--- title: Madonna Defends Rosie O'Donnell Against Donald Trump description: Following Donald Trump's renewed criticism of Rosie O'Donnell during the first presidential debate, Madonna stood up for her former costar. canonical: https://time.com/4509451/madonna-rosie-odonnell-donald-trump/ author: Megan McCluskey article:opinion: false article:content_tier: free article:published_time: 2016-09-27T15:39:06.000Z article:modified_time: 2026-10-07T06:48:31.553Z og:title: Madonna Defends Rosie O'Donnell Against Donald Trump og:description: "Cruelty never made anyone a winner" og:url: https://time.com/4509451/madonna-rosie-odonnell-donald-trump/ og:site_name: TIME og:image: https://static.time.com/v3/assets/bltea6093859af6183b/blt7a770f74341b0257/6988a7ae428a9e9579cd4678/rosie-odonnell-madonna.jpg?branch=production&width=594&quality=75&auto=webp&crop=16:9 og:image:width: 594 og:image:height: 334 og:image:alt: Madonna and Rosie O'Donnell Backstage at "Taboo" og:type: article twitter:card: summary_large_image twitter:title: Madonna Defends Rosie O'Donnell Against Donald Trump twitter:description: "Cruelty never made anyone a winner" twitter:image: https://static.time.com/v3/assets/bltea6093859af6183b/blt7a770f74341b0257/6988a7ae428a9e9579cd4678/rosie-odonnell-madonna.jpg?branch=production&width=594&quality=75&auto=webp&crop=16:9 ---  # Madonna Defends Rosie O'Donnell Against Donald Trump's Debate Comments > Sponsored content. 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Every edition is assembled by TIME editors rather than generated automatically. ### Sources * TIME Newsletters: [time.com/newsletters](/c/time-nl-brief-2026q3/newsletters?i=922b9c26-d84c-4a54-ae70-6d71e7e935a3&cr=time-nl-brief-2026q3-v1) ## Video: The Trump-Clinton Debate: the Interruptions [Watch (HLS stream): The Trump-Clinton Debate: the Interruptions](https://cdn.jwplayer.com/manifests/TfOQAjNY.m3u8) (1:50)  _Published 2016-09-27. Throughout the 90-minute debate, Trump exercised all the subtle put-downs familiar to almost any woman who has sat in a business meeting with a dismissive man. He interrupted Hillary Clinton more than 50 times, according to some estimates._  by [Megan McCluskey](https://time.com/author/megan-mccluskey/)  ## Megan McCluskey Staff Writer Sep 27, 2016 3:39 PM UTC  by [Megan McCluskey](https://time.com/author/megan-mccluskey/)  ## Megan McCluskey Staff Writer Sep 27, 2016 3:39 PM UTC [Donald Trump](http://time.com/4509300/donald-trump-hillary-clinton-presidential-debate-grade/) and [Rosie O’Donnell](http://time.com/3988748/rosie-odonnell-donald-trump/) have long been embroiled in a heated feud, but following the Republican nominee’s renewed criticism of O’Donnell during Monday’s [first presidential debate](http://time.com/4506217/presidential-debate-clinton-trump-survey/), Madonna came to the defense of her former costar. The 58-year-old singer took to Instagram early Tuesday morning to share a photo of herself and O’Donnell in 1992’s _A League of Their Own_ with a caption sticking up for her longtime friend. “Mess with my girl Rosie and you’re messing with me!!! Cruelty never made anyone a winner,” she wrote, adding the hashtag #rebelhearts4ever. The subject of O’Donnell was broached Monday when Hillary Clinton brought up Trump’s history of making misogynistic comments toward women, citing her opponent’s remarks about former Miss Universe [Alicia Machado](http://time.com/4509243/donald-trump-miss-universe-alicia-machado-piggy-housekeeping/). However, Trump responded by saying she deserved them. “Rosie O’Donnell, I said very tough things to her, and I think everybody would agree that she deserves it and nobody feels sorry for her,” he said. Trump has previously referred to O’Donnell as “[disgusting](https://www.youtube.com/watch?v=d32577Hom08),” a “[slob](https://www.youtube.com/watch?v=d32577Hom08)” and during the first Republican primary debate, a “[fat pig](http://time.com/3988748/rosie-odonnell-donald-trump/).” The feud originally began in 2006 when O’Donnell said Trump had gone bankrupt and called him a “snake-oil salesman” while [hosting _The View_](https://www.youtube.com/watch?v=64YhFQ99a-c). ## Transcript Actually that is - >> I will bring, excuse me. I will bring back jobs . >> I think a lot about what worked and how we can make it work again . >> Well, he approved NAFTA - >> We have 3 million new jobs, a balanced budget - >> Which is the single worst trade deal ever approved in this country . >> And incomes went up . >> No, no. You're telling the enemy everything you want to do . >> No we're not. No we're not - >> See you're telling the enemy everything you want to do . >> And I wrote about that In I wrote about- You called it the gold standard. Well, I hope I- You called it the gold standard of trade deals. You said it's the finest deal you've ever seen and- No, but when it was negotiated which I wrote about that it in my- So, is President Obama's fault? Is it President Obama's fault? Look before you even announced Look, there are different- Secretary is it President Obama's fault? But you have no plan. I do. Secretary you have no plan. In fact I have written a book about it. So for the next segment- Well look, can I just finish. I think I should. [ CROSSTALK ] You go to her website, then you take a look at her website. She's gonna raise taxes $ 1. 3 trillion. And there's nothing crazy. This is absolutely. About not letting companies bring their money back in to their country. So there is. You're wrong. You're wrong. No, I'm not. Murders are up. All right, you'll check. New York has done. You'll check. Donald supported the invasion of Iraq. Wrong. Wrong. Which has been proved, over and over again. Wrong. He actually advocates- What makes your- I did not support the war in Iraq. In 2002. That is is mainstream media nonsense put out by her- Question there, sense- Just, you, would you like to hear? Why is your, why is your judgment- I was against the war, wait a minute. I was against the way, - >> Any sense about this should be a concern . >> [ CROSSTALK ] Is getting a little bit old I must say, listen - >> It's a good one though, well described the problem . >> It's an accurate at all . >> Pregnancy as an inconvenience to employer? Who have said women don't deserve equal pay unless they do as good job as men . >> Secretary Clinton two minute please . >> Let's start the clock again Lester ```json [{"@context":"https://schema.org","@type":"NewsArticle","@id":"https://time.com/4509451/madonna-rosie-odonnell-donald-trump/","mainEntityOfPage":{"@type":"WebPage","@id":"https://time.com/4509451/madonna-rosie-odonnell-donald-trump/"},"headline":"Madonna Defends Rosie O'Donnell Against Donald Trump's Debate Comments","datePublished":"2016-09-27T15:39:06.000Z","dateModified":"2026-10-07T06:48:31.553Z","description":"\"Cruelty never made anyone a winner\"","url":"https://time.com/4509451/madonna-rosie-odonnell-donald-trump/","keywords":["Newsfeed","2016 Election","celebrities","Madonna","Donald Trump"],"thumbnailUrl":"https://static.time.com/v3/assets/bltea6093859af6183b/blt7a770f74341b0257/6988a7ae428a9e9579cd4678/rosie-odonnell-madonna.jpg?branch=production&width=1200&quality=75&auto=webp&crop=1200:675&height=675","author":[{"@type":"Person","name":"Megan McCluskey","jobTitle":"Staff Writer","url":"https://time.com/author/megan-mccluskey/"}],"articleSection":"","image":[{"@type":"ImageObject","url":"https://static.time.com/v3/assets/bltea6093859af6183b/blt7a770f74341b0257/6988a7ae428a9e9579cd4678/rosie-odonnell-madonna.jpg?branch=production&width=1200&quality=75&auto=webp&crop=1200:675&height=675","width":1200,"height":675,"headline":"Madonna and Rosie O'Donnell Backstage at \"Taboo\"","caption":"Rosie O'Donnell and Madonna during Madonna and Rosie O'Donnell Backstage at 'Taboo' at The Plymouth Theater in New York, New York, United States.","creditText":"Bruce Glikas/FilmMagic","representativeOfPage":true}],"publisher":{"@type":"Organization","name":"Time","url":"https://time.com/","logo":{"@type":"ImageObject","url":"https://time.com/images/logo.png","width":528,"height":156},"foundingDate":"March 3, 1923","sameAs":["https://www.facebook.com/time","https://www.instagram.com/time/?hl=en","https://twitter.com/time","https://www.pinterest.com/timemagazine"]}},{"@context":"https://schema.org","@type":"BreadcrumbList","itemListElement":[{"@type":"ListItem","position":1,"item":{"@id":"/tag/time-section-newsfeed/","name":"Newsfeed"}},{"@type":"ListItem","position":2,"item":{"@id":"https://time.com/4509451/madonna-rosie-odonnell-donald-trump/","name":"Madonna Defends Rosie O'Donnell Against Donald Trump's Debate Comments"}}]},{"@context":"https://schema.org","@type":"VideoObject","name":"The Trump-Clinton Debate: the Interruptions","description":"Throughout the 90-minute debate, Trump exercised all the subtle put-downs familiar to almost any woman who has sat in a business meeting with a dismissive man. 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