Visual Description: Classic unlucky gambler, down to his last chips.
ROOLIE = ORIOLE, SOUTID = STUDIO, PHILSO = POLISH, WHYTOR = WORTHY, REESHA = HEARSE, GROUME = MORGUE — Giving us: RLSIOSOTYHRUE
Clue/Question: Wearing a tie to a fancy casino doesn’t mean you won’t do this.
Answer: LOSE YOUR SHIRT
HEARSE and MORGUE were two difficult (and downer) words to get. I had to resort to answering the Jumble first (pretty obvious, guys!), and then backing into the two words with the letters that I knew I needed. STUDIO, POLISH and WORTHY weren’t as automatic, for me, as ORIOLE was. All in all a pretty decent Jumble. I was kind of hoping for some kind of Mother’s Day tie-in though! — YUR
Unclerave's Wordy Weblog 
toughest Jumble I have seen in a while, that is for sure.