Asisreo
Patron Badass
I agree with the bad luck and the monster being particularly harsh but I do believe the players were at least doing the best choices with what they knew on-hand.Anyway... this sounds like a combination of an extra-nasty monster, bad luck, and poor tactics. The party was failing to coordinate at all and the spellcasters were making poor choices--which isn't uncommon, I see both things fairly often, but in this case the monster's abilities were absolutely unforgiving of those errors. (The wizard's gambles with hypnotic pattern were bad bets against a "caster monster," but could at least have paid off big, and the wizard had no way to know the flayer was magic resistant. The cleric made the worst mistakes, first by not moving next to the monster so the rogue could Sneak Attack, and second by casting bless in the clutch moment instead of something that could have damaged the flayer and/or extricated the paladin.)
They aren't metagamers and don't know the features, HP, traits, etc. when being introduced to a new monster until I display them. They probably even thought that it was a boss battle when they saw the flayer with a recharge ability. They didn't know how close he was to death but they did know that the fireball that the wizard threw didn't bring him down to being "bloodied." They knew they needed at least 2 more fireball-worthy attacks.
The cleric didn't want to be caught into whatever tentacle thing I put the Paladin in, because the Flayer absolutely can tentacle multiple creatures at once. He didn't know this, but the cleric is the only one with resurrection-type magic so he didn't want to risk it. He did try Spiritual Weapon and hit with that but its not enough damage to have saved the paladin even with Spirit Guardians. He was close to the Paladin for the save buff but he didn't want to be targeted immediately. He also wants to keep a 3rd-level slot handy for revivify.
Wizard really didn't have alot of options. Of the 12 spells he had access to, 2 of them were 4th-level spells which he didn't have due to the previous fight. 4 of the 3rd-level spells were counterspell, dispel magic, Fireball, and Hypnotic Pattern. His 2nd-level spells are Misty Step, Invisibility, and Rope Trick. His 1st-level spells are Mage Armor, Shield, and Magic Missile.
His options were basically do damage or Hypnotic Pattern to immediately stop everything.
I think I might be a lucky (unlucky) DM since my players say I get high numbers too often. Their saves were also tragically bad, though I kinda expected the Paladin to be stunned when I first prepped the encounter.