On April 16, 2025, the U.S. Tax Court ruled (Decision) against hedge fund manager GWA LLC (GWA) in its challenge of an IRS judgment finding that basket options it had purchased from Royal Bank of Canada (RBC) and Deutsche Bank were taxable on an annual basis and that GWA was, for tax purposes, the owner of the basket securities. GWA, which filed for bankruptcy in April 2024, had made large profits by trading on the securities. It had unsuccessfully argued before the IRS that those profits were long-term capital gains, and hence it was appropriate to defer taxes on them at least until the exercise or termination of the options. The Tax Court rejected that argument, along with the manager’s claims to have relied on legal counsel regarding its trading activities.
Given how common it is for hedge funds to use leverage, and to make use of basket option contracts, the ruling against GWA has implications for the private funds space and the direction of tax policy and enforcement. This article presents a summary of the Decision as well as analysis from legal experts.
See “Hedge Funds Are Required to Disclose Basket Option Contracts and Basket Contracts” (Aug. 6, 2015).
Relevant Entities and Activities
GWA, which operated as GWA LLC and Weiss Multi-Strategy Advisers LLC (WMSA), began in 1978 as Weiss Associates under the leadership of founder George Weiss, with a focus on securities trading and brokerage, the Decision relates. In 1986, Weiss began to offer investors an opportunity to invest in a hedge fund, framing the pitch in terms of a “relative value long/short strategy,” according to the Tax Court. That strategy involved buying and selling stocks from a given industry in approximately equal dollar amounts.
The hedge fund grew rapidly and, by the middle of the 1990s, had $1.7 billion in assets under management (AUM). Riding on that success, Weiss and his colleagues began to invest their own money in the hedge fund, and, in 1996, Weiss registered it as GWA LLC. Using a selective process with high income thresholds, he offered key employees of Weiss Associates a stake in GWA, but total membership in the vehicle never exceeded 50, according to the Decision.
GWA made use of the common “2 and 20” compensation model, whereby its principal took home profits consisting of two percent of AUM and 20 percent of annual gains. In the view of the Tax Court, the fairly conservative long-short investment strategy that Weiss put to use brought in relatively small, although consistent, gains over time, prompting the manager to turn to leverage in the hope of building exposure and returns. As part of this strategy, GWA made extensive use of affiliates, including:
- George Weiss & Co. LLC, in which GWA held a controlling interest in 1997 and 1998; and
- OGI Associates LLC (OGI), which was launched in 1994 to use GWA’s proprietary capital to trade securities. According to the Decision, GWA was OGI’s sole member and Weiss its only manager as of May 28, 1998.
The Role of OGI
As a single-member limited liability company under GWA’s ownership, OGI sought not to be classified as a corporation and to be disregarded as an entity separate from its owner. Hence, under Treasury Regulation 301.7701‑2, OGI’s activities would be “treated in the same manner as a sole proprietorship, branch, or division of the owner,” the Decision explains.
OGI and Weiss Associates made an investment banking services agreement in 1998 giving the latter the right to “perform investment operations and investment banking functions” for OGI, the Tax Court alleged. With this arrangement in place, GWA pursued a strategy making extensive use of specially tailored financial instruments (SFTIs), ultimately investing hundreds of millions of dollars in what it judged to be “call options” with the RBC and then with Deutsche Bank.
According to the Decision, the call options had expiration dates ranging from five years to as long as 12 years in the future, and their underlying asset was a basket holding hundreds or thousands of different stocks, potentially varying from one hour to the next. Although, in theory, the bank was the owner of the basket, GWA was able to make trades using the securities as it pleased and relying on the long/short strategies that were its modus operandi.
GWA traded heavily in RBC and Deutsche Bank basket options, generating very high profits, cross-trading extensively with OGI and then attempting to escape tax consequences by passing off OGI as the entity that had made mark-to-market elections. In terms of profitability, the strategy worked out well for GWA, enabling it to make significant gains on the trades of securities that the baskets held, while retaining the choice of not exercising the option on the securities until maturity and thus deferring taxation on the trading profits for the foreseeable future. If and when taxes were finally levied, they would be long-term, capital gains taxes and thus less than taxes on trading profits.
In the Tax Court’s view, OGI operated effectively as little more than a shell company or a front designed to deflect tax liability from GWA. “Because OGI’s securities trading activities are regarded as being conducted by GWA, OGI cannot be regarded as the ‘trader in securities’ for purposes of section 475(f)(1),” states the Decision.
See “FRA Program Analyzes the Tax Implications of Common Hedge Fund Investment Strategies” (Aug. 5, 2021).
Relations With Deutsche Bank
When GWA’s first three RBC contracts were set to expire in six months, Weiss’s associate Frederick Doucette undertook negotiations with Deutsche Bank, which offered more competitive terms than those of the GWA-RBC arrangement. According to the Decision, RBC charged a financing fee on 100 percent of the investment capital funneled through the prime brokerage account. In contrast, Deutsche Bank applied such a fee only on the portion of capital invested in the reference basket. From GWA’s point of view, those terms were more consistent with its preference for keeping 20 percent of the account’s value uninvested.
On March 6, 2003, Deutsche Bank unveiled a pricing proposal setting forth financing fees for capital it would supply to the barrier contracts. Those fees were exactly the same as fees that Deutsche Bank took from ordinary customers for leverage in prime brokerage accounts, notes the Decision. With Doucette’s blessing, GWA’s executive committee approved GWA’s taking part in the barrier contracts.
On April 15, 2003, a “cross trade” gave Deutsche Bank the portfolio securities in the securities baskets underlying the RBC contracts that were set to terminate that very day. GWA made use of “cash events” to roll over its other RBC contracts and reported $59,439,344 worth of long-term capital gains arising from the closure of six RBC contracts, the Decision details.
That same day, GWA and Deutsche Bank entered into their first barrier contract. Although Deutsche Bank held title to the securities in the reference basket, GWA or one of its affiliates made use of a right to tell Deutsche Bank how voting rights for the shares in question would be exercised.
Reports that the bank put together stating the performance of the securities in the reference basket and the cash settlement that would come into play if the barrier contract were to end on that date were very similar to the monthly statements that prime brokerage customers received from Deutsche Bank, states the Decision. As in the case of the RBC options, GWA was entitled to receive settlement payments from shareholder-derivative and class-action lawsuits brought by companies whose stock the reference baskets held. In fact, on its 2009 tax return, GWA reported as long-term capital gains $127,925 that it had received from class-action settlement proceeds related to basket securities.
The Decision details how Weiss Associates directed trading in the reference basket, making use of strategies that “precisely mirrored” the long/short investment strategies that GWA and affiliates relied on in other contexts. On a nightly basis, Weiss Associates sent Deutsche Bank trade files that went straight into the bank’s order management system for execution the next day. Weiss Associates made trades of 268 various securities in the reference basket on a typical day and, in 2005, initiated 89,075 trades involving more than two billion units of stock, the Decision states.
The Launch of WMSA
The investment strategy worked out so well for GWA that, in 2005, it launched hedge fund WMSA, which would invest “outside” money as opposed to the “inside” money that principals of the firm had made available. From 2006 through 2010, Weiss acted as chairman and CEO of WMSA and Doucette as president, COO and head of risk management.
According to the Decision, Weiss Associates undertook a gradual transfer of its investment operations to WMSA, until the former entity was “a shell” by the end of 2006. WMSA investment teams, consisting of a portfolio manager, a trader and quantitative analysts, operated directly under Weiss, who also chaired an “allocation committee” figuring out what portion of funds under management would go to a given strategy, including the barrier contracts. GWA reaped huge payouts from the termination of certain barrier contracts and, in an April 20, 2006, addendum to its May 2001 private placement memorandum stated that its total capital stood at $149,558,658 and that “substantially all” those assets were “devoted to SFTIs, in particular the barrier options.”
The IRS’ Clarification of Ownership
On November 12, 2010, the IRS published Generic Legal Advice Memorandum No. AM2010‑005 (Memo), which addressed hedge fund basket option contracts and described the hypothetical case of a contract between a hedge fund and a foreign bank. The contract in that hypothetical closely resembled the actual barrier contracts in place between GWA and Deutsche Bank. The Memo clearly set forth the IRS’ view that such a contract was not an option and that the hedge fund owned the basket securities.
Just a day later, Deutsche Bank emailed Doucette a copy of the Memo. In a January 14, 2011, meeting, an unnamed Deutsche Bank official directly expressed concerns to Doucette about the implications of the Memo. Thus, the Tax Court concluded that Weiss understood that his hedge fund was operating outside stated law.
Fraudulent Tax Returns
In spite of knowing about the Memo and what it meant for GWA’s basket securities trading, Weiss and his associates filed a Form 1065 for the 2010 tax year on September 11, 2011, following the same approach as prior tax returns that had classified profits from six earlier basket contracts as long-term capital gains. GWA reported $182,678,910 as long-term capital gains arising from the termination of the seventh through tenth barrier contracts.
GWA’s tax return methodology, in its federal tax returns for 1997 and 1998, also made extensive use of mark-to-marketing, the Tax Court detailed. Under that methodology, GWA reported a gain or loss on a security held at the close of the taxable year as if parties had sold that security on the last business day of the year in question for its fair market value. The IRS did not agree with the methodology that GWA had used either in its classifications of long-term capital gains or its mark-to-marketing.
GWA filed its 1998 tax return approximately one year after executing its initial RBC options, the Tax Court noted. Had GWA sought to elect mark-to-market treatment for all its securities positions, it would have had to mark the RBC options to market at year-end 1998, it added. Instead, GWA reported $319,821 of “unrealized gains on investments.”
Failing to represent GWA’s direct holding of securities in its 1990 tax return, and indicating that such securities were held by OGI, was an act of knowing and deliberate tax fraud on the part of GWA, the Tax Court contended.
In the tax return, the Decision charges, GWA attempted to make use of an election that it did not legally have the right to employ, keeping from its mark-to-market election securities that it held directly rather than through OGI. “And here the evidence that appeared in GWA’s tax return was consistent with its intent,” the Decision states. “GWA could not possibly have intended to elect mark-to-market treatment for securities it held directly because that would have eviscerated the tax-deferential objective of the RBC ‘options.’”
The Decision takes particular exception to GWA’s practice of trading on Deutsche Bank’s “Trade Restricted List” by shifting the trades to OGI’s account and transferring securities positions from the managed accounts to the OGI account by cross-trading or position journaling, “free of transaction costs and without tax consequences.”
The Question of Ownership
In making a determination as to ownership of the basket securities – with all that such ownership implied for tax purposes – the IRS found it necessary to go far beyond nominal ownership (i.e., the bank’s) and look at a broad array of facts and circumstances, observed Mark Leeds, partner at Pillsbury. The ability of GWA to trade the securities or refrain from exercising the option until maturity – for potentially as long as 12 years – and thereby defer any tax obligations or liabilities for a commensurate period of time were critical considerations here.
In challenging the IRS, GWA tried to pursue a defense somewhat more limited in scope than the consideration of all relevant facts and circumstances might have warranted and, in particular, to emphasize the role of the banks with which GWA had entered into business, Leeds noted. “Beneficial ownership, or tax ownership, is based on the totality of the facts and circumstances,” he commented. “In this particular case, GWA exercised so much power over the securities within the basket that it would have been anomalous for the court to conclude that it wasn’t the owner.”
“The basis on which GWA took the position that it was not the beneficial owner related to creditor rights. In other words, the bank that wrote the derivatives was the nominal owner,” Leeds observed. “If the bank had gone bankrupt during the period in question, its creditors would have been able to foreclose on the securities held in the basket, because they weren’t held in a custody arrangement; they were owned by the bank.” It appeared that this contingent credit risk was the basis upon which GWA concluded it was not the owner of the basket components.
Unfortunately for GWA, the IRS had precedent to fall back on in making its case that GWA was, for all intents and purposes, the owner, Leeds noted. A February 1977 Tax Court ruling considered the question of whether Data Lease, with which Miami National Bank had filed a joint tax return, was the direct owner of shares in a subordinated securities account whose holder was First Devonshire. The tax commissioner concluded that, regardless of what rights the creditors may have held, the direct owner was not Data Lease but an individual named Samuel Cohen, even though the shares were held in the subordinated account. That conclusion has implications for subsequent matters in which courts must decide questions of beneficial ownership and attendant tax liabilities.
See “Hot Tax Topics for Private Fund Investors and Managers” (Jan. 21, 2021).
The Knockout Feature
A further consideration in determining beneficial ownership of the basket securities was the so-called “knockout feature” under which a decline in the value of the basket below a certain point would trigger termination of the contract and liquidation of the securities. From GWA’s viewpoint, that feature might have supported the notion that its ownership of the basket was limited and contingent. But that argument does not hold up to scrutiny, Leeds pointed out, because GWA could have defeated the knock-out by posting additional collateral.
As the Decision acknowledges, Deutsche Bank itself put in place a mechanism that GWA could use to preempt the knockout and avoid cancellation of the contract. In anticipation of circumstances in which the basket’s value appeared on course to fall below the threshold that would trigger the knockout, the bank gave GWA the right to pay it an additional premium to keep the contract active.
The IRS, in guidance set forth in 2024 and 2025, established that the ability to pay an additional premium to defeat a knockout was an indicator of ownership, pointed out Leeds. “The bank wasn’t in the business of taking an actual view on the underlying securities. The bank was acting as a dealer – just attempting to earn a dealer’s income from the writing of the option,” he noted. “So, if the value of the underlier fell below the amount by which the option was ‘in the money,’ and the bank had hedged itself under the option by buying the securities, it would have started to experience a loss itself.”
“It wasn’t as if these securities started off on the bank’s own balance sheet. The bank didn’t hold the securities. It just wanted to buy from X and sell to Y,” continued Leeds. “So if the value started to experience a loss, that’s not a dealer transaction.”
The existence of certain barrier options ultimately did not go far toward helping GWA prove its case, concurred Chaim Stern, special counsel at McDermott Will & Schulte. “The court disregarded the so-called barrier options and treated GWA as the tax owner of the underlying position. Given the facts of the case, it wasn’t a shocking decision,” he said.
It is understandable that some people might try to argue that the knockout feature of the arrangement was more indicative of a lending-type arrangement than an option, Stern acknowledged. “It goes back to the fact that the bank can effectively trigger a margin call. That is a feature that might lead some to view it more as a loan than an option,” he conceded.
But that argument does not really square with the common understanding of what barrier options are and how they function. Far from conferring beneficial ownership of the underlier to the optionee, barrier options are often tailored to protect the bank’s interests if prices rise too high. In that scenario, the bank relies on the “capped” feature of the options, Stern noted.
“Barrier options generally have features that protect the bank, and people still respect those as options,” said Stern. “The fact that they knock out when certain price points are hit doesn’t necessarily change that conclusion. That, itself, shouldn’t change the character of the option or the ownership of the underlier.”
In the end, GWA could not successfully downplay the rights it enjoyed with respect to the underlying assets or prove to the Tax Court that the bank was the beneficial owner. “If you have the right to trade and dispose of the underlier in the manner that you see fit, that is a feature of ownership – even more so than the fact that the bank has the right to unwind the contract if the collateral price falls,” Stern observed.
Accounting Method Change
An obvious potential hurdle to the IRS in its action against GWA is the sheer amount of time that had passed since the filing of the faulty tax returns. In theory, the IRS commits to limiting the scope of audits to the prior three years, or six years if it believes it has identified a significant error, although it reserves the right to go back further.
In Stern’s view, an unusual and significant aspect of the case is the reasoning the Tax Court used to get around the statute of limitations that otherwise might have protected GWA. “The biggest novelty is that the court considered its own position to be an accounting method change, which is how it effectively extended the statute of limitations,” he said. “You wouldn’t normally consider a change that is forced on the taxpayer – a court ruling – to be an accounting method change for purposes of extending a statute of limitations, but that is what the court decided.”
“The only reason for the technical classification of the IRS’ adjustment as an accounting method change is because the IRS has gotten so far outside the statute of limitations,” Stern posited. “It had to make the adjustment into an accounting method change because it wanted to extend the statute.”
See “Navigating the Uncertain U.S. Tax Landscape” (Jan. 13, 2022); and “Key Tax Issues Fund Managers Must Consider” (Jun. 10, 2021).
Attorney-Client Privilege
In the Tax Court’s view, GWA sought to escape responsibility for its fraudulent dealings by claiming to have exercised due diligence by getting expert opinions from tax lawyers in 2009 and 2011. During the discovery process, the Decision explains, GWA relied on attorney-client privilege, however, to avoid having to share with the IRS the content of its communications with the tax attorneys in question.
Although it does not challenge the claim that GWA did seek out expert tax advice in the two years in question, the Tax Court maintained that, without those legal opinions in the official record, “we are unable to ascertain the extent (if any) to which they could reasonably support GWA’s tax return positions.”
In Stern’s view, it would be a mistake to assume that, had GWA not invoked attorney-client privilege, it could have made a successful “reliance on professional advice” defense. “The court was concerned that the taxpayer had asserted attorney-client privilege inconsistently for some things and not for others. We cannot know exactly what it would have done if the taxpayer had been more open about its tax advice,” he said.
See “Understanding the Fiduciary Exception to Attorney-Client Privilege” (Aug. 17, 2023).
Takeaways
According to Stern, the terms of GWA’s arrangements are not favorable to its case. The prospect of challenging the Decision on the grounds of the statute of limitations offers slightly more hope than trying to defend the characterization of the arrangements as options in accordance with their form. As for potential tax law complications, it makes sense for registered entities to steer clear of certain types of arrangements altogether, in keeping with repeated IRS guidance.
“In my practice, I counsel people to stay away from arrangements that give the taxpayer the right to trade the underlier. I tell people that that doesn’t work,” Stern shared. “It has been the focus of the IRS in its guidance in 2010 and then again in 2015. The closer you are to a traditional option, the better off you are. You really want to have something that has the economic characteristics of an option, rather than a lending arrangement.”
Moreover, from an operational standpoint, GWA made some serious mistakes that could not have helped its legal position in the matter, Stern suggested. “There were unhelpful background details here, such as cross-netting against GWA’s other accounts. It wasn’t done on a form that was fit for purpose. There were various disclosures that were not helpful to their fact pattern,” he said. “Basically, the evidence suggested that the substance of the arrangement was inconsistent with its reported form – it suggested that the petitioner was simply borrowing on margin to finance its own trading positions.”
See our two-part series: “Synopsis of the IRS Partnership Audit Process and How It Can Be Addressed in Fund Documents” (Jun. 16, 2022); and “Modifications, Amended Returns and Push-Out Elections as Cures for Imputed Underpayments From IRS Partnership Audits” (Jun. 23, 2022).
