My Platinum (US, Delta) says $1k per occurrance, up to $50k per year, providing the purchase was charged to the card. I think you have to be the primary holder also (i.e. if you’re on your partner’s card, no luck). Also it’s secondary, so if covered by your house insurance for a part you have to claim there first. Lastly, it might only be theft and damage, not just losing it in the parking lot.

Some non-Delta cards might have a $10k limit, just searching briefly.

I just think with the exclusion list I was reading, you’re going to have a tough time with your $16k Rolex