Tsunade is a notorious gambler with terrible luck. In the series, she frequently runs from debt collectors, uses transformation jutsu to evade people she owes money to, and gambles away vast sums of cash.
To understand the meme, you have to break down its two cultural components.
: She repeatedly sent low-ranking Genin and Chunin, including Naruto Uzumaki and Shikamaru Nara, on high-stakes, borderline suicidal missions, such as the Sasuke Recovery Mission.