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Sean ‘Diddy’ Combs timeline: From one of hip-hop’s most nimble entrepreneurs to prostitution-related convictions

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For more than two decades, Sean “Diddy” Combs was one of hip-hop’s most nimble entrepreneurs, spinning his hitmaking talents into a broad business empire that included a record label, a fashion brand, a TV network, deals with liquor companies and a key role in a reality TV show.

Then he was charged with forcing, threatening and manipulating two ex-girlfriends into drug-fueled sex marathons, with assistance from a network of associates.

Combs denied the allegations and went to trial in a high-stakes federal sex crimes and racketeering case. The trial ended Wednesday with a verdict that his attorneys called a victory: Combs was convicted of prostitution-related offenses but acquitted of higher-level charges of racketeering and sex trafficking.

Here is a timeline of major events in his life story:

1990-1999

1990: Combs, then a student at Howard University, gets his start in the music business with an internship at Uptown Records in New York.

Dec. 28, 1991: Nine people die at a celebrity basketball game promoted by Combs and the rapper Heavy D when thousands of fans try to get into a gym at the City College of New York. A mayoral report lays part of the blame for the catastrophe on poor planning by Combs.

1992: Combs is one of the executive producers on Mary J. Blige’s debut album, “What’s the 411?”

1993: After being fired by Uptown, Combs establishes his own label, Bad Boy, which quickly cuts a lucrative deal with Arista Records.

1994: Bad Boy releases Notorious B.I.G.’s album “Ready to Die.” Two months later, Tupac Shakur survives a shooting in New York and accuses Combs and Biggie of having prior knowledge of the attack, which they deny. Shakur was later killed in a 1996 shooting in Las Vegas.

1996: Combs is convicted of criminal mischief after he allegedly threatened a photographer with a gun.

1997: Biggie is killed in Los Angeles. Combs, then known as Puff Daddy, releases “I’ll be Missing You” in honor of his dead star.

1998: Combs wins two Grammys, one for best rap album for his debut “No Way Out” and another for best rap performance by a duo or group for “I’ll Be Missing You” with Faith Evans. Also that year, Combs’ Sean John fashion line is founded.

April 16, 1999: Combs and his bodyguards are charged with attacking Interscope Records music executive Steve Stoute in his New York office in a dispute over a music video. Combs is sentenced to an anger management course.

Dec. 27, 1999: Combs is arrested on gun possession charges after he and his girlfriend at the time, Jennifer Lopez, fled a shooting that wounded three people at a New York City nightclub. Some witnesses tell police Combs was among the people shooting in the club. He is later charged with offering his driver $50,000 to claim ownership of the 9 mm handgun found in his car.

2001-2008

March 17, 2001: Combs is acquitted of all charges related to the nightclub shooting. One of his rap protégés, Jamal “Shyne” Barrow, is convicted in the shooting and serves nearly nine years in prison. Two weeks after the trial, Combs announces he wants to be known as P. Diddy. (Barrow also later changed his name, to Moses Barrow, and became a parliamentarian in his native Belize).

2002: Combs becomes the producer and star of “Making the Band,” a talent search TV show.

Feb. 1, 2004: Combs performs at the Super Bowl halftime show along with Janet Jackson, Justin Timberlake and others. A week later, Combs, Nelly and Murphy Lee win a Grammy for best rap performance by a duo or group for “Shake Ya Tailfeather.”

April 2004: Combs makes his Broadway acting debut in “A Raisin in the Sun.”

2005: Combs announces he is changing his stage name to Diddy, getting rid of the P.

March 2008: Combs settles a lawsuit brought by a man who claims Combs punched him after a post-Oscar party outside a Hollywood hotel the previous year. In May, Combs is honored with a star on the Hollywood Walk of Fame.

2015-2022

2015: Combs is arrested after a confrontation on the campus of UCLA, where one of his sons played football. Assault charges are later dropped.

2016: Combs launches a Harlem charter school, the Capital Preparatory School. Also that year, he announces he is donating $1 million to Howard University.

2017: Combs is named the top earner on Forbes’ list of the 100 highest-paid celebrities, which says he brought in $130 million in a single year.

2018: Kim Porter, Combs’ former girlfriend and the mother of three of his children, dies from pneumonia at age 47.

2022: Combs receives a lifetime honor at the BET Awards.

2023-2025

Sept. 15, 2023: Combs releases “The Love Album — Off the Grid,” his first solo studio project since 2006’s chart-topping “Press Play.”

Nov. 16, 2023: R&B singer Cassie sues Combs, alleging that during their decade-plus as a couple, he subjected her to abuse, including beatings and rape. A day later, the lawsuit is settled under undisclosed terms. Combs, through his attorney, denies the accusations.

Nov. 23, 2023: Two more women accuse Combs of sexual abuse in lawsuits. Combs’ attorneys call the allegations false. Dozens of additional lawsuits follow by women and men who accuse Combs of rape, sexual assault and other attacks. Plaintiffs include singer Dawn Richard, a “Making the Band” contestant who alleged years of psychological and physical abuse. Combs denies all the allegations.

March 25, 2024: Federal agents search Combs’ homes in Los Angeles and Miami Beach, Florida.

May 17, 2024: CNN airs video that shows Combs attacking and beating Cassie in a Los Angeles hotel hallway in 2016. Two days later, Combs posts videos on social media apologizing for the assault.

Sept. 16, 2024: Combs is arrested at his Manhattan hotel. A federal sex trafficking and racketeering indictment unsealed the next day accuses him of using his business empire to coerce women into participating in sexual performances. Combs denies the allegations. His attorney calls it an unjust prosecution of an “imperfect person.”

May 5, 2025: Jury selection begins for Combs’ trial.

May 12, 2025: A jury is selected and testimony begins in Combs’ trial.

June 30, 2025: Jury deliberations begin in Combs’ trial.

July 2, 2025: The jury convicts Combs of two counts of a prostitution-related offense but acquits him of higher-level charges of racketeering and sex trafficking. The outcome significantly reduces the rap mogul’s potential prison sentence, which a judge will determine in the months to come. His lawyers unsuccessfully ask for him to be released on bond in the meantime. Combs is visibly relieved by the verdict, and his lead lawyer calls it “a victory of all victories.”



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JetBlue flight near Venezuela avoids midair collision with U.S. Air Force tanker

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A JetBlue flight from the small Caribbean nation of Curaçao halted its ascent to avoid colliding with a U.S. Air Force refueling tanker on Friday, and the pilot blamed the military plane for crossing his path.

“We almost had a midair collision up here,” the JetBlue pilot said, according to a recording of his conversation with air traffic control. “They passed directly in our flight path. … They don’t have their transponder turned on, it’s outrageous.”

The incident involved JetBlue Flight 1112 from Curaçao, which is just off the coast of Venezuela, en route to New York City’s JFK airport. It comes as the U.S. military has stepped up its drug interdiction activities in the Caribbean and is also seeking to increase pressure on Venezuela’s government.

“We just had traffic pass directly in front of us within 5 miles of us — maybe 2 or 3 miles — but it was an air-to air-refueler from the United States Air Force and he was at our altitude,” the pilot said. “We had to stop our climb.” The pilot said the Air Force plane then headed into Venezuelan air space.

Derek Dombrowski, a spokesman for JetBlue, said Sunday: “We have reported this incident to federal authorities and will participate in any investigation.” He added, “Our crewmembers are trained on proper procedures for various flight situations, and we appreciate our crew for promptly reporting this situation to our leadership team.”

The Pentagon referred The Associated Press to the Air Force for comment. The Air Force didn’t immediately respond to a request for comment.

The Federal Aviation Administration last month issued a warning to U.S. aircraft urging them to “exercise caution” when in Venezuelan airspace, “due to the worsening security situation and heightened military activity in or around Venezuela.”

According to the air traffic recording, the controller responded to the pilot, “It has been outrageous with the unidentified aircraft within our air.”

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Trump admits he can’t tell if the GOP will keep the House despite massive investment pledges

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President Donald Trump admitted that he’s not sure if his economic policies will pay off for Republicans at the ballot box in 2026.

In an interview with the Wall Street Journal that was published late Saturday, he pointed to massive investment pledges that he’s secured since returning to the White House.

But when asked if Republicans will lose control of the House in next year’s midterm elections, Trump replied, “I can’t tell you. I don’t know when all of this money is going to kick in,” adding that forecasts say the second quarter.

Trump has previously touted as much as $21 trillion of investments pouring into the U.S., though recent commitments don’t come close to adding up to such levels.

Still, under trade deals Trump has negotiated, the European Union has vowed $600 billion in investment, Japan $550 billion, and South Korea $350 billion. Separately, Saudi Arabia has promised $1 trillion. Companies have also announced plans to invest hundreds of billions of dollars, though some of that includes money planned during the Biden administration.

While the timing of all the money is uncertain, not to mention how much will actually be spent, companies have expressed the need to diversify supply chains with more domestic production. Apple has said its $600 billion pledge to build U.S. factories will create a “domino effect” that ignites manufacturing across the country.

At the same time, Wall Street expects Trump’s tax cuts from his One Big Beautiful Bill Act to deliver a significant jolt of fiscal stimulus to the economy next year, potentially reaccelerating GDP growth.

That would come as voters made clear in last month’s off-year elections that affordability is their top priority. Inflation has cooled from its 2022 high, but prices are up sharply from pre-pandemic levels, and consumers are revolting over higher insurance, electricity and grocery bills. Even most Trump voters say the cost of living is bad.

Trump has dismissed the affordability issue as a Democratic “hoax” and insists prices are down. He told the Journal that he will lower prices.

“I think by the time we have to talk about the election, which is in another few months, I think our prices are in good shape,” Trump said.

“I’ve created the greatest economy in history. But it may take people a while to figure all these things out,” he added. “All this money that’s pouring into our country is building things right now—car plants, AI, lots of stuff. I cannot tell you how that’s going to equate to the voter, all I can do is do my job.”

Trump has floated some ideas to appease voters on affordability, including a 50-year mortgage to lower monthly payments and $2,000 “dividend” checks. He also continues to pressure the Federal Reserve to lower rates, even though it could worsen inflation, and rolled back tariffs on some food imports.

In his interview with the Journal, Trump didn’t say if he would cut tariffs on other goods. He also warned that if the Supreme Court strikes down his global tariffs, his alternatives are not as “nimble, not as quick.”

 “I can do other things, but it’s not as fast. It’s not as good for national security,” Trump added. 



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Nicotine pouches can be a better alternative to cigarettes says CEO

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Smoking is one of the clearest public-health failures of our time. More than 500,000 Americans still die each year from smoking-related illnesses, and globally the picture is even more alarming. In the United States, anti-smoking campaigns have reduced the number of new cigarette users, but the effectiveness of these measures may be fading. Indeed, the headline of a widely-shared news story notes “Celebrities Are Making Smoking Cigarettes Cool Again”. Yikes. Meanwhile, a quick trip to Mexico, Europe, or Asia is enough to see that cigarettes remain very much in style.

Reducing cigarette use, and preventing a new generation from getting hooked on nicotine, is a noble goal. That is one reason James Monsees and Adam Bowen founded the vape company JUUL Labs, as a potentially less harmful alternative for adult smokers. But a mix of regulatory missteps by a hostile FDA and market loopholes opened the door to a wave of counterfeit and bootleg vapes, often imported from China, sold in local stores, highly addictive, and completely unregulated. Many people became sick from using vapes with unknown ingredients. Teenagers were easily able to access bootleg vapes from China in youth-friendly flavors. What began as an idealistic goal—moving adult smokers off of cigarettes—turned into a new epidemic. 

Now we have two problems: cigarettes and vapes.

I believe science and technology can solve both. I was a tobacco user who became addicted to vaping. I tried everything to quit and cut down my nicotine use. Eventually, I discovered Swedish-style white pouches. That experience led me to create Sesh+, a premium, tobacco-free nicotine pouch made with transparent ingredients. It has been life-changing for me personally: I haven’t picked up a vape since switching to pouches. In Sweden, where oral nicotine products have been widely used for decades, smoking rates are among the lowest in Europe and smoking-related disease is correspondingly lower.

There is growing evidence that nicotine itself, while addictive, is not what primarily causes smoking-related disease; it’s the toxic byproducts of combustion that kill. With vaping, the concern is different: it’s the lack of transparency and quality standards that should alarm us. As a health-conscious consumer, I want to know exactly what I’m putting into my body. That’s why our pouches are independently lab-tested for contaminants like heavy metals and are manufactured in the United States under strict quality controls. 

Fake nicotine pouches are already in the U.S. market. Sofia Hamilton writes for Reason that her favorite convenience store unknowingly sells counterfeit nicotine pouches, and how only someone deeply familiar with FDA nicotine rules could tell the difference. No one should have to be a nicotine policy expert just to know whether a product is safe.

Important questions remain. We do not want to create a product that attracts people who don’t already use nicotine. The average Sesh+ customer is over 35, and I’m very proud of that. Early data is encouraging: a recent Rutgers study found that new nicotine users taking up pouches remains very low. Government has a responsibility to keep black-market and counterfeit pouches out of consumers’ hands. Industry must ensure retailers are educated and know what they’re selling. And we need strong youth prevention laws.

Nicotine pouches will only be effective if industry and government work together to ensure we are not attracting youth or non-nicotine users.

In the U.K., the proposed Tobacco and Vapes Bill would ban people born in or after 2009 from ever purchasing nicotine products. In the United States, we have already raised the legal age to buy tobacco to 21. These are the kinds of measures our industry should support. If the legislation in the U.K. passes, I hope other countries will adopt similar policies to prevent youth from accessing nicotine products. I also hope to see product-verification technology adopted as an industry standard so counterfeit nicotine products never reach consumers. Age verification is not enough; we must ensure a market for counterfeit and bootleg nicotine pouches does not emerge.

If companies in the nicotine pouch space work together, we can learn from JUUL’s experience and avoid repeating the same mistakes. Our responsibility is clear: help adult smokers move to potentially less harmful alternatives, without creating a new generation of nicotine users. If we get this right, a world free from tobacco is not just aspirational. It’s achievable.

Max Cunningham is the CEO of Sesh+, a nicotine pouch company based in Austin, Texas and backed by 8VC. The opinions expressed in Fortune.com commentary pieces are solely the views of their authors and do not necessarily reflect the opinions and beliefs of Fortune.



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