Was winning bid your exact offer or did he offer more for signing bonus?

I will say one thing: having most - most, not all - of the Type As wait till one targeted cycle on the final day can absolutely leave you holding the bag.

Quite often (it's not a big secret, and you can't predict who I'm going after anyway) I'll go after my number 2 or 3 target instead of my number 1, and hope they sign fast. IMO it's an advantage just to have a player you wanted under contract early, it lets you set up any further moves you might be thinking of, and it locks out any other owner who might also be thinking of that guy as a fallback.

He was traded to your franchise the season before he walked. Loyalty bonus only applies if you had him for the full term of a five year deal AFAIK.

Also, for future reference, loyalty bonus guys will sign with their former franchise early in FA (assuming that franchise offered the max right off the bat). Him flipping back and forth was a tell that the loyalty bonus didn't apply in this situation.

Doesn't change the fact that it still sucks, sorry man

Most long time owner know the following:

The free agent period is 4 days long.
Day 1: No free agents sign
Day 2: 20-25% of free agents signings happen, spread randomly throughout this time window.
Day 3 - day 4 PM part 1 cycle: Another 20-25% of free agent signings happen, spread randomly throughout this time window.
Day 4 PM part 2 cycle: All remaining free agents with offers will sign.

I have seen Type A free agents sign on day 2 but I don't think I have ever seen a max contract signing on day 2. When offered a max contract, free agents usually (always?) wait until the Day 4 PM part 2 cycle to sign.

What I hate is that coaching signing is going on at the same time (mostly); which means you could lose the tie breaker because at the time of the FAs signing you didn't have a coach in that slot; but after all coaches sign you end up with the better coach.

There are a few things in Hoops Dynasty that are done really well that I feel like could be brought over to HBD if they ever decide to do an update.

Most notably in this case, recruits in Hoops (or free agents in HBD) have a signing preference. They will either prefer to sign early, late or whenever. If they put this as a preference for HBD free agents then you couldn't be upset if a guy signs on the last cycle. You can plan out a little better and not be left holding the bag. May change how free agents are targeted as well.

I can get waiting from the hypothetical FA perspective, but another reason it's a bit unfair to owners is because I've had owners that decide they're not gonna go after a big fish and just pursue their secondary options so they put offers out. They lose out on those options, so decide to put all their money back on a big fish, and a guy I've been leading on for 3 days, I suddenly have competition for. By having the big fish always wait until late to sign, it gives people a fallback if they miss out on other options, while the people who have had that player as their target the entire time potentially lose out.

That's why I said earlier: an early signing is a competitive advantage, which you acquire seemingly at random. There's invariably one Type A or very good B who signs immediately the first day. Trying to predict who that guy is is kind of my version of trying to generate a DiTR.