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Tech May 14, 2026

Khosla Ventures Backs Ian Crosby's New AI Bookkeeping Venture Despite Bench Collapse

Khosla Ventures has invested $10 million in Synthetic, a new AI bookkeeping startup founded by Ian …
The Controversial Bet on AI BookkeepingDespite the collapse of his previous startup, Ian Crosby is taking another shot at building a business out of automating bookkeeping. His new venture, Synthetic, aims to create a fully autonomous AI bookkeeper that can generate accrual-based financials without direct human involvement.The Vision Behind SyntheticSynthetic is designed to revolutionize bookkeeping by eliminating the need for human accountants, a stark contrast to current accounting startups like Xero. Crosby maintains an all-or-nothing approach: "We're not going to release anything that's not fully autonomous. It's that or bust."The startup is currently in the design phase, with Crosby acknowledging that his vision may not yet be technologically possible. The company plans to initially serve only AI and other software startups.The $10 Million InvestmentDespite the challenges and Crosby's troubled past with Bench Accounting, Synthetic has successfully raised $10 million in a Seed funding round led by Khosla Ventures. The round also saw participation from Basis Set Ventures and Shopify CEO Tobias Lütke.This financial backing provides Crosby with the resources to wait for foundational AI models to become more reliable for bookkeeping calculations. "I've raised years of cash, so we can just wait it out," Crosby stated.Learning from Past FailuresKhosla partner Jon Chu defended the investment by explaining his tendency to "run towards controversy a little bit." He cited Parker Conrad's journey from Zenefits to founding Rippling (now valued at $17 billion) as an example of how industry narratives can be misleading.Chu conducted thorough due diligence, speaking with several executives who worked with Crosby after his departure from Bench. According to Chu, they "had fantastic things to say about Ian." This feedback, combined with Crosby's subsequent roles at Shopify and founding of Teal (which was acquired by Mercury), convinced Khosla of his growth potential.The Bench Accounting FalloutCrosby's previous venture, Bench Accounting, famously shut down in 2024 before being "bought for scraps." Crosby maintains he wasn't directly responsible for bringing the company to insolvency, stating he was fired by Bench's board in 2021 after turning down a $250 million acquisition offer from Brex.The board reportedly disagreed with Crosby's strategic direction as the business was bleeding cash, and his executive team was frustrated with his direct leadership style. "He took a big swing, made a few mistakes. That didn't go well," Chu acknowledged about Crosby's tenure at Bench.The Path to Autonomous AI BookkeepingWhile Synthetic's prototype works for a narrow group of users, Crosby remains uncertain how it will scale for a broader customer base. He compared the current state of AI bookkeeping to "a self-driving car that can drive down one street versus the self-driving car that can drive down any street.""We haven't driven down enough streets to know if it's going to crash," Crosby explained, highlighting the technical challenges ahead. Despite these obstacles, the founder remains committed to his vision of a fully automated financial future.
#Khosla Ventures #Ian Crosby #Synthetic
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Sports May 14, 2026

Alexander Bublik: The Honest Rebel Redefining Professional Tennis

Alexander Bublik, known for his candid and often controversial takes on tennis, has transformed fro…
The Candid Champion's Career TransformationThere are few experiences on the professional tennis circuit more uncomfortable than being Alexander Bublik's opponent. The task of deciphering one of the more talented and unpredictable players is challenging enough, but there is also a risk of being on the receiving end of a few stinging insults. Over the years, Bublik has become notorious among Russian-speaking fans for his scathing rants about his rivals, while reserving plenty of scorn for himself and the sport as a whole.From Underachiever to Top Ten: Bublik's Remarkable RiseThis past year has marked a significant transformation for the Russian-born Kazakhstani player. Just twelve months ago, Bublik had fallen out of the top 80 and his dire form forced him to drop back down to the ATP Challenger circuit—a desperate low for someone already considered an underachiever. However, his enviable talent has propelled a rapid turnaround: Bublik ended the clay-court season by defeating Alex de Minaur and Jack Draper (ranked No 9 and No 5), en route to his first grand slam quarter-final at the French Open. He then toppled the world No 1 Jannik Sinner on his way to winning the ATP 500 title in Halle.The Financial Reality of Professional TennisWhile most millionaire players are hesitant to speak about their earnings, money is another subject that Bublik often speaks freely on. "I think you realise that quickly once you start making your first money playing tennis that it's a big business," he says. "It's nice to win trophies, it's nice to be playing in a beautiful arena, it's all nice but at the end of the day you got to pay yourself and I think that was the very first motivation that I had when I became a professional tennis player." This pragmatic approach to tennis as a business has been central to his career strategy, even during his less committed years.The Changing Landscape of Tennis AuthenticityBublik's outspoken nature has sparked debate about authenticity in professional sports. "I think emotions are emotions," Bublik explains. "I guess it's just we live in a world where everyone tries to fake and I think there's nothing wrong in just releasing your emotions in a way because it's a stressful sport." His perspective extends to social media as well: "I guess the entire social media is fake, so I guess all the people who are there pretending to be someone they're not. I guess it's fake." This stance positions Bublik as a counterpoint to the carefully curated public personas common in modern sports.Maintaining Momentum: The Challenges AheadReaching the top 10 is impressive, but as Bublik's recent defeat at the Italian Open demonstrates, it is far tougher to maintain that status week in, week out. The top players have targets on their backs and it is far easier to swing freely with nothing to lose. Bublik will have a significant amount of points to defend over the coming months, starting with his return to Roland Garros one year on from the most beautiful moment of his career. His handling of these new experiences will say plenty about whether his transformation is complete or merely a remarkable career resurgence.
#Alexander Bublik #Professional Tennis #ATP Tour
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Politics May 14, 2026

Federal Judge Blocks US Sanctions Against UN Palestinian Territory Rapporteur

A federal judge has temporarily blocked US sanctions against UN Special Rapporteur Francesca Albane…
The Legal Victory Against Political SanctionsA federal judge has temporarily blocked United States sanctions against Francesca Albanese, a United Nations expert on the occupied Palestinian territory. UN Human Rights Council Special Rapporteur Francesca Albanese was originally sanctioned in July 2025 after she publicly criticized Washington's policy on Israel's war against Palestinians in Gaza.Albanese's husband and daughter filed a lawsuit in February against the Trump administration over the sanctions, arguing that they were an effort to punish her for bringing attention to Israel's rights abuses against Palestinians. In his court order on Wednesday, US District Judge Richard Leon granted a preliminary injunction against the sanctions.Judge's Reasoning: Protecting Free SpeechJudge Leon found that the Trump administration sought to regulate Albanese's speech because of the "idea or message expressed." In his memorandum opinion, he wrote: "Albanese has done nothing more than speak. It is undisputed that her recommendations have no binding effect on the ICC's actions – they are nothing more than her opinion."The sanctions had barred the Italian lawyer and human rights expert from entering the US, using US banks and payment systems, and prevented anyone else in the US from doing business with her. Albanese's family claimed in the lawsuit that the sanctions were "effectively debanking her and making it nearly impossible to meet the needs of her daily life."Background on the SanctionsSince 2022, Albanese, a legal scholar, has served as the special rapporteur for the West Bank and Gaza, where she monitors human rights abuses against Palestinians. The UN Human Rights Council selected her for this position.The Trump administration sanctioned her last July, calling her "unfit" for her role and accusing her of "biased and malicious activities" against the US and its ally, Israel. Albanese had also recommended that the International Criminal Court (ICC) pursue war crimes prosecutions against Israeli and US nationals.International Reactions and SignificanceAlbanese, who said the US sanctions were "calculated to weaken my mission" when they were first imposed, celebrated the ruling on social media. "Thanks to my daughter and my husband for stepping up to defend me, and everyone who has helped so far," Albanese said in a statement on X. "Together we are One."The ruling represents a significant check on the administration's ability to use financial sanctions against international officials who express critical viewpoints. It establishes that such sanctions cannot be used as a tool to suppress speech that critical of US foreign policy, particularly regarding the Israeli-Palestinian conflict.What Happens NextThe preliminary injunction is temporary, and the Trump administration is likely to appeal the decision. The case will proceed through the legal system, with arguments focusing on the balance between national security interests and free speech protections for international officials.Meanwhile, Albanese can continue her work as UN rapporteur without the immediate threat of US sanctions. Her case has drawn international attention to the use of sanctions against human rights advocates and may influence how similar cases are handled in the future.
#Francesca Albanese #UN Human Rights Council #US Sanctions
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Art May 14, 2026

Famous Image of JMW Turner Not a Self-Portrait, Expert Claims

A leading expert, Dr. James Hamilton, claims that the most famous image of JMW Turner is not a self…
The Controversy Surrounding Turner's Portrait In 2020, Tate Britain hosted the launch of a new £20 banknote bearing representations of The Fighting Temeraire by JMW Turner and the artist's most famous self-portrait. However, a leading expert, Dr. James Hamilton, has now claimed that the latter work, part of the Tate collection, is not by Turner at all. The Expert's Investigation Hamilton, who has published books on Turner and staged exhibitions at museums and galleries nationwide, said that while the painting does depict the English Romantic painter, it is likely to be the work of his contemporary, John Opie. Hamilton told the Guardian he started researching the portrait because “there’s nothing else like it in Turner’s work”. The Attribution Debate Hamilton believes the portrait was misattributed after being included among nearly 300 oil paintings and 30,000 sketches and watercolours in the Turner Bequest following the artist’s death in 1851. He concluded that stylistic evidence points to Opie, who depicted his sitters in a similar “light emerging dramatically from dark”. The Impact on Turner's Legacy The painting, dated c1799 when Turner was 24, was created by a master portrait painter with “brilliant dexterity”, Hamilton added. If Hamilton's claims are correct, it could have significant implications for Turner's legacy and the art world's understanding of his work. The Future of the Portrait's Attribution A Tate spokesperson said: “As the home of the Turner Bequest, we always welcome new ideas about Turner’s life and new interpretations of his work. We look forward to exploring James Hamilton’s research further.”
#JMW Turner #John Opie #Tate Britain
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Sports May 14, 2026

Iran's World Cup Squad Receives Public Sendoff Amid Visa Concerns for US Tournament

Iran's national football team received a massive public sendoff in Tehran ahead of their participat…
The LeadIran's national football team, Team Melli, was given a grand sendoff by thousands of fans in Tehran's Enqelab Square as they prepare to travel to the United States for the 2026 FIFA World Cup. The celebration comes amid significant political concerns about whether the Iranian delegation will be able to enter the US due to tensions between the two nations and the IRGC's designation as a terrorist entity.The Public CelebrationThe departure rally witnessed an enthusiastic crowd cheering for the players as they made patriotic statements from a stage on May 13, 2026. The event marked the unveiling of Iran's new World Cup 2026 kit. Mehdi Taj, president of the Football Federation Islamic Republic of Iran (FFIRI), described it as "the best sendoff in the last four World Cup campaigns.""The players are with the people, and the crowd stands with the country's dignity, honour, and strength. Whatever the result, may Iran's flag be raised there and defended," Taj told state TV, emphasizing the national significance of the team's participation.The Political HurdlesIran's participation in the World Cup has been in question since the US and Israel attacked Iran, starting a regional war on February 28. The concerns were further amplified when an FFIRI delegation, led by Taj, was turned back at Toronto's main airport, citing "unacceptable behaviour of immigration officials" despite holding valid visas.In 2024, Canada listed Iran's Islamic Revolutionary Guard Corps as a terrorist organisation, and statements from the Canadian government indicated that Taj was denied entry due to his alleged ties with the IRGC. Similar concerns exist for the US, where the IRGC is also classified as a "terrorist entity," and Secretary of State Marco Rubio has stated that no one with ties to the organisation would be admitted to the country.The World Cup PreparationDespite the political uncertainties, Iran is proceeding with its World Cup preparations. Following the sendoff event, the team will travel to Turkiye to continue training at a camp. Iran has scheduled a World Cup warm-up match against The Gambia in Antalya on May 29, with the FFIRI in the process of arranging another friendly during their time in Turkiye.Iran is scheduled to be based in Tucson, Arizona during the World Cup and will face New Zealand, Belgium, and Egypt in Group G. The Iranians will open their World Cup campaign against New Zealand in Los Angeles on June 15.The FIFA InterventionIran has placed responsibility for getting the players and team officials into the US firmly in the hands of FIFA. "Nothing has arrived yet regarding the visas. We hope it will definitely be handled within this timeframe," Hedayat Mombeini, FFIRI secretary-general, told state TV at the rally."FIFA has made promises, and hopefully those promises will lead to results, and the players will receive their visas on time," Mombeini added, highlighting the football governing body's role in navigating the diplomatic challenges. FIFA has insisted for weeks that Iran will take part in the tournament, positioning itself as a diplomatic mediator in the situation.
#Iran #FIFA World Cup #United States
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Entertainment May 13, 2026

Carla Simón: Filmmaking Through Family, Loss and the Legacy of Aids

Spanish filmmaker Carla Simón discusses her approach to creating deeply personal films that explore…
The Lead: Carla Simón's Unique Approach to Family DramaFamily reunions in European arthouse cinema are almost always unhappy events, on a scale of strife that ranges from simmering resentment to spectacular score-settling. Carla Simón, however, has a rare gift: she makes you leave the cinema with renewed faith that having relatives and keeping in touch with them may actually be a wonderful thing.No film-maker working in Europe now is as capable of turning birthday gatherings, garden parties or poolside barbecues into thrillingly sprawling canvases of human virtue and vice as this 39-year-old rising star. From a riotous water fight in the Berlinale Golden Bear-winning farming drama Alcarràs to a foul-mouthed dinner table singalong in her new film Romería, Simón directs kinship meetings with the attention to detail that other film-makers may invest in action sequences or dance routines.The Event Details: Romería and the Journey to Self-DiscoveryAmong the tricks Simón employs, she explains, is to ensure her actors only read the script once before the camera starts rolling, so they have to improvise to fill the gaps. She takes her casts to parties, for walks and on shopping trips, and if there are disagreements on the way, so much the better. The ultimate secret sauce, though, is to ignore WC Fields's notorious advice and always work with children and animals."I never get bored of working with kids," she says. "When you are only working with adult actors, shooting becomes more like executing an idea that you have in your mind, and I think that is not interesting. With children, you always have this feeling that that things are going to happen in front of the camera by chance. It keeps things alive."Her new film Romería, meaning "pilgrimage" in Spanish, dives deeper into the story of the biological parents she barely got to know. Eighteen-year-old Marina travels to her relatives in Vigo, in north-western Galicia, purportedly to find the death certificate of her biological father, which she needs to study film-making in Barcelona. The initial reaction is warm, but family is a room with dark corners and locked closets.The Personal Journey: Aids, Loss and Family SecretsSimón's fascination with freewheeling scenes of family life was undoubtedly honed through her own biography. Born in Barcelona in 1986, her father died when she was three and her mother when she was six. Both of them succumbed to Aids. She was 12 when her adoptive mother told her that her parents had been infected with the autoimmune disease through their use of drugs.All of her first three films have been strongly autobiographical: Summer 1993 tells the story of a six-year-old girl who moves to an unspecified location countryside to live with her aunt after the death of her mother, while 2022's Alcarràs is specifically set in the Catalan peach-growing community of her adoptive family.In the film, a cache of letters written by her late mother opens up a portal to the time when her parents met and discovered love – for each other, the Atlantic Ocean and drugs. The letters, Simón explains, are real. "She wrote to her friends and family while she lived in Vigo. Her Catalan is full of mistakes, because teaching Catalan was banned under the Franco regime. But they are the most important thing that I have from my mother, because suddenly I can hear her talking."The Impact Analysis: Spanish Cinema and the Legacy of AidsSpanish cinema has a track record in making films where child actors take centre stage: Ana Torrent's spell-binding turn as a young girl obsessed with the Frankenstein tale in Víctor Erice's 1973 film The Spirit of the Beehive is considered an all-time great performance by a minor, and Simón describes it as "a very, very important film for me".During the transition period after Franco's rule, Madrid gave birth to la movida, a countercultural movement that celebrated lifestyles that had been banned under military rule. "All these kids who were raised under Franco and religious oppression, suddenly freedom arrived and they embraced it", Simón says. "They didn't think much about the future or the consequences of what they were experimenting with. And then the drugs came in."When we talk about this generation in Spain, people sometimes use words like shame and blame, but I feel that's really unfair: people like my parents just had bad luck.The Future Direction: Beyond Family in Simón's Next ProjectHalfway through Romería there is a stylistic shift, from the Eurorealism she favoured in her previous works toward something more magical-realist: there is a mysterious cat you might expect to encounter in a Miyazaki film, and an unforgettable dance number set to Vigo punk rocker's Siniestro Total's song Bailaré Sobre Tu Tumba ("I'll Dance on Your Grave")."These three films I've made are kind of a cycle, because they all talk about my family, adoptive and biological. But since I became a mother a few years ago, I feel that my place in the family changed. When you have kids you feel it's a new period in your life, so I feel like maybe doing something that has nothing to do with my family."Her next film, she confides, is going to be a flamenco musical.
#Carla Simón #Romería #Spanish cinema
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Entertainment May 13, 2026

Cannes: The Beautiful Grueling Circus That Defines Cinema

Agnès Poirier reflects on the Cannes Film Festival as a unique, exhausting yet magical experience t…
The Unparalleled Experience of CannesNothing prepares you for the shock that is the Cannes film festival: the adrenaline, the fatigue, the elation and the emotion, but also the hunger, the anger, the magic and the ridicule. For young cinephiles, and for almost everybody who works in the film industry, it is the mecca of cinema and has been so for nearly eight decades. Anyone going for the first time this week, as I did 25 years ago, should not listen to the old grognards – Cannes' battle-worn veterans – who will lament that the festival has become an abominable circus and swear this year will be their last. It is a circus, and you can bet they will be back for as long as their knees can take it. For there is nothing quite like it.From Resistance to Global Cinema HubBorn to counteract Benito Mussolini's Venice film festival, its first edition was planned for September 1939, but Adolf Hitler had other plans. The previous year, under pressure from Berlin and Rome, the Venice film festival's top prize, the Coppa Mussolini, was handed to Leni Riefenstahl's propaganda film Olympia, prompting the French, British and American delegates to walk out. Hence Cannes, conceived as the festival of the "free world". More than 80 years later, for all its sins, it has remained faithful to that founding promise.The Expansive Scale of Modern CannesOver the decades, Cannes has mutated into an ever-hungrier mammoth, needing more space, and more venues, as it attracts an increasing number of journalists and professionals. A purpose-built Palais des Festivals had to be erected in the 1980s. "The bunker", as we have come to call it, is not exactly beautiful but brutally efficient at managing Cannes' mind-boggling crowds. This year, about 40,000 accredited festival-goers are descending on the French Riviera from 140 different countries, with dozens of films selected across all sidebars. At the same time, the Marché du Film, running alongside the festival since the late 1960s, is gathering about 16,000 participants, with thousands of films and projects up for sale. Cannes is both a summit for the cinema elite and a giant film bazaar.Three Worlds Colliding at La CroisetteFor 11 days in May, three different worlds lead parallel lives – critics, deal-makers and red-carpet royalty – colliding almost by accident on the seafront boulevard known as La Croisette. Hundreds of critics watch multiple films a day with monastic discipline. When they give in to parties, they bitterly regret it the next morning. You can spot some of us sleeping through entire screenings; how some colleagues manage to review films is a mystery. I remember a well-known French critic who had such vivid dreams in the darkness that he became convinced they were scenes in the films. His reviews were full of brilliant analysis of moments that did not exist.We critics rush between screenings, press conferences, interviews, our desks and the bunker's free espresso machines, often forgetting to eat or even pee. Downstairs, in the bunker's basement, and in hotel suites and rented apartments, the film market runs day and night: buyers juggle numbers, producers charm, directors and screenwriters fight for their vision. Above them floats Cannes' top layer – stars and "talent" spending hours in hair and makeup before climbing the 24 steps of the red carpet in borrowed couture and jewellery. When people in the industry groan, "oh God, it's Cannes again", it is this collision of financial anxiety, choreographed glamour and sheer exhaustion they are bracing themselves for.The Magic and Meaning Behind the GlamourThese worlds sometimes collide in the most poetic or grotesque ways. One morning, rushing to my first screening at 7.30am, I was walking along the Croisette when I saw, coming towards me, slightly dishevelled in a tuxedo, Jack Nicholson on his way back to his hotel after a long night. I smiled, he smiled back. He was alone, no bodyguards, no chaperones. Those were the days. I also shared a lift with Takeshi Kitano in full samurai attire, and I will never forget turning into a hotel corridor and finding myself nose to nose with Max von Sydow – Ingmar Bergman's medieval knight from The Seventh Seal. My cinephile heart skipped a beat.One of my favourite sidebars in Cannes, alongside the competition where you watch the year's best crop of films, is Cannes Classics, showing restored world masterpieces and documentaries about cinema. I always start the festival there: it is the best way to reset and begin afresh. Then I am ready for the 10-day onslaught of motion pictures, and for the magic moment that precedes each Cannes screening – the festival's own jingle, a palm ascending the red carpet from underwater and then into the sky, lifted by the ethereal arpeggios of Camille Saint-Saëns's Carnival of the Animals.Cannes: Enduring Symbol of Cinematic ResistanceIn 1955, Cannes gave its first official Palme d'Or to Delbert Mann's Marty; half a century later I found myself befriending its wonderful star, Betsy Blair, on the Croisette. I had the joy of seeing Ken Loach twice climbing those steps to collect the Palme, escorted by police outriders from Nice airport as if he were a head of state. I watched Iranian directors Jafar Panahi and Mohammad Rasoulof showing films at peril to their lives. For all the craziness of the red carpet and the samurai outfits, Cannes never forgets that it was founded as a gesture of resistance. That, as much as the glamour and the exhaustion, is why we keep going back.
#Cannes Film Festival #Agnès Poirier #cinema
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Tech May 12, 2026

Google Brings Agentic AI and Vibe-Coded Widgets to Android

Google announced new Gemini Intelligence AI features for Android, including agentic capabilities th…
The Lead: Google's Android AI RevolutionGoogle announced a significant upgrade to its Android operating system at the "Android Show: I/O Edition" event, introducing new Gemini Intelligence-branded AI features that transform how users interact with their devices. These innovations include agentic AI capabilities that can complete complex, multi-step tasks across different apps, as well as a novel "vibe coding" feature that allows users to create custom widgets using natural language descriptions.The Event Details: Agentic AI Capabilities ExpandGoogle's new agentic AI features represent a significant leap forward for digital assistants. The system can now handle multistep processes like copying a grocery list from notes and adding items to a shopping cart. Users activate these features by pressing the phone's power button and describing the task they want to accomplish, with the phone's screen providing context for the assistant. Notably, Gemini will wait for final confirmation before completing actions like checkout, ensuring user control throughout the process.The company had previously introduced some agentic capabilities at the Samsung Galaxy S26 launch, including the ability to book a front-row bike for a spin class or find a class syllabus in Gmail and then search for related books. These capabilities have now been expanded to handle more complex, cross-application workflows.The Data Analysis: Market Expansion TimelineGoogle has provided a clear rollout timeline for these new features. The agentic AI capabilities and vibe-coded widgets will first become available on the latest Samsung Galaxy and Google Pixel devices this summer. The company plans to expand these features to other Android devices later in the year, indicating a phased approach to market penetration.Additionally, specific features like Gemini in Chrome will arrive in late June, allowing users to summarize webpage content or ask questions about online material. This mirrors the functionality already available on desktop versions of Chrome with Gemini integration.The Impact Analysis: Redefining User InteractionThese developments mark a fundamental shift in how users interact with their mobile devices. By enabling AI to understand and execute multi-step processes across different applications, Google is moving beyond simple task completion to creating a more seamless, intelligent user experience. This could potentially reduce the cognitive load on users by automating complex workflows that previously required manual intervention across multiple apps.The introduction of "vibe coding" for widget creation represents another significant innovation. By allowing users to describe widgets in natural language, Google is lowering the barrier to customization and making personalization more accessible to non-technical users. This approach mirrors similar efforts by other companies like Nothing, which released a similar tool last year, but Google's implementation is deeply integrated into the Android ecosystem.The Prediction: The Future of AI on AndroidAs these AI capabilities become more sophisticated and widespread, we can expect to see a fundamental transformation of the Android user experience. The line between applications may continue to blur as AI increasingly manages interactions between different services. This could lead to new opportunities for developers to create more specialized tools that work in concert with Google's agentic AI.Google's commitment to following its Material 3 expressive design language across these AI features suggests a cohesive vision for the future of Android aesthetics. As competition in the AI space intensifies, these innovations may set a new standard for what users expect from their mobile devices, potentially accelerating the adoption of AI-powered personal assistants across the industry.
#Google #Android #Gemini
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Sports May 11, 2026

Maldini's Legacy Haunts Struggling Milan as Champions League Dreams Fade

AC Milan's form has collapsed with just seven points from their last eight games, leaving their Cha…
The Collapse of a European GiantThere were more than seven minutes left to play in a crucial end-of-season match, yet San Siro was already half empty. Milan's Ultras had deserted the Curva Sud to prepare a post-game protest, but even the more forgiving parts of the club's fanbase could not be bothered to stay until the end of another humiliating defeat. Their team was losing 3-0, at home, to Atalanta, and it hardly even felt a surprise.With this loss, inevitable as it now appeared, the Rossoneri had collected just seven points from their last eight games. Only three teams in Serie A had done worse over the same stretch. Two of those – Verona, and Pisa – have been relegated. The third, Lecce, are perilously close to joining them.The Maldini Factor and Management DecisionsWatching their beleaguered team struggle to get the ball out from the back against Atalanta's persistent press, fans started to sing for Paolo Maldini. One of the all-time great defenders, he won seven Serie A titles and five Champions Leagues as a player, extending the legacy of success begun by his father, Cesare.Appointed as a director for sporting strategy and development by Milan's then owners, Elliott Management, in 2018, Maldini was promoted to technical director a year later. He played a central role in player recruitment, helping build the team that won Serie A in 2021-22 – the club's first Scudetto for 11 years.Maldini's position was initially confirmed after RedBird Capital bought Milan in 2022. But he was fired one year later, despite having just overseen a fourth-place finish. The Rossoneri had just finished fourth, and Maldini spoke about a need for further squad investment to stay competitive at the highest level. But Milan's most expensive signing of the previous summer, Charles De Ketelaere, had been a flop, and their new CEO Giorgio Furlani said the objective given to him by RedBird was to get the club "living within our means."The Summer Investment and Early PromiseThe appointment of Massimiliano Allegri this summer was supposed to get things back on track. Here was a man defined by Italy's sporting press as a "guarantee" of Champions League football. An aggressive summer transfer window followed, headlined by the arrival of Luka Modric, and featuring significant outlays on the likes of Christopher Nkunku, Ardon Jashari, Samuele Ricci, Koni De Winter, Adrien Rabiot and Pervis Estupiñán.With no European distractions, Milan looked well equipped for a strong domestic campaign. Up until March, they delivered. The performance to beat Inter was classic Allegri, controlling the game while surrendering possession. Estupiñán scored before half-time, and Milan barely gave their opponents a sniff after that. This had been the mode all season: just win, it does not need to be pretty.The Tactical Breakdown and Player IssuesBut the problem with focusing always on the outcome is that you have nothing to fall back on once that part goes wrong. Milan's form early this season was built on the performances of talented individuals – Modric, certainly, but also Rabiot and especially Christian Pulisic, who had eight goals and two assists in the league, despite missing five games, by the end of December.Allegri's innovation was to move the American inside to operate as a centre-forward. He pulled the same trick with Rafael Leão after the Portuguese returned from a calf injury. Both thrived at first, but as their goals tailed off, Milan have struggled to replace them. Too many square pegs forced into round holes? Or is the picture a little more nuanced? Both Pulisic and Leão have been affected by physical issues as the season progressed.Atalanta were excellent, pressing selectively and executing ruthlessly. Giacomo Raspadori, signed from Atlético Madrid in January, brought a typically high-energy bustle behind the attack and it was his blocked shot that rebounded to Éderson inside the box for the opener. Nikola Krstovic, in the No 9 role, pinned his man expertly before laying the ball off to Davide Zappacosta to make it 2-0 before half-time.Fan Protests and Management ResponseWhat stood out in these moments was the clarity of purpose: each player performing the role they are best suited to and understanding what was required. The contrast with Milan's disjointed assembly of talents was stark. Absent the injured Modric, there was no glue to bind them together.Ultras had already made their feelings known before kick-off with a protest outside the ground then a choreography in the Curva Sud, using their bodies and mobile phone flashlights to spell out the letters "G.F. OUT" – Furlani's initials. Reporters saw a pair of fans attempt a protest, holding up shirts with Maldini's name on the back in front of the section where executives sit, but stewards ushered them away.By leaving early, they almost missed an improbable turnaround. Milan pulled a goal back in the 88th minute, Strahinja Pavlovic heading home from a Ricci free-kick. Nkunku, on as a second-half substitute, then won and converted a penalty. Suddenly the deficit was down to one goal. In the seventh minute of injury time, Matteo Gabbia almost equalised, flashing a header wide from another set-piece.Uncertain Future for Italian Football's PowerhouseMilan exist in a different orbit, still fourth in the table, even if their grip on a Champions League spot looks very loose indeed. It feels absurd to say it now, but before this miserable run they were the team keeping the Serie A title race alive. They were the last team to beat Inter, since crowned as champions, on 8 March. The gap between them, with mocking symmetry, was seven points.The layers to these decisions are complex, each party with their own version of how working relationships grew strained. But Maldini's assessment resonated with fans who want to see their team fight for trophies. Milan finished second in 2023-24 but fell all the way to eighth last season, and now find themselves once again struggling to maintain their position among Europe's elite.With the season approaching its conclusion, the question remains whether this is merely a temporary setback or a sign of deeper structural issues at the club. The contrast between the clear, purposeful football of Atalanta and Milan's disjointed performance suggests that tactical clarity may be as much a problem as player quality or management decisions.
#AC Milan #Paolo Maldini #Serie A
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