In an upcoming draft I have 2 compensation A picks and 3 compensation B picks.
(My original 1st round pick went to another team for signing a FA.)

If, for example, those first 5 picks don't sign (after I give an offer) - how many compensation picks would I receive for next season's draft?

You don't get comp picks for unsigned comp picks. You have to use those comp picks this season.

The above is correct. The only thing I would add that confused me when I first started was that if you have a type A pick, you receive two pieces of compensation.
1. You receive the actual pick (typically the 1st or 2nd round, with a few exceptions) -- this pick does qualify for type D compensation.
2. You receive the supplemental pick (a pick between the first and second round). -- this pick is not eligible for the type D.

So any type B supplemental pick that you draft and do not sign will not get you a type D the following year. Any type A supplemental pick will also not net you a type D. Type D is only awarded for actual picks, not supplemental picks. To answer your question directly, if all five guys refuse to sign (highly unlikely), then your maximum number of type D picks, is two -- the two actual picks t(non-supplmental picks) you received from the type A comp picks.

If you go to GM/player development/amateur draft order, any pick with a * next to it is not eligible for type D compensation.

The actual Type A qualifies for compensation next year? Not sure if I remembered that or not. My apologies.

Posted by damag on 10/14/2019 12:15:00 PM (view original):
The actual Type A qualifies for compensation next year? Not sure if I remembered that or not. My apologies.

I just learned this only a few months back. I was surprised by it, but it is true.

Thanks for the answers.

tlowster - going by the * rule - only one of my Type A picks is eligible - but FYI - it was one player.

Posted by dschang on 10/15/2019 1:35:00 AM (view original):
Thanks for the answers.

tlowster - going by the * rule - only one of my Type A picks is eligible - but FYI - it was one player.

Your team might have received a lower comp pick. Sometimes the same owner will sign multiple type A free agents and your comp pick dips below the second round. If that is the case, then only one of the five picks will be eligible. Easiest way to check if this is the case is to see if you have more than one pick in one of the rounds past round 2.

Posted by tlowster on 10/15/2019 6:34:00 AM (view original):

Posted by dschang on 10/15/2019 1:35:00 AM (view original):
Thanks for the answers.

tlowster - going by the * rule - only one of my Type A picks is eligible - but FYI - it was one player.

Your team might have received a lower comp pick. Sometimes the same owner will sign multiple type A free agents and your comp pick dips below the second round. If that is the case, then only one of the five picks will be eligible. Easiest way to check if this is the case is to see if you have more than one pick in one of the rounds past round 2.

I had a Type A signed recently and received a 5th rounder in compensation because that owner had signed so many Type A's. It sucked.

Posted by Jtpsops on 10/15/2019 11:51:00 AM (view original):

Posted by tlowster on 10/15/2019 6:34:00 AM (view original):

Posted by dschang on 10/15/2019 1:35:00 AM (view original):
Thanks for the answers.

tlowster - going by the * rule - only one of my Type A picks is eligible - but FYI - it was one player.

Your team might have received a lower comp pick. Sometimes the same owner will sign multiple type A free agents and your comp pick dips below the second round. If that is the case, then only one of the five picks will be eligible. Easiest way to check if this is the case is to see if you have more than one pick in one of the rounds past round 2.

I had a Type A signed recently and received a 5th rounder in compensation because that owner had signed so many Type A's. It sucked.

Yeah. I hate that. Just another way the consistently successful teams get punished -- the teams with the better record get pushed down the draft board on comp picks.

Related followup question regarding a different draft.
1st pick.
Offer contract - player is considering a college, etc.
Player wants to play baseball but increases his demand (by a lot actually).
At this point, if you do not offer/sign the player - do you still receive a compensation pick based on initial offer?
If you offer a lower amount and player declines (I did this actually) - do you still receive a compensation pick based on initial offer?

Hopefully someone can clear this up for me.
I dunno if this guy is worth 8M signing bonus.

Do not offer him anything after the initial offer. Once he come's back with a higher demand, let it be and you get the comp pick the following year. I did this with the same comp pick 2 drafts in a row starting with the #1 pick as the team I took over had low scouting budgets. This season at #3 overall I finally got my ace SP!

hmm i made another offer which he rejected.
does this qualify?

Posted by dschang on 10/17/2019 8:35:00 PM (view original):
hmm i made another offer which he rejected.
does this qualify?

If you offered him 100 percent of his current demand, then yes.

no - it was less than the higher demand he came back with. was just curious if he would accept a lesser amount at that point.
i'm just going to leave it be - I can't imagine many first round draft picks being worth 8M.