him.