The use of large language models either as decision support systems, or in agentic workflows, is rapidly transforming the digital ecosystem. However, the understanding of LLM decision-making under uncertainty remains limited. We study LLM risky choices along two dimensions: (1) prospect representation (based on an explicit representation or outcome history) and (2) decision rationale (explanation). Our study, which involves 20 frontier and open LLMs, is complemented by a matched human subjects experiment, which provides one reference point, while an expected payoff maximizing rational agent model provides another. We find that LLMs cluster into two categories: reasoning models (RMs) and conversational models (CMs). RMs tend towards rational behavior, are insensitive to the order of prospects, gain/loss framing, and explanations, and behave similarly whether prospects are explicit or presented via a history of outcomes. CMs are significantly less rational, slightly more human-like, sensitive to prospect ordering, framing, and explanation, and exhibit a large description-history gap. Paired comparisons of open LLMs suggest that a key factor differentiating RMs and CMs is training for mathematical reasoning.