[Serious] Solicitors/Lawyers; Whats the worst case of ‘You should have mentioned this sooner’ you’ve experienced?

Hoping ya get some answers OP

Had a client arrested for auto theft twice in a two-week period. He had quite the convincing story, whereby he had a rental agreement with the owner of the car and through a misunderstanding, he missed a payment and the owner overreacted and called the police. We spent a good deal of time discussing this, he had supporting documentation, it was an easy win. This was clearly a civil matter, not a criminal one, as the owner had willingly given him access to the car in exchange for a payment plan that went bad.

I met with the prosecutor for the first time and, as customary, he asks for my take on things (this was before any discovery is ever exchanged). I explain the misunderstanding. The prosecutor looks at me and says “okay, but what about the other car?”

…whole time my client insisted he was arrested for the same car both times. He wasn’t. He was in a different “totally not stolen” car each time.

We’re rooting for you, OP!