Former New York Deputy Mayor Howard Wolfson says, “Mike Bloomberg is not going to be intimidated by Donald Trump.”
Bloomberg “is not going to be afraid of Donald Trump. He has stood toe to toe with a lot tougher characters as mayor of New York, as a business leader,” Wolfson told David Axelrod on The Axe Files, a podcast from The University of Chicago Institute of Politics and CNN.
“You don’t get to be as successful as he has shying away from fights or being intimidated by people,” Wolfson added.
Wolfson, who worked briefly in journalism before turning to politics, said he realized he would rather “be the person in the room than covering the people.” Yet he believes his media background has given him valuable insight into the way politicians, especially President Trump, use the press to their advantage.
Trump “is a guy who mastered the New York City media environment,” Wolfson said. “And he understood that if you could be in the paper every day, controlling the story, or being part of a story, you were three-quarters of the way towards your goal. … I think he wakes up every day and instinctively understands that his goal for that day is to control that conversation.”
Wolfson said the President’s meeting on government funding last week with Senate Minority Leader Chuck Schumer and House Minority Leader Nancy Pelosi was an example of that strategy in action.
“He does have a pretty rich appreciation for what makes for good TV, why people tune in, why they stay. … If you combine the influence of the New York media market, the influence of successful television personality and the influence of a successful promoter, that’s Donald Trump.”
Both Schumer and Trump are New Yorkers, and Wolfson, a New Yorker himself, wishes this shared background between the two politicians would lead to more common ground when it comes to creating policy.
“The fact that you have two New Yorkers in such positions of power – but when you look at Trump’s positions vis-à-vis the city, they are negative here. Could you imagine a New Yorker … becomes President and signs legislation getting rid of the tax break that benefits New Yorkers?” Wolfson said.
Trump “is now single-handedly blocking funding for a really important tunnel between New Jersey and New York,” he said. “So I don’t know what it really means for him to be a New Yorker in the context of the things that New York needs.”
Today, Wolfson leads the education division of Bloomberg Philanthropies. However, he said, at one point he was “unkind” to then-Mayor Bloomberg. In 2003, he worked to defeat the nonpartisan election referendums that Bloomberg had put on the ballot. Despite this, Wolfson was hired onto Bloomberg’s team.
“This is a guy who looked at me and knew what I had said about him and was willing to take me on … trust me and put me to work. … There are some politicians who seem to want to make enemies and there are others who seem to want to make friends.”
Wolfson claims the Trump administration “has been a disaster in so many ways” and that Bloomberg has focused on problems the President hasn’t.
“So many of the issues that (Bloomberg) has spent a lifetime fighting for – whether it be gun safety, or the work on climate, or taking on the Big Tobacco consortia, or educational equity and opportunity, job creation – all of those things are under threat by this administration.”
Bloomberg, who was elected mayor as a Republican and an independent, re-registered as a Democrat in October and has been weighing a presidential run.
If Bloomberg were to run for president in 2020, Wolfson said, he would do anything he can to help.
“There’s a lot more you can do as president than you can as a philanthropist,” he said. “As great as his philanthropy is, if (Bloomberg) decides to run, it will be for that reason.”
CNN’s Devan Cole contributed to this report.