Limbaugh claimed Jennings “encouraged” relationship between student, adult

Limbaugh: “Obama's safe school czar is a guy promoting homosexuality in the schools and encouraged a 15-year-old kid to have a homosexual relationship with an older man, and even facilitated it.” During the September 28 edition of his radio show, Limbaugh sought to compare film director Roman Polanski, currently facing extradition for the 1978 rape of a 13-year old girl, and stated, "[I]f you wonder why the libs are really ticked off that Roman Polanski might be extradited to face the music on that long-ago act with the 13-year-old girl, Quaaludes and rape, understand that Obama's safe school czar is a guy promoting homosexuality in the schools and encouraged a 15-year-old kid to have a homosexual relationship with an older man, and even facilitated it." [Premiere Radio Networks' The Rush Limbaugh Show, 9/28/09]

Evidence does not support claim that Jennings “encouraged” and “facilitated” relationship

Jennings: “I listened, sympathized, and offered advice.” In his 1994 book, Jennings described “Brewster” as “a charming but troubled kid” who “was not very happy with himself.” Jennings wrote that he “didn't have a clue as to why -- at least not at first,” and went on to describe an incident in which “Brewster” was brought into his office and discussed his homosexuality by telling “a story about his involvement with an older man he had met in Boston.” Jennings wrote that he “listened, sympathized, and offered advice,” and “Brewster” left his “office with a smile on his face that Jennings ”would see every time" he “saw him on the campus for the next two years, until he graduated.” From his book:

I remember Brewster, a sophomore boy who I came to know in 1987, my first year of teaching at Concord Academy, in Concord, Massachusetts. Brewster was a charming but troubled kid. His grades didn't match up with his potential, his attendance could be irregular, and he often seemed a little out of it. He was clearly using some substance regularly, and was not very happy with himself. But I didn't have a clue as to why -- at least not at first.

[...]

Toward the end of my first year, during the spring of 1988, Brewster appeared in my office in the tow of one of my advisees, a wonderful young woman to whom I had been “out” for a long time. “Brewster has something he needs to talk with you about,” she intoned ominously. Brewster squirmed at the prospect of telling, and we sat silently for a short while. On a hunch, I suddenly asked, “What's his name?” Brewster's eyes widened briefly, and then out spilled a story about his involvement with an older man he had met in Boston. I listened, sympathized, and offered advice. He left my office with a smile on his face that I would see every time I saw him on the campus for the next two years, until he graduated.

I was thrilled to be able do for Brewster what I had wanted Mr. Korn to do for me ten years before. But the conversation also left me troubled. I had been playing a variation on the “don't ask, don't tell” game with my students. If they asked, I told, but otherwise my sexual identity was not a fit topic for discussion. I grew uncomfortable with the message this was sending, with the air of secrecy and shame and scandal that my quasi silence implied. I decided I needed to come out in a more forthright and honest fashion, and made plans to do so the fall of 1988, my second year at Concord. [One Teacher in Ten, pages 24-25]

Jennings later said he counseled on the use of condoms to prevent HIV. In a 2000 speech to the Gay, Lesbian and Straight Education Network (GLSEN), Jennings offered more detail as to the advice he gave to “Brewster.” Jennings said after “Brewster” told him of the incident involving an older man, “I didn't know what to say, knew I should say something quickly. So I finally -- my best friend had just died of AIDS the week before -- I looked at Brewster and said, 'You know, I hope you knew to use a condom.' He said to me something I will never forget, He said 'Why should I, my life isn't worth saving anyway.' ”