So these items are “kind of” cursed, where instead of them just being “using these are a bad idea” they are “using these are risky” these are potential gifts from the God of Chance, entertainment, gambling, and risk.

Any suggestions on these, or any new ones you think I should add?

Orb of random dragon! - Throwing this orb as a bonus action to the ground summons a draconic spirit from another dimension, roll to choose the color. It may or may not be hostile to you. The dragon can return to their plane at any time and vanishes back if slain. Single use.

Double or nothing - A magical coin with an X on one side and a winking dragon on the other. On taking damage, as a reaction flip a coin. Heads you take double damage, tails you take no damage. Single use.

Mirrored coin - On breaking this coin as a bonus action you let out an aura of bad luck that lasts for one minute. You have disadvantage on all saving throws, and any saving throws you force another creature to make they also have disadvantage. Single use.

Amulet of bloody good luck - Before making a saving throw you can activate this amulet as a reaction and roll a d10 and add the result to your saving throw. You take 5 force damage ignoring temp HP * the amount rolled on the d10.

Push your luck - On failing a saving throw as a reaction you may roll again using this bracelet, if you fail again you suffer the normal consequences as well as getting 2 levels of exhaustion.

Staff of odds - This magical staff with a laughing jester atop it has a -2 to hit on any spells cast from it, but crit on a 20 or 19

Call to the unknown - A golden wired diamond ear piece. Expend a spell slot as an action while targeting a creature. A spell of that level + 1 is randomly cast targeting that creature. Concentration is held by the Call to the Unknown and must be destroyed to end the effects early.

All on black - A necklace of a roulette wheel. As a bonus action activate the necklace by spinning it and roll a d10. On evens instantly have the benefits of a long rest. On odds, fall to 0 hp and become cursed for 12 hours. While cursed this way you are stable, can not regain HP, and this curse can not be removed except for Wish or act of god.

Dressed to kill - This wispy reaper like cloak means you no longer roll death saving throws, but die if you hit 0 hp as you are whisked into the cloak. Creatures you reduce to 0 hp instantly die even if they would normally stabilize or have death saving throws, as the soul is instantly brought into the shroud. The creature can not go to a clone or be revived until freed from the cloak.