{"id":2331501,"date":"2026-03-16T16:23:26","date_gmt":"2026-03-16T16:23:26","guid":{"rendered":"https:\/\/celebrity.land\/en\/?p=2331501"},"modified":"2026-03-16T16:23:26","modified_gmt":"2026-03-16T16:23:26","slug":"what-a-wonderful-night-to-watch-kevin-oleary-lose-money","status":"publish","type":"post","link":"https:\/\/celebrity.land\/en\/what-a-wonderful-night-to-watch-kevin-oleary-lose-money\/","title":{"rendered":"What a Wonderful Night to Watch Kevin O\u2019Leary Lose Money"},"content":{"rendered":"<p><\/p>\n<div>\n<p>On Sunday night, as the <a rel=\"nofollow\" target=\"_blank\" href=\"https:\/\/www.jezebel.com\/oscars-2026-red-carpet\">Oscars red carpet<\/a> arrivals wound down, one film newbie lingered behind to get his moment\u2014probably because they don\u2019t roll out a red carpet on Shark Tank or during his frequent appearances on Fox News.<\/p>\n<p>Yes, Kevin O\u2019Leary was at the Oscars.\u00a0Because we\u2019ve lost all sense of decorum!\u2014and also because he had a supporting role\u00a0in Marty Supreme. In a red carpet <a rel=\"nofollow\" target=\"_blank\" href=\"https:\/\/variety.com\/2026\/film\/news\/kevin-oleary-defends-timothee-chalamet-ballet-opera-controversy-1236688841\/\">interview with Variety<\/a>, he revealed he\u2019d put $1,000 on his co-star Timoth\u00e9e Chalamet to win Best Actor. So you can imagine my glee when Michael B. Jordan took home the statue at the end of the night, leaving Marty Supreme empty-handed and O\u2019Leary out 1,000 bucks. I\u2019m sure $1,000 is the equivalent of a quarter in this guy\u2019s eyes, but hey, he still lost money. A win is a win!<\/p>\n<p>\u201c[Timothee\u2019s] a really great guy,\u201d O\u2019Leary told Variety. (Not the best look for Timmy when a registered asshole is rushing to your defense, but oh well.) \u201cI know the voting stopped long before <a rel=\"nofollow\" target=\"_blank\" href=\"https:\/\/www.jezebel.com\/theater-kid-timothee-chalamet-really-pissed-off-the-other-types-of-theater-kids\">that controversy<\/a> happened. The kid is a great kid. He took a bum rap on that. And by the way, gave a lot of promo to opera houses and ballet.\u201d<\/p>\n<p>True, but someone should have clued\u00a0O\u2019Leary in on a little internet theory called the Kardashian Curse\u2014an ongoing sports joke that says once an athlete starts dating a Kardashian, their career trends down. Think Tristan Thompson, Kris Humphries, Ben Simmons, Devin Booker, Lamar Odom\u2026 to name a few.\u00a0<span style=\"margin: 0px; padding: 0px;\">Chalamet, who\u2019s been dating Kylie Jenner for three years, was snubbed even after his hardcore campaign (almost begging) for the win,\u00a0plus after winning the category at the Golden Globes and Critics\u2019 Choice.<\/span><\/p>\n<p>Curse aside, we knew the category would be a toss-up. Chalamet was great in Marty Supreme, but every time O\u2019Leary appeared on screen, I felt rage. The sheer satisfaction he seemed to get from being in a movie was enough to root against the film.<\/p>\n<p>Plus, O\u2019Leary isn\u2019t a supporter of the arts, <a rel=\"nofollow\" target=\"_blank\" href=\"https:\/\/www.jezebel.com\/mark-ruffalo-billie-eilish-kevin-oleary-grammys\">telling celebrities<\/a> like Billie Eilish to \u201cshut your mouth and just entertain\u201d after her Grammy speech in which she said, \u201cno one is illegal on stolen land.\u201d Interesting advice considering he seems to have no problem opening his own mouth, especially on Fox News.<\/p>\n<p>Bonus shade: His Oscars outfit was, not even exaggerating, one of the most diabolical looks I have ever seen. It included a diamond-encrusted chain displaying the rare Triple Logoman NBA card, reportedly worth $30 million, which he flaunted like a toddler at show-and-tell.\u00a0<\/p>\n<p>There\u2019s an overwhelming sense of pride I feel watching these artists, surrounded by their peers, come together to honor each other\u2019s work and recognize the dedication it takes to advance their craft. And then there\u2019s O\u2019Leary: an infiltrator, a wolf in wolf\u2019s clothing\u2014or in this case, an ugly top.<\/p>\n<\/div>\n<p><em> \u2018 The preceding article may include information circulated by third parties \u2019 <\/em><\/p>\n<p><em> \u2018 Some details of this article were extracted from the following source www.jezebel.com \u2019 <\/em><\/p>\n","protected":false},"excerpt":{"rendered":"<p>On Sunday night, as the Oscars red carpet arrivals wound down, one film newbie lingered behind to get his moment\u2014probably because they don\u2019t roll out a red carpet on Shark Tank or during his frequent appearances on Fox News. Yes, Kevin O\u2019Leary was at the Oscars.\u00a0Because we\u2019ve lost all sense of decorum!\u2014and also because he [&hellip;]<\/p>\n","protected":false},"author":2,"featured_media":2331502,"comment_status":"open","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"om_disable_all_campaigns":false,"_jetpack_memberships_contains_paid_content":false,"jnews-multi-image_gallery":[],"jnews_single_post":[],"jnews_primary_category":[],"jnews_social_meta":[],"footnotes":""},"categories":[25173],"tags":[],"class_list":["post-2331501","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-artists"],"jetpack_featured_media_url":"https:\/\/celebrity.land\/en\/wp-content\/uploads\/2026\/03\/What-a-Wonderful-Night-to-Watch-Kevin-OLeary-Lose-Money.jpg","jetpack_sharing_enabled":true,"_links":{"self":[{"href":"https:\/\/celebrity.land\/en\/wp-json\/wp\/v2\/posts\/2331501","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/celebrity.land\/en\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/celebrity.land\/en\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/celebrity.land\/en\/wp-json\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/celebrity.land\/en\/wp-json\/wp\/v2\/comments?post=2331501"}],"version-history":[{"count":1,"href":"https:\/\/celebrity.land\/en\/wp-json\/wp\/v2\/posts\/2331501\/revisions"}],"predecessor-version":[{"id":2331503,"href":"https:\/\/celebrity.land\/en\/wp-json\/wp\/v2\/posts\/2331501\/revisions\/2331503"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/celebrity.land\/en\/wp-json\/wp\/v2\/media\/2331502"}],"wp:attachment":[{"href":"https:\/\/celebrity.land\/en\/wp-json\/wp\/v2\/media?parent=2331501"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/celebrity.land\/en\/wp-json\/wp\/v2\/categories?post=2331501"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/celebrity.land\/en\/wp-json\/wp\/v2\/tags?post=2331501"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}