Several key allies of former President Donald Trump are facing daunting legal troubles, as law enforcement agencies continue the multiple investigations surrounding the inflammatory politician.

Allen Weisselberg, Trump's long-time chief financial officer, was sentenced to five months in jail by a New York judge, stemming from his role in a decade-long tax fraud scheme. Weisselberg previously testified as the state's witness against the Trump Organization.

Weisselberg, 75, is expected to be sent to New York's notorious Rikers Island jail. He pleaded guilty in August, admitting that from 2005 to 2017 he and other executives received bonuses and perks that saved the company and themselves money.

The former Trump Organization executive pleaded guilty to 15 counts of tax evasion and agreed to testify against the Trump Organization in return for the shortened sentence. Without a deal, Weisselberg faced a sentence as long as five to 15 years in prison.

The Trump Organization was found guilty of tax fraud in early December after a month-long trial. Weisselberg's testimony was central to the prosecution's case, which argued that the Trump Organization engaged in a 15-year scheme to provide its top executives with luxury perks to evade taxes.

Weisselberg has paid about $2 million in taxes, penalties, and interest as part of his punishment, and will likely serve 100 days in jail with time off for good behavior.

Many convicts in New York City facing one year or less behind bars head to Rikers Island, which lies between the New York City boroughs of Queens and the Bronx and houses more than 5,900 inmates. Nineteen inmates died there last year, as the facility is well known for violence, drugs, and corruption.

In another twist for a prominent Trump ally, former New York City Mayor and Trump attorney Rudy Giuliani has been subpoenaed by the Department of Justice, asking him to turn over records to a federal grand jury as part of an investigation into the former president's fundraising following the 2020 election.

The subpoena was sent in November and first reported by CNN, and seeks documents from Giuliani about payments he received during the period when he was filing post-election lawsuits on behalf of the Trump campaign.

Prosecutors specifically asked for documents related to disbursements from the Save America PAC, Trump's primary fundraising operation set up shortly after the 2020 election, reports CNN.

Giuliani has not been brought up on any charges, and prosecutors have issued subpoenas for other close Trump allies.

Giuliani was responsible for peddling several false claims following the 2020 presidential election, as he led the campaign's litigation response following Trump's loss, including that Dominion voting machines across the country were hacked.

Giuliani, like Trump, was among those whom the House Jan. 6 panel recommended the Justice Department evaluate for possible criminal charges.

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