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US prosecutors have gained an early edge in Raj Gupta’s insider trading trial. Judge largely adopted their version of a preliminary jury instruction a week after allowing them to introduce wiretap evidence. The former McKinsey & Co boss and director hasn’t put on his defence yet. But he’ll need some breaks soon if he’s going to beat the insider trading rap.

A difficult case for the government got a lot easier when Rakoff said last week he would probably permit jurors to hear recordings of jailed insider-trader bragging about confidential tips from a Goldman friend, allegedly Gupta. And after just two days of testimony, the mini-winning streak continued with the jury instruction. It was just a summary of the charges, something Rakoff typically provides to guide jurors as they hear evidence. But some defence attorneys argue that such summaries oversimplify cases, encouraging jurors to find guilt without proof of each element of a crime. And by adopting much of the prosecution’s suggested language in this case, Rakoff put Gupta in an early hole.

A big issue, for instance, is whether Gupta received any benefit from passing information to Rajaratnam, an essential requirement for an insider-trading conviction. The defence wanted “benefit” defined as “personal benefit,” believing the government can’t prove Gupta directly gained anything from speaking with Rajaratnam. But prosecutors pushed for “some kind of benefit, directly or indirectly, however modest,” hoping to make a conviction easier. Rakoff went with “at least some modest benefit,” basically the prosecution’s version.

That the two sides couldn’t even agree on the meaning of “benefit” highlights a more fundamental problem with the law against insider trading. Many situations, like the trading indiscretions of Berkshire Hathaway’s David Sokol, also turn on rubbery legal concepts with grey areas. Such a lack of clarity makes compliance with the law too difficult—and prosecutions under it too easy.

Gupta may yet turn things around. The case against him lacks the slam-dunk evidence that sank Rajaratnam, and his spotless reputation to this point should give his defence weight. But first impressions count, and thanks to Rakoff, jurors may already be growing sceptical.

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