GREENBELT, Md. (AP) — Former Trump administration national security adviser John Bolton pleaded guilty on Friday to illegally retaining classified information, sealing a deal with federal prosecutors that could allow him to avoid a prison term. Bolton, who became an outspoken critic of President Donald Trump after serving in the Republican’s first administration, is scheduled to be sentenced on Oct. 28 by U.S. District Judge Theodore Chuang in Greenbelt, Maryland.Bolton pleaded guilty to a single count of illegally retaining classified information. His plea agreement with the Justice Department may enable him to avoid time behind bars, but the judge ultimately will decide his punishment.The plea agreement recommends capping any prison sentence at five years but the judge isn’t bound by that part of the deal. Bolton can withdraw his guilty plea if the judge issues a longer prison sentence or a fine greater than $2.25 million.

Bolton was charged last October with 18 counts of either retaining or disseminating classified information, including diary-like notes that he shared with relatives as he wrote a memoir about his career in government.

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Other Trump adversaries have been charged with federal crimes during his second term in the White House. While some of those cases have collapsed under judicial scrutiny and amid claims of political retribution, Bolton didn’t mount a vigorous defense against his charges before cutting a deal.