In conversations with POLITICO, current and former Bloomberg employees recalled the company’s struggles in 2016 as Bloomberg flirted with running for president, a situation made even more complicated by the company’s restrictions on covering Bloomberg the man and the organization.

Then, last year, Bloomberg mused in a Radio Iowa interview that he might sell his company or even cease political coverage if he decided to run for president in 2020. He initially declined to enter the race, before reportedly preparing to file papers for the Alabama primary, which has an early filing deadline.

“As long as he keeps doing this Hamlet-on-the-Hudson routine — he might get in, he might not get in — it really tortures the journalists working there,” Missouri journalism professor Kathy Kiely told POLITICO. “This is the time you want to be getting your feet under you, developing sources, setting up plans for coverage of the campaign.”

But Bloomberg "becomes an X factor and you don’t know what the landscape is going to look like for you and what you can cover," said Kiely, who believes the company's reporters should "cover Michael Bloomberg just like any other candidate."

Kiely, a former Bloomberg politics editor, quit that position in early 2016 out of frustration with not being able to aggressively cover Bloomberg’s political ambitions. She sees the newsroom constrained again heading into 2020.

“He’s hired terrific reporters, he has great editors, and then he goes and handcuffs them,” said Kiely, who suggests building a firewall between the potential candidate and the newsroom.

“Decide you want to be a publisher or a presidential candidate,” she added, “but you can’t do both and have a credible organization.”

As a matter of policy, Bloomberg News — which is part of financial and data juggernaut Bloomberg LP — does not cover Bloomberg’s “wealth or personal life” and “doesn’t originate stories about the company.” For instance, the company didn’t report on Bloomberg returning as CEO in 2014 after serving three four-year terms as mayor of New York City, news which broke in The New York Times.

Bloomberg News City Hall reporter Henry Goldman covered Bloomberg's time in office, but the newsroom did not deeply investigate the mayor and local city news has never been a major part of the global organization.

The race for the presidency, and the presidency itself, is a more consequential story for Bloomberg News, which employs many journalists focused on national politics and policy issues like taxes, health care, and the environment. It’s hard to see how cutting out “politics” wouldn’t impact a wide range of beats domestically and internationally, as well as the financial markets, which are a core Bloomberg News coverage area.

Bloomberg continues to serve subscribers of its high-priced terminals with up-to-the-second financial information, while also expanding its media footprint in recent years with magazines, like Bloomberg Businessweek, and through commentary and analysis at Bloomberg Opinion.

For now, journalists are reading Bloomberg’s comments in Iowa last year like tea leaves. In the radio interview, Bloomberg suggested putting the company in a blind trust or selling it. He reiterated that the company has “always had a policy that we don’t cover ourselves” and joked about how he didn’t want “reporters I’m paying to write a bad story about me.”

“One of the things you could do," if running, he said, "is you could say we’re not going to cover politics at all."

Nonetheless, Bloomberg's latest political move didn't go unmentioned on Bloomberg News.

Washington bureau chief Craig Gordon wrote a short piece Thursday evening on Bloomberg's political ambitions, though after news first broke in The New York Times.