From a lawyer's perspective, it's difficult to know if asking him to put on the glove at trial was the worst mistake in context that a lawyer has ever made, but it's certainly the most high profile. And knowing what I know now about being a lawyer, it was such a basic, arrogant mistake. When cross examining someone it is absolutely vital to know when to stop asking questions. So many inexperienced barristers and lawyers fall foul of this. When they get a good answer to a question, they get excited and ask an unnecessary follow up which kills the point ("Ah, so you did punch him first!" --> "No, no. It was after he shoved me"). I've been there, as every other trial lawyer has, but to see it done so flagrantly in such a high profile case is a horrendous mistake. There was no need to ask Simpson to put on that glove. There was loads of incontrovertible forensic evidence linking him to that murder scene. The case was won. And then, it was lost because of pure arrogance. We'll never know definitively if that's why he was acquitted of course, but given how famous the defense line became ("If the glove don't fit, you must acquit"), that's been one of the main conclusions. In any event, a completely avoidable error by the Prosecution.