When Waldman was on the Yankees beat for WFAN in the station's early days, Steinbrenner refused to talk to her; she was not invited to the annual lunch that the team held for beat writers at Manhattan's 21 Club. "Waldman sent an overnight letter to Steinbrenner at his office in Tampa," John Solomon wrote in
Sports Illustrated in 1997. "She pointed out that more people heard her daily reports on the highly rated Mike and the Mad Dog show than read the local sports pages, and she included a breakdown of the advertising rates the station received for her spots. 'I'm coming down to Tampa next Wednesday,
and I expect an interview,' the missive concluded."
Steinbrenner gave Waldman the interview, against what he considered to be his better judgment. "I like my women to spend my money and look real pretty," Waldman recalled Steinbrenner saying to her. "
I don't like them to be pilots, policemen or sports reporters." During her years covering the team, Waldman's relationship with Steinbrenner was as good as any relationship with Steinbrenner could be, which is to say that it whipsawed between sentimental largesse and wild roaring cruelty depending entirely upon the moods of one of the moodiest manchildren in sports history.
Steinbrenner bullied Waldman to tears, then receded to more acceptable levels of boorishness days later. In the peculiar ways in which Steinbrenner was loyal, though, he was loyal to Waldman, and if she was never quite safe from the blasting unmanned firehose of Steinbrenner's personal cruelty and sexism, he worked to protect her from the cruelty and sexism of others; when she received death threats from Yankee fans in 1989, Steinbrenner hired Waldman a plainclothes security detail. In 2012, Waldman told
Adweek that Steinbrenner was "
as important a human being in my life as anybody, except my family." The Yankees hired her as the color commentator for the team's WCBS radio broadcasts in 2005.