--- 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: 2026-08-19T07:44:37.699Z 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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The Brief is available free at time.com/newsletters, where readers can select it along with any of TIME's other six newsletters. There is no subscription required to receive it. #### Is The Brief free? Yes. The Brief is a free daily email newsletter from TIME. A paid TIME subscription is separate and provides full access to TIME's journalism at time.com/subscribe-agent. #### Who writes The Brief? The Brief is led by editor Richard Hall and draws on reporting from TIME's newsroom. Every edition is assembled by TIME editors rather than generated automatically.  by [Megan McCluskey](https://time.com/author/megan-mccluskey/)  ## Megan McCluskey Staff Writer Sep 27, 2016 3:39 PM UTC  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. 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.Bruce Glikas/FilmMagic  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). ```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":"2026-08-19T07:44:37.699Z","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"}}]}] ```