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Saying Jack and Lem were best friends doesn't give their relationship justice, the author and I agree that they were life partners, not in a sexual manner but they were always there for each other. Lem was Jack's number #1 go-to guy and Jack was pretty much the love of Lem's life. They met in the 30's as teenagers in an all boy school. And as commonly known among gay men, straight boys will play around and would jack off in front of each other or have a masturbation circle. Now, the book details about a ritual if one boy wanted to engage with another boy, he would write a note on toilet paper because it is so easily disposable. Such a note from Lem to Jack existed and briefly mentioned by Jack in a letter to Lem, basically a off-the-collar rejection. No one knows what was written on the toilet paper but those two.
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Lem had his own room in the White House. The guards and secret service knew who he was and he had no pass the whole time he was there. Some people thought he was secret service. After Jack and Robert died, Lem put it on himself to educate the young Kennedys about Jack and Robert, because the older Kennedys felt talking about them when they were alive was too sad. Lem even took Bobby Jr. under his wing for a while. The Wikipedia article is just a few sentences and it does mention Jackie didn't want Lem around at the kids in the end because he was an alcoholic. The book doesn't mention this but it does mention that Lem did get depend on alcohol because he was depressed and heartbroken. Jackie and Lem's relationship was love and hate, sometimes they didn't get along but they got along because of their love for Jack. It is also little known that Lem was the one to encourage Jackie to refurnish the White House.
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The book does mentioned some men Lem was probably with, but no real details. There is one chapter that details about being gay in America, basic stuff I know about Stonewall; and how Lem did think about what impact it would be if he came out, being close to the Kennedys and all. He really wasn't a public figure, till today not many knew he was Jack's close friend. But back then, it might have made waves if people found out that the President's best friend was gay and had his own room in the White House. The chapter on gay life sort of makes up for the lack of mentioning of it in the middle of the book. The author is very open minded and handles the subjects of gender, sexual orientation and identity with dignity and respect. Lem died in 1981 of an heart attack at home and some believe his heart had been broken for a long time. Many personal friends said he was heart broken after Jack died, even more after Robert did. Lem's dying wish was for his casket to be carried and lowered in the plot by the Kennedy boys. When they arrived to the cemetery, they found the casket already in place. So to honor his memory, they took it out, took it around and then lowered in the plot. Jack and Lem's relationship wasn't scandalous or anything, but dependent. How Pitts eloquently puts it, theirs was a life partnership but not sexual. I think it shows how a great man Jack was, that his close friend was gay and he didn't matter to him.