I was retiring some oldies and came across this guy - Windy Flag
I brought him via a FF auction mid 2021, he’d won 2 Stakes races and looked a stallion prospect, I paid $900k 
Safe to say he didn’t repay that, unable to win another race, I tried all distances, gear, tracks and his jumps trials were terrible.
He’d have to be my worst purchase ever!
I apparently bought Faith Hill from FF at auction for just over $5 mil. She had 4 foals after that, for whatever reason I sold all of them (grand total 200k across all 4). At least they earned me ~1mil pre-sale? 
Not sure if she’s my worst, but she’s the most expensive, at any rate.
Ohh I think I have a few, but most memorable is Suvin IV. I was convinced he was going to be a MSW and possible stud candidate. Yeah that didn’t happen in the slightest. Paid $100k+ and he only won $36k at the track.
I’m sure there are more lol
Now that he’s retired I looked up his stats. They’re…not great. 
His stamina was less than 5f, so I have no idea how he won those 2 stakes at 10-12f. Also zero courage, zero consistency, hated everything (not just jumps). Also he was over the hill once he hit 5, so I bet he hated his life for the last 4 years racing. 
That information would be so nice to see while playing
It really would!
Too many flops to mention in my stable 
Sorry, in this case I meant Windy Flag. Not sure why it didn’t link my post to @Andy 's original.
Suvin’s stats are actually decent. Of the two, I would have picked him as a MSW over WF.
Sunday Joy was purchased for just over $600k. She won just over $100k and only foaled a single stakes winner.
Well at least I wasn’t too crazy in thinking he had potential 