Which 2023 2nd round pick is more valuable?

[Celtics2021]

The Celtics have two* second-round picks this year, one from Portland, and the other either from Houston, Dallas, or Miami.  Both picks seem to have a lot of variance as to where they end up:

The Houston-Miami-Dallas pick will come from Houston unless it's pick 31-32, in which case it's the lesser of Dallas or Miami.  In other words, this pick will either be in the high second-round (33-35) or in the 50s.  Currently the pick sits at 53, but Houston is a game away from sending us pick 33.  (Notably Houston doesn't control this pick regardless of its record -- if it's pick 31-32 it goes to Indiana).

Meanwhile, Portland is in the middle of the very jumbled group of teams near .500.  If the season ended today, it would be a reasonably valuable #43, but Portland is one game from having the 48th pick and one game from the 39th pick.

If you're a GM making a trade with the Celtics next month and are getting one of those picks, which would you ask for?  The one that is about 50/50 to be in the early 30s, but is otherwise in the 50s, or the one that will probably wind up in the 40-48 range?  I think the Houston pick is more valuable for the upside personally, but it's interesting conundrum (to me at least) for a Tuesday afternoon.

*The Celtics also technically have a pick from Orlando, but it reportedly only conveys if it falls between picks 56-60, which is a near certainty to not occur.  It's technically tradable, however.

[Vermont Green]

Great summary, thanks.  The conditions on these picks are confusing for sure.  That Orlando pick might be useful for a pure salary dump type of trade, something we might be willing to do with a TPE if we get back a useful vet at a position of need.  For the other two, I would trade which ever one the other team saw as having more value.  Neither is likely to get us a player that will even make the team.

We don't have a ton of 2nds for the next few years.  Haven't we traded away seconds in the following years:

2024
2025
2027
2028 (Protected)

2026 is a swap with Memphis so I guess still tradable.  Then we have conditional incoming seconds in:

2024 (Protected)

I guess you can buy second round picks but after this year, we may not see another second rounder until 2026.  I don't know what the protections are on the 2024 pick from SAN.

[footey]

Just read that Knicks willing to trade Cam Reddish for two second round picks. Not sure I would include the Houston pick, although I'd be pretty shocked if we get Houston's pick, since they are the most likely to lose for the Victor sweepstakes.  Most of the other teams aren't nearly as bad and dysfunctional as they are.

[Celtics2021]

Just read that Knicks willing to trade Cam Reddish for two second round picks. Not sure I would include the Houston pick, although I'd be pretty shocked if we get Houston's pick, since they are the most likely to lose for the Victor sweepstakes.  Most of the other teams aren't nearly as bad and dysfunctional as they are.

Detroit, Houston, and Charlotte are in a 3-way race for Victor, and remember that now the bottom three all get the same chance, so the incentive to finish dead last is slightly lessened.  The Rockets have yet to play either the Pistons or Hornets, but play both this month, so there could be some movement in the tanking standings.  The Spurs are hovering at 4th, and with the league’s worst point differential, they’ve shown they’re capable of losing to anyone they want also.

The Rockets and Hornets also play each other in game 81, so that could be a tanking game of epic proportions.