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   Brew Review // Morning Brew // Update
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     A kaleidoscopic look at one of life’s certainties...
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             February 08, 2026
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                 Jay Daniel Wright
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           <h3 style="color:#1c7ff2;margin-top:0;margin-bottom:0;font-family:Helvetica,Arial,sans-serif;font-size:16px;font-weight:700">
            EDITOR’S NOTE
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                  Good morning.
                 </strong>
                 The NFL season comes to a close today with Super Bowl LX, but another equally exciting season is already upon us: tax season. In fact, the two seasons have more in common than you might think: They both have hikes, cuts, and game-changing returns. Today, we’re even diving into post routes, cheating, hustling on the sidelines, and free agency (all in a tax context, of course). So, read on, and make sure to let the IRS know if you hit that parlay tonight.
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            GOVERNMENT
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                 If you file your taxes on time, that might be too late
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                 Unlike soup, tax returns are not always better a day later, which is why we’ve got some devastating news for procrastinators: Filing your tax returns via mail on April 15 may not get the job done anymore. Due to some changes at the US Postal Service, mail might not be postmarked on the same day it’s sent out, turning that 11th-hour success story into an April 16 dud.
                </p>
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                 <strong style="color:#000">
                  What’s changing?
                 </strong>
                 Technically, the USPS isn’t changing how it postmarks things. It’s still going to stamp the day’s date on your letter or package when it gets to a processing facility. But your mail might take longer to actually make it to that facility.
                </p>
                <p style="margin-top:0;margin-bottom:15px;line-height:22px">
                 That’s in part because the USPS is trying to save money by cutting back on how often it picks up mail from local post offices, making same-day postmarking less common, the agency
                 <a class="link" style="color:#333;border-bottom:2px solid #1c7ff2;text-decoration:none" target="_blank">
                  warned
                 </a>
                 at the end of last year. But there are a few alternative options:
                </p>
                <ul style="margin-top:0;padding-left:30px">
                 <li style="margin-bottom:10px;line-height:22px">
                  <span>
                   Ask someone at the post office to manually postmark your tax return.
                  </span>
                 </li>
                 <li style="margin-bottom:10px;line-height:22px">
                  <span>
                   Deliver tax documents via UPS or FedEx.
                  </span>
                 </li>
                 <li style="margin-bottom:10px;line-height:22px">
                  <span>
                   File taxes electronically.
                  </span>
                 </li>
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                <p style="margin-top:0;margin-bottom:15px;line-height:22px">
                 <strong style="color:#000">
                  Beyond taxes:
                 </strong>
                 Post-deadline postmarks aren’t just a potential tax problem. All time-sensitive mail, like bills and ballots, could be affected, so set your calendar reminders accordingly.—
                 <em>
                  BC
                 </em>
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            Presented By Northwestern Mutual
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              Get more from your tax return
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             <p style="margin-top:0;margin-bottom:15px;line-height:22px">
              You can’t control how much you owe in taxes, but you
              <em>
               can
              </em>
              control
              <a class="link" style="color:#333;border-bottom:2px solid #1c7ff2;text-decoration:none" target="_blank">
               how you prepare
              </a>
              . And the more you know about tax regulations that impact you, the better you’ll be able to plan. That’s where
              <a class="link" style="color:#333;border-bottom:2px solid #1c7ff2;text-decoration:none" target="_blank">
               Northwestern Mutual
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              comes in.
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             <p style="margin-top:0;margin-bottom:15px;line-height:22px">
              Northwestern Mutual’s financial advisors can help you understand which tax laws apply to you and uncover blind spots and opportunities you may not have otherwise thought of.
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             </p>
             <p style="margin-top:0;margin-bottom:15px;line-height:22px">
              From tax-advantaged savings tools to understanding which deductions are right for you, your financial advisor will help build a plan that helps you minimize your tax impact and maximize your savings—so you can hang onto your hard-earned money and put it where it matters.
             </p>
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              <a class="link" style="color:#333;border-bottom:2px solid #1c7ff2;text-decoration:none" target="_blank">
               Here’s how it works
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              .
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            FINANCE
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                <a style="color:#000;border-bottom:none;text-decoration:none" target="_blank">
                 Do local tax hikes actually scare off millionaires?
                </a>
               </h1>
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               <span class="source" style="margin-top:5px;margin-bottom:0;padding-left:10px;line-height:14px;display:inline-block">
                <small>
                 <em>
                  Alyssa Nassner
                 </em>
                </small>
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                 The folks streaming the Super Bowl from their couches sometimes cheer the idea of hiking taxes on those privileged to watch it from the stadium’s executive box. But high-earners and some critics claim that local tax hikes can backfire, since those jetting into Santa Clara, CA, for the big game today could also pack their bags for good in a move to lower-tax jurisdictions.
                </p>
                <p style="margin-top:0;margin-bottom:15px;line-height:22px">
                 The debate is gaining steam in 2026, as several states and cities consider reaching into the deepest local pockets to cover public spending:
                </p>
                <ul style="margin-top:0;padding-left:30px">
                 <li style="margin-bottom:10px;line-height:22px">
                  <span>
                   New York Mayor Zohran Mamdani is lobbying state leaders to raise taxes on the richest New Yorkers to fund campaign proposals like free childcare and bus service.
                  </span>
                 </li>
                 <li style="margin-bottom:10px;line-height:22px">
                  <span>
                   Several state legislatures, including Virginia’s, Washington’s, and Rhode Island’s, are mulling their own millionaire income tax hikes, while Californians might soon vote on a ballot measure that would impose a one-time 5% tax on the wealth of residents worth $1 billion or more.
                  </span>
                 </li>
                </ul>
                <p style="margin-top:0;margin-bottom:15px;line-height:22px">
                 Some wealthy New Yorkers have threatened to leave the Big Apple over taxes. And Google co-founder Larry Page already left California in response to the state’s proposed billionaire tax. Venture capitalist David Sacks personally left California for Austin, TX. His firm, Craft Ventures, opened an office in Austin but is maintaining its San Francisco location too. Other Silicon Valley billionaires, like Nvidia CEO Jensen Huang, said they won’t ditch the Bear State.
                </p>
                <h2 style="color:#000;margin:0 0 15px;font-family:Helvetica,Arial,sans-serif;font-size:19px;font-weight:700">
                 Moneybags repellent?
                </h2>
                <p style="margin-top:0;margin-bottom:15px;line-height:22px">
                 The millionaire tax in Massachusetts, which slaps a 4% surcharge on income over $1 million, passed in 2022 and has been held up as a success story. Supporters laud the levy for bringing in almost $6 billion to the state’s coffers over the first two years, boosting education funding and plugging gaps in the public transit budget.
                </p>
                <p style="margin-top:0;margin-bottom:15px;line-height:22px">
                 Boosters claim that wealthy Massachusetts residents
                 <a class="link" style="color:#333;border-bottom:2px solid #1c7ff2;text-decoration:none" target="_blank">
                  haven’t rushed to rent U-Hauls
                 </a>
                 , citing the rising number of millionaires in the state since the tax was imposed, perhaps because the state’s high quality of life outweighs the tax burden. But the Boston-based libertarian think tank Pioneer Institute
                 <a class="link" style="color:#333;border-bottom:2px solid #1c7ff2;text-decoration:none" target="_blank">
                  insists
                 </a>
                 that local wealth growth is largely due to ballooning asset values and notes that counting Mass-based millionaires doesn’t reflect the number of affluent residents moving to lower-tax destinations like Florida and New Hampshire.
                </p>
                <p style="margin-top:0;margin-bottom:15px;line-height:22px">
                 <strong style="color:#000">
                  Big picture:
                 </strong>
                 Evidence from across the US is mixed, as several
                 <a class="link" style="color:#333;border-bottom:2px solid #1c7ff2;text-decoration:none" target="_blank">
                  studies
                 </a>
                 <a class="link" style="color:#333;border-bottom:2px solid #1c7ff2;text-decoration:none" target="_blank">
                  show
                 </a>
                 that millionaires don’t move en masse in response to tax hikes, and when they do, it’s not as significant as headlines might imply. Though
                 <a class="link" style="color:#333;border-bottom:2px solid #1c7ff2;text-decoration:none" target="_blank">
                  some
                 </a>
                 <a class="link" style="color:#333;border-bottom:2px solid #1c7ff2;text-decoration:none" target="_blank">
                  research
                 </a>
                 pushes back, saying that a not-insignificant number of high earners do leave over time.
                 <em>
                  —SK
                 </em>
                </p>
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            SPORTS
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                 For some athletes, winning means no state taxes
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                 Professional athletes have an incentive to play in US states like Florida and Tennessee, and it’s not for the proximity to Disney World or Dollywood. They are among the states without income taxes—meaning those huge contracts are worth even more there than in other states.
                </p>
                <p style="margin-top:0;margin-bottom:15px;line-height:22px">
                 <strong style="color:#000">
                  For example:
                 </strong>
                 Mikko Rantanen spent the first 10 years of a very successful NHL career with the Colorado Avalanche and enjoyed the state’s flat 4.4% income tax rate. In January 2025, he was traded to the (North) Carolina Hurricanes, which had a similar flat tax rate of 4.25%. Three months later, he was traded again, this time to the Dallas Stars, where he immediately signed an eight-year, $96 million extension to play in the income tax-free land of Texas, after turning down similar offers from his previous two employers.
                </p>
                <p style="margin-top:0;margin-bottom:15px;line-height:22px">
                 While Rantanen never publicly cited the extra ~$4 million he will make over the life of the deal by playing in Texas instead of Colorado or North Carolina as a motivator, other players have vocalized the draw of states without income taxes:
                </p>
                <ul style="margin-top:0;padding-left:30px">
                 <li style="margin-bottom:10px;line-height:22px">
                  <span>
                   NBA player Grant Williams left Boston and signed a $54 million contract with Dallas in 2023. Not only does Massachusetts have a 5% state tax, but the state also passed a law in 2022 that adds a 4% surtax on income above $1 million. “In Boston, it’s really like $48 million with the millionaire’s tax, so $54 million in Dallas is really like $58 million in Boston,” Williams
                  </span>
                  <span>
                   <a class="link" style="color:#333;border-bottom:2px solid #1c7ff2;text-decoration:none" target="_blank">
                    said
                   </a>
                  </span>
                  <span>
                   .
                  </span>
                 </li>
                 <li style="margin-bottom:10px;line-height:22px">
                  <span>
                   NFL player Tyreek Hill chose to sign with the Dolphins in Miami, Florida, over the New York Jets (who play in New Jersey) in free agency. While no one would ever question why someone wouldn’t want to play for the Jets, when asked why he made that decision, Hill
                  </span>
                  <span>
                   <a class="link" style="color:#333;border-bottom:2px solid #1c7ff2;text-decoration:none" target="_blank">
                    said
                   </a>
                  </span>
                  <span>
                   , “Those state taxes, man.” By living in Florida instead of New Jersey, he saved $9 million in income taxes over the course of his three-year, $90 million contract.
                  </span>
                 </li>
                </ul>
                <p style="margin-top:0;margin-bottom:15px;line-height:22px">
                 <strong style="color:#000">
                  Individual athletes consider taxes, too.
                 </strong>
                 Unlike in team sports, pro golfers and tennis players can call anywhere home. Many choose Florida, Texas, and Nevada due to the friendly tax laws (and the warm weather).
                </p>
                <p style="margin-top:0;margin-bottom:15px;line-height:22px">
                 <strong style="color:#000">
                  Colleges can do the same:
                 </strong>
                 Last year, Arkansas became the
                 <a class="link" style="color:#333;border-bottom:2px solid #1c7ff2;text-decoration:none" target="_blank">
                  first state
                 </a>
                 to make the name, image, and likeness (NIL) money that athletes receive tax exempt. Five other states—Georgia, Illinois, Louisiana, New Jersey, and South Carolina—are considering similar measures.
                </p>
                <p style="margin-top:0;margin-bottom:15px;line-height:22px">
                 <strong style="color:#000">
                  More to come?
                 </strong>
                 Several states, including Mississippi, Kentucky, and Missouri, are working to
                 <a class="link" style="color:#333;border-bottom:2px solid #1c7ff2;text-decoration:none" target="_blank">
                  reduce or eliminate
                 </a>
                 income taxes. They are each home to SEC schools, and likely feeling pressure to compete with Big Ten football programs.
                 <em>
                  —DL
                 </em>
                </p>
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            Together With Northwestern Mutual
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               Tax season starts now.
              </strong>
              Everyone wants to know
              <a class="link" style="color:#333;border-bottom:2px solid #1c7ff2;text-decoration:none" target="_blank">
               how to get a bigger tax refund
              </a>
              . And while you can’t control how much you owe, you can control how you prepare. Learn how
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               Northwestern Mutual financial advisors
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              can help you create
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               a financial plan to meet your goals
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              .
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            FIRST-PERSON POV
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                <a style="color:#000;border-bottom:none;text-decoration:none" target="_blank">
                 How I did my side hustle taxes
                </a>
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               <img alt="On stage performance with giant blonde wig" src="https://inboxflows.com/_/image/https%253A%252F%252Fmorningbrew.com%252Fcdn-cgi%252Fimage%252Fwidth%253D1240%252Cformat%253Dauto%252Fhttps%253A%252F%252Fstorage.morningbrew.com%252Fimage%252F2026-02-04%252Fimage-ebbec9873a1645b217b0b1596b7c403b61bc8e6b-7008x4672-jpg%252FKillTime-16.jpg/?inbox_flows_img_sig=eyJwYXRoIjoiaHR0cHMlM0ElMkYlMkZtb3JuaW5nYnJldyIsInRpbWUiOjE3NzA1NDg4NzUuMjE4NjgyM30:1vp2dv:xmFQId3pnXxpi_42tU85MB8IS8kAAVYiQPykPw2TNjo" style="width:100%;max-width:670px;display:block" width="670"/>
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                 <em>
                  Matty Merritt, live on stage. Aaron Klinger
                 </em>
                </small>
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                <p style="margin-top:0;margin-bottom:15px;line-height:22px">
                 You would be disgusted by how much I spent on wigs last year. I run a small theater company in Chicago called Dinner Cut. Last year, I started taking my shows and projects seriously as a business, and officially
                 <a class="link" style="color:#333;border-bottom:2px solid #1c7ff2;text-decoration:none" target="_blank">
                  formed an LLC
                 </a>
                 . This is not official tax advice, but anecdotally, here’s how I prepared my tax return for the first year of my very niche small business.
                </p>
                <h2 style="color:#000;margin:0 0 15px;font-family:Helvetica,Arial,sans-serif;font-size:19px;font-weight:700">
                 From Google Sheet to Schedule C
                </h2>
                <p style="margin-top:0;margin-bottom:15px;line-height:22px">
                 I have a single-member LLC which, for tax purposes, doesn’t exist separately from me, its owner. So, Dinner Cut’s income—like the
                 <a class="link" style="color:#333;border-bottom:2px solid #1c7ff2;text-decoration:none" target="_blank">
                  $10,100 grant
                 </a>
                 it received from the state of Illinois—and expenses get reported on a Schedule C form on my personal tax return. And this leads to the first point of tax preparation that I am passionate about.
                </p>
                <p style="margin-top:0;margin-bottom:15px;line-height:22px">
                 If you’re just starting to think about your 2025 side hustle taxes—and I say this with all the love in my heart—you are too late. The most important part about doing taxes for a teeny-tiny business is tracking every single dollar spent throughout the year, so, come tax time, you are clear-eyed enough to maximize your refund (or, at least, organized enough to make sure you don’t end up with a huge tax bill). I’m sure there are tons of budget-tracking apps and software, but I love a simple
                 <a class="link" style="color:#333;border-bottom:2px solid #1c7ff2;text-decoration:none" target="_blank">
                  Google Sheet
                 </a>
                 , because it forces me to face every expense, even if (no, especially if) it is more sequined fabric that I don’t need.
                </p>
                <p style="margin-top:0;margin-bottom:15px;line-height:22px">
                 <strong style="color:#000">
                  Hot tip:
                 </strong>
                 I group most of my expenses by project, but straight-up telling the IRS that I spent $11,255 on a stage adaptation of
                 <em>
                  The Lizzie McGuire Movie
                 </em>
                 wouldn’t work because…they have no idea what that is.
                </p>
                <p style="margin-top:0;margin-bottom:15px;line-height:22px">
                 So, to make tax time easier, my budget-tracking sheet has two columns for descriptions: The first one is named in a way that makes sense to my brain. The second one is for traditional tax categories like “Small Tools and Equipment” (hot glue gun) or “Space Rental” (dance studio rental) that belong on the Schedule C. And the person who helps categorize them is my incredible tax lady/jewelry artist, Janet, who specializes in independent artists’ taxes. As soon as you start getting more than two forms come tax time, I truly believe it’s worth it to find a real, qualified human to help you.
                </p>
                <p style="margin-top:0;margin-bottom:15px;line-height:22px">
                 <strong style="color:#000">
                  What to write off.
                 </strong>
                 You can write off a lot more than you think, including part of your rent or mortgage if you use your home for your business, some of your cellphone or internet bill, mileage, and business travel. I recommend getting your own tax lady to help you through it, or if you’re an artist, taking this
                 <a class="link" style="color:#333;border-bottom:2px solid #1c7ff2;text-decoration:none" target="_blank">
                  workshop
                 </a>
                 taught by my tax lady.
                 <em>
                  —MM
                 </em>
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            CULTURE
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                 Tax scandals you may have forgotten about
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                  Mark Perlstein/Getty Images
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                <p style="margin-top:0;margin-bottom:15px;line-height:22px">
                 Reality TV stars, athletes, and Shakira are not the only rich or famous people who have gotten into trouble with the taxman. Here are four “did you know?”-worthy accounting dramas, ranging from oopsie to big-time crime:
                </p>
                <p style="margin-top:0;margin-bottom:15px;line-height:22px">
                 <strong style="color:#000">
                  Willie Nelson:
                 </strong>
                 In 1990, tax collectors seized the assets of America’s favorite bandana-wearing country singer after finding that he owed $16.7 million. Nelson sued his accountants for mishandling his money, settling for an undisclosed sum that didn’t cover his debt. To repay it, he
                 <a class="link" style="color:#333;border-bottom:2px solid #1c7ff2;text-decoration:none" target="_blank">
                  released
                 </a>
                 a 25-song collection called
                 <em>
                  The IRS Tapes: Who’ll Buy My Memories?
                 </em>
                 with all proceeds going to the agency. The album raised $3.6 million, and Nelson later paid off the rest.
                </p>
                <p style="margin-top:0;margin-bottom:15px;line-height:22px">
                 <strong style="color:#000">
                  Floyd Mayweather Jr.:
                 </strong>
                 The legendary boxer is undefeated inside the ring, but he’s been knocked out by an audit. Mayweather paid $22.2 million in back taxes in 2017 and another $5.5 million in 2023. Fortunately, the first, larger
                 <a class="link" style="color:#333;border-bottom:2px solid #1c7ff2;text-decoration:none" target="_blank">
                  repayment
                 </a>
                 came due around the time that Mayweather boxed Conor McGregor in a match that guaranteed him $100 million.
                </p>
                <p style="margin-top:0;margin-bottom:15px;line-height:22px">
                 <strong style="color:#000">
                  Al Capone:
                 </strong>
                 The accounting industry is probably still chasing the high of 1931. That year, federal officials
                 <a class="link" style="color:#333;border-bottom:2px solid #1c7ff2;text-decoration:none" target="_blank">
                  indicted
                 </a>
                 notorious gangster Al Capone for tax evasion—the first major charge they got to stick to him—after a team that included an undercover IRS agent found unreported gambling income. His conviction landed him in prison for seven years, mostly spent at Alcatraz.
                </p>
                <p style="margin-top:0;margin-bottom:15px;line-height:22px">
                 <strong style="color:#000">
                  Robert Brockman:
                 </strong>
                 The US government referred to its 2020 fraud indictment of Brockman, the late automotive software CEO, as its largest-ever tax evasion case against an individual. He was awaiting trial and on the hook for $1.4 billion in back taxes, penalties, and interest when he died in 2022. In December, his estate agreed to
                 <a class="link" style="color:#333;border-bottom:2px solid #1c7ff2;text-decoration:none" target="_blank">
                  settle
                 </a>
                 up for $750 million.
                 <em>
                  —ML
                 </em>
                </p>
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            BREW'S BEST
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                 <p style="margin-top:0;margin-bottom:15px;line-height:22px">
                  <img alt="" src="https://inboxflows.com/_/image/https%253A%252F%252Fem-content.zobj.net%252Fthumbs%252F120%252Fapple%252F237%252Fwhite-heavy-check-mark_2705.png/?inbox_flows_img_sig=eyJwYXRoIjoiaHR0cHMlM0ElMkYlMkZlbS1jb250ZW50LiIsInRpbWUiOjE3NzA1NDg4NzUuMjE5NTkwNH0:1vp2dv:coFvMh9NTb86chI9Fht-sCJo8A5W5QYFsG7hpXqjYhg" style="max-width:18px" width="18"/>
                  <strong style="color:#000">
                   Save:
                  </strong>
                  All that tax return money has to go somewhere. Why not
                  <a class="link" style="color:#333;border-bottom:2px solid #1c7ff2;text-decoration:none" target="_blank">
                   this wallet
                  </a>
                  ?**
                 </p>
                 <p style="margin-top:0;margin-bottom:15px;line-height:22px">
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                  .
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                  Tax preparation
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