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Joseph B. Darby III

Jay focuses his practice on business and transactional tax law. He advises a wide variety of corporations and high-net-worth individuals on tax and legal aspects of business and real estate activities and represents these taxpayers before federal and state taxing authorities. He also works with high-net-worth individuals and business owners to organize their personal income tax and estate planning affairs in order to maximize wealth preservation and minimize tax on transfers to family members, charities and other recipients. This is accomplished through the use of the latest sophisticated estate planning strategies, including family limited partnerships, installment sales to defective grantor trusts, the formation of family charitable foundations, and other similar techniques. Jay was one of the early proponents of Opportunity Zones, and has been at the leading edge of the legislation and related tax incentives since they were first enacted in the Tax Cuts and Jobs Act in late 2017. He has spoken at over a dozen National conferences on the structuring of Qualified Opportunity Funds and Qualified Opportunity Zone businesses, and has helped form more than a dozen successful Qualified Opportunity Funds thus far, ranging in size from small private transactions to transactions in the $200 million to $500 million range.

Recent Posts

Legends of the Fall

Posted by Joseph B. Darby III on Oct 31, 2018 9:12:53 AM

When the Red Sox clinched the 2018 World Series last Sunday night, the first emotion was one of intense relief – relief that this wonderfully dynamic and exciting team actually managed to run the table and win an all-too-elusive championship. 

As I discussed the next morning with my partner and fellow baseball fanatic, Rich Jones, it is extremely common for great baseball teams to stumble before crossing the finish line. The Boston Red Sox teams of 1975 and 1986, for example, had similarly talented teams that enjoyed similarly jubilant seasons, only to come up oh-so-short in the seventh game of each World Series. Quadruple that comment for the 1967 Red Sox: The "Impossible Dream" team kept the Dream alive until the last out of the seventh game of the World Series. So close and yet so painfully far. The gods of baseball are indeed fickle.

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Topics: Boston Red Sox

Halfway Home

Posted by Joseph B. Darby III on Oct 26, 2018 4:52:17 PM

The Boston Red Sox are “halfway home” to a World Series Championship, having jumped to a 2-0 lead in games over the Los Angeles Dodgers, which, paradoxically, means that they are now “on the road” for three games in Los Angeles.

The Red Sox have been an amazingly successful road team during these 2018 playoffs, taking two-in-a-row at Yankee Stadium, followed by three-in-a-row in Houston – all played against the two best teams (other than the Red Sox) in baseball this season. Pretty darned impressive so far!

At the moment, there is a confident – and perhaps over-confident – sense that the last baseball game of the season has been played at Fenway Park, and that the Red Sox will win at least two of three games at Dodger Stadium in Los Angeles and jubilantly close out one of the most successful seasons in Major League Baseball history.

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Topics: Boston Red Sox, Boston Sports, World Series

Red Sox Mania: A World (Series) of Worry

Posted by Joseph B. Darby III on Oct 23, 2018 3:03:11 PM

The Boston Red Sox, as everyone in New England surely knows by now, are back in the World Series for the 4th time in 15 years. 

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Topics: Boston Sports, World Series

Red Sox on the Cusp

Posted by Joseph B. Darby III on Oct 19, 2018 8:50:57 AM

My buddy Darren from Australia is a die-hard sports fan who loves rugby, soccer, Australian rules football, and all the other interesting and slightly violent sports that are so popular Down Under. Since moving to the U.S., Darren has even developed an affinity for baseball, although he is not entirely sure of the rules.

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Topics: Boston Red Sox, World Series

How to Pay for College: Tax Savvy Tips for Parents

Posted by Joseph B. Darby III on Oct 16, 2018 3:50:11 PM

Once upon a time, a college degree was a true bargain: Four years of tuition cost about the same amount as a fancy new automobile, and pretty much set you up for life. Today, the price of that same college degree has sky-rocketed: The full-in cost of a college degree is now closer to the cost of a new house, and the size of the student loan has grown from a car loan to a mortgage. Every parent still wants to send a child to college, but the affordability factor is daunting and getting worse. Fortunately, there are smart, savvy ways to manage the looming costs of college – but they are not necessarily intuitive or easy to identify.

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Topics: Saving for College, Tax Planning

Last Call for the OVDP Program!

Posted by Joseph B. Darby III on Apr 19, 2018 12:50:58 PM

The IRS has announced that the Overseas Voluntary Disclosure Program (OVDP), which has been around since March 2009, is about to be shut down permanently, effective September 28, 2018.

The OVDP Program has seen over 56,000 taxpayers come forward voluntarily, paying over $11 billion in back taxes interest and penalties. The Program has always been a great deal for people who actually hid assets offshore, failed to report taxable income, and then want to come clean and get back into compliance, especially because the IRS is hot on everybody’s trail thanks to the FATCA regime and other enhanced offshore investigative techniques.

The IRS wants to terminate the Program because participation has declined steadily, from a peak of 18,000 disclosures in 2011, to only about 600 disclosures in 2017. However, the IRS is expected to maintain its aggressive posture on offshore tax avoidance, and so now is the last clear chance for people to take advantage of the OVDP Program and avoid severe sanctions (including criminal prosecution) for dubious past conduct.

Don’t miss this last call to help taxpayers come into compliance under this de facto “amnesty” program that ends on September 28, 2018. Call us at (617) 338-2985 if you or a client would like our assistance in “coming in from the cold” under the Program.

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Topics: IRS, Taxes, OVDP, offshore

Important Documents to Review Before Diving in to Trump's Tax Plan

Posted by Joseph B. Darby III on Dec 20, 2017 5:00:56 PM

Below are links to two documents that review some of the changes implemented by Trump's new tax plan. 

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Topics: GOP, Tax Plan, Trump Tax Reform

Chemistry Lesson: What Our Red Sox REALLY Need is Law and Order and a Good Judge (Not Aaron) in the Clubhouse

Posted by Joseph B. Darby III on Aug 28, 2017 9:41:53 AM

As the Boston Red Sox head into the home stretch of this 2017 baseball season, we Red Sox fans – a naturally dour and fretful bunch – worry whether this team is built for success in the upcoming MLB playoffs. After all, a very similar team – to wit, the not-ready-for-prime-time 2016 Red Sox – appeared on the October stage and proceeded to stink out the joint, getting swept 3-0 by the Cleveland Indians while delivering the worst group performance since the movie Waterworld was released. For sheer group ineptitude, the only comparable recent event was watching the Republican Senate try to fix Obamacare. Yeesh.

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Topics: Sports, Boston Red Sox, Don Baylor

The Tall Tax Tale of Why Country Songwriters Get Capital Gain Treatment

Posted by Joseph B. Darby III on Aug 18, 2017 1:41:21 PM

As a tax lawyer, my professional life has the elements that my grandfather believed were essential to a really good job: indoor work, no heavy lifting.

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Topics: The Eisenhower Rule, Code Section 1221, tax break, capital gains

The Gift That Keeps on Giving - To the IRS

Posted by Joseph B. Darby III on Mar 17, 2017 7:48:35 AM

GettyImages-508893778.jpgA rather stunning near–catastrophe almost occurred in the art world recently, and only dumb luck – namely, a casual off-hand remark with a savvy tax adviser  saved the art owner from a huge, self-inflicted tax bill from the Internal Revenue Service. A non-U.S. taxpayer (meaning a non-resident alien in tax parlance) had an extremely valuable painting being displayed in a U.S. museum or gallery and, for a variety of reasons, he wanted to transfer the painting to his spouse, who is also a non-resident alien. Let’s assume for the sake of argument that the painting was worth $50 million. Because the gift was from a non-resident alien to his non-citizen spouse, and the property was tangible property located or situated within the United States at the time of the transfer, this transfer would have been subject to tax the U.S. gift tax regime, at a tax rate of up to 40%. WHAAAAATTTTT???!!!

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Topics: estate tax, IRS, Tax, transfer tax

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About the Blog


Sullivan's Tax & Sports Update provides timely updates and cutting-edge commentary on all issues affecting U.S. taxation, and, of course, an always humorous take on sports! Edited by Joseph B. Darby III, a partner in Sullivan's Tax Department.

The material on this site is for general information only and is not legal advice. No liability is accepted for any loss or damage which may result from reliance on it. Always consult a qualified lawyer about a specific legal problem.

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