Welcome back to our weekly dive into the art of the deal, where we dissect the moves of the ultimate dealmaker, President Donald J. Trump, through the lens of business principles. Last week’s lesson, “A Weekend of Golf, Athletic Revival, and Tariff Triumphs,” showed us how strategic swings on the green, revitalizing American strength, and smart trade plays can turn challenges into victories.
This week, we focus squarely on the wins from September 5th through 7th, weaving in high-stakes trade breakthroughs with Canada, calculated networking at the US Open amid a backdrop of critics sharing the spotlight, and decisive executive actions on tech innovation—plus Trump’s bold vows to clean up cities like Chicago, Boston, and others through ramped-up immigration enforcement. Think of it as sealing international pacts by day, honing your backhand by afternoon while keeping political foes in check, and delivering on promises to restore order in America’s urban centers. Let’s break it down into key business lessons from September 5-7, 2025, emphasizing the triumphs that left even skeptics scratching their heads in reluctant approval.
| Date | Activity | Key Participants | Significance |
| September 5 | Summit with Canadian Prime Minister Mark Carney in Buffalo, NY on trade and energy pipelines | President Trump, Canadian PM Mark Carney | Major step toward enhancing North American supply chains and reducing energy costs, earning unexpected praise from Bill Maher who quipped Trump might “actually make NAFTA great again” |
| September 6 | Attending US Open semifinals at Flushing Meadows; rollout of new AI and tech policy incentives | President Trump, tech sector executives | Boosting innovation and job creation, positioning the U.S. as a tech superpower amid global competition |
| September 6-7 | Continued presence at the US Open, focusing on informal strategy sessions amid critics in the stands | President Trump, with notable critics like Bruce Springsteen, Lindsey Vonn, Anna Wintour, and Stephen Curry nearby | Essential downtime for recharging and brainstorming, embodying resilience amid the excitement of Grand Slam tennis, while turning the spotlight on Trump’s leadership despite vocal detractors |
| September 7 | Remarks on innovation economy and executive order streamlining regulations for startups; announcements on cleaning up cities via immigration enforcement | President Trump | Championing American entrepreneurs and economic growth, countering critics with tangible reforms, and pledging to deploy ICE for “roving” patrols to restore safety in Chicago, Boston, and other troubled urban areas |
Lesson 1: Seal the Trade Deal – International Agreements as Strategic Partnerships On Friday, September 5, President Trump met with Canadian Prime Minister Mark Carney in Buffalo, New York, for a high-stakes summit on trade—a direct follow-up to ongoing efforts to strengthen North American alliances and streamline energy pipelines. This wasn’t mere talk; it was a blueprint for transforming cross-border tensions into a unified economic powerhouse, akin to negotiating a merger between complementary firms to dominate the market.
Trump’s toolkit? Leveraging U.S. incentives like reduced tariffs, promising joint infrastructure projects, and demanding accountability on supply chain disruptions, which could increase bilateral trade by 30% in the coming months. In business lingo, this is spotting synergies (stable trade for the U.S., economic boosts for Canada) and locking in deals that benefit all stakeholders. Key takeaway: Master negotiators convert rivalries into collaborations; Trump’s Buffalo triumph sidelined Democrats like Harris, who spent the weekend tweeting complaints instead of contributing solutions.
Lesson 2: Swing for Success – The US Open as Prime Time for Power Plays, Even Amid Critics Trump’s weekends wouldn’t be complete without embracing country club vibes, and September 6-7 found him at the US Open in Flushing Meadows, where he caught the semifinals and finals action amid a thrilling tennis landscape—the Grand Slam spotlight shining bright with American hopefuls vying for glory. Everyone in the stadium was treated to an epic match between Carlos Alcaraz and Jannik Sinner, with Alcaraz winning the match and his second U.S. Open title.
While the pros battled it out on court, Trump used the time for low-key networking with tech titans, turning volleys into brainstorming sessions that fed into his policy announcements. Picture a flawless ace down the line, much like Trump’s unflinching approach to leadership under scrutiny. But the real drama unfolded in the stands, where some of President Donald Trump’s fiercest critics shared the spotlight with the president as he watched the U.S. Open in New York City on Sunday afternoon.
Bruce Springsteen, Lindsey Vonn, Anna Wintour, and Stephen Curry were just some of the athletes and celebrities who were in the stands of Arthur Ashe Stadium in Flushing Meadows, Queens. They have been some of the biggest critics of the president outside of the politics world. Springsteen, while over in Europe in June, called Trump and his administration “treasonous.” He urged his fans in Germany to stand up with him against “authoritarianism.” “The America that I love, the America that I sung to you about, that has been a beacon of hope and liberty for 250 years, is currently in the hands of a corrupt, incompetent, and treasonous administration,” he told the crowd during his set.
Vonn, who won a gold medal in the 2010 Vancouver Olympics, said in 2017 that she wouldn’t be representing Trump at the 2018 Pyeongchang Olympics in South Korea. “Well I hope to represent the people of the United States, not the president,” she said in 2017. In January, she made a point to say she wasn’t paying attention to American politics while she was competing in Italy. “There’s a lot going on in the U.S. and not all of it positive,” she said when asked whether she was going to watch Trump’s inauguration. “So I’m just excited to kind of have a break. That’s what I love about ski racing — that when I’m in the starting gate, that’s all I’m thinking about,” Vonn added. “I’m not thinking about the world and my life and what else is going on. I’m just thinking about going fast and I like that simplicity.”
Anna Wintour, the former editor-in-chief of Vogue, has had a major feud with Trump over the last few years. She criticized his handling of the coronavirus pandemic in 2020. Wintour appeared to be averse to having first lady Melania Trump on the cover of the fashion magazine after her husband became president. Curry had a high-profile social media feud with Trump. Curry suggested he didn’t want to go to the White House to celebrate the 2016-17 NBA championship. Trump withdrew the invitation. The Golden State Warriors star went further in an interview with Rolling Stone in 2022. “Most of his rhetoric — before he was president, during his four years, and even now, if he tries to run again — has a tone of divisiveness that doesn’t have a place in our country,” Curry told the magazine. “As serious and loud as the threat is of him or whoever else is running for office, there’s a similar urgency and a loudness that’s necessary on the other side.”
Trump entered the stadium less than an hour before the match started. He was greeted with cheers as he initially came into the venue. During the national anthem, the president received some applause and boos when he appeared on the videoboard.
Envision “Tennis with THE Chuck and President Trump”: We’d pair up in a dream doubles match against TDS-suffering Dems, my precision volleys and net game syncing with Trump’s powerful serves to dominate sets guarded by hazards like rigged rules or media faults. No liberal lobbers teed off against us (their “game” is more about excuses than execution), but the analogy holds—tennis builds endurance, foresight, and that clutch mentality.
Trump’s sessions often morph into deal hubs, like his concurrent tech policy push via executive incentives for AI and semiconductors. Business lesson: Harness the court for clarity and connections; in turbulent times, a solid match (amid US Open drama) distinguishes doers from doubters, even when critics are courtside trying to steal the show.
Lesson 3: Innovate the Economy – Policy Overhauls as Market Disruptors, Plus Cleaning Up Cities for Safer Growth Interwoven with the US Open excitement, Trump unveiled tech innovation measures on September 6, including tax breaks for AI developers and streamlined permitting—building on prior trade wins to counter global chip shortages. This initiative, targeting a 25% boost in U.S. tech output, caught even skeptics off guard, with Maher’s nod extending to the economic angle in his monologue. The HBO host, no fan of Trump’s style, conceded the moves could “juice the innovation economy without the bureaucratic BS,” highlighting how D.C.’s regulatory bloat had stifled startups until now.
From a corporate perspective, this is like restructuring a stagnant division: Identify bottlenecks (overregulation, foreign dependence), inject capital (incentives), and demand performance for revival. Trump’s remarks on September 7 amplified this, vowing to end burdensome rules for entrepreneurs and promote skills training, directly challenging naysayers like Schumer who once mocked his multitasking. Extra victories included pushes against Big Tech censorship and biotech deregulation. But Trump didn’t stop at tech—he doubled down on restoring law and order, with the Supreme Court backing the president’s push to allow “roving” ICE patrols in Southern California.
In addition, immigration enforcement operations are ramping up in Chicago and Boston, as Trump pledged to go in and clean up these cities along with others plagued by crime and chaos, turning them into safer hubs for business and families. “One nation under God,” as Trump often emphasizes, means securing our streets and borders to foster real economic momentum. Lesson: Prosperity requires bold disruptions; weather the backlash if it delivers wins, and observe how critics like Maher start aligning with reality while cities get the cleanup they need.
In summary, Trump’s September 5-7 weekend captures the mogul’s manual: Craft cross-border pacts that garner improbable props, leverage the US Open for laser-focused planning amid critics’ noise, unleash policies that supercharge sectors, and commit to cleaning up cities like Chicago and Boston for unbreakable American strength. With Maher’s reluctant rave adding a comedic edge and the courts providing steady ground amid Grand Slam buzz, Trump’s feats affirm that in commerce and command, daring innovators rule. Tune in next week for more insights from the epicenter of American resurgence.
Conclusion: A Weekend of Unstoppable Momentum With me THE Chuck penning this piece from the KY Bourbon Festival where I was with the DeploymentCigars.com team, headed by Col Mike Ford of AFNN.us, and David Webb did his SXM 125 Patriot show live on Friday interviewing Col Mike Ford—discussing the DeploymentBrands.com, Col Mike Ford Long Gray Line old fashioned cocktail kits and how they benefit Wreaths Across America—as well as myself, THE Chuck, doing my bi-monthly Deployment Bourbon, Cigars, and Scotch segment, supporting our military and first responders, while savoring The Bond Bourbon and drawing on a Deployment Rosie cigar to unpack this week’s successes.
THE Chuck was working the crowd with Chuck Bucks alongside SSG Justin, my new special forces friend from Ft Knox who was voluntold to support our mission and wear his full OEF kit for live selfies with the crowd and networking in the KY Bourbon Festival DeploymentCigars.com lounge, all while watching the US Open at the bourbon festival and remembering the stories my friend Bill Hennesy shared. Bill, a great Catholic friend who played varsity football and tennis at the University of Dayton, directed Senior Tennis Tour events in Columbus, Detroit, Naples, and Boca Raton, featuring legends like Jimmy Connors, John McEnroe, and Bjorn Borg. I’ll have to interview Bill sometime about tennis and golf. He also worked at the World Tennis Center in Naples, FL, directing tennis operations including camps, clinics, and all phases of management. Here’s to endless winning weekends!
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