Jonathan Vincent Glenn, 55, of Greenwich, Connecticut, spent three decades on Wall Street, entering the industry in 1993 with Kidder, Peabody and later working at UBS PaineWebber, Merrill Lynch, Morgan Stanley, and Wells Fargo before founding his own firm, GlennCap LLC, also known as Glenn Capital, an investment advisory firm headquartered in the wealthy Fairfield County town of Greenwich. Through GlennCap, Glenn provided portfolio management services to clients, selecting assets and allocating trades on their behalf. Between January 2020 and March 2022, he used that discretion to defraud his own clients through a practice called cherry-picking: he placed block trades in GlennCap’s omnibus brokerage account, waited to see whether the positions rose or fell in value during the day, and then allocated the profitable trades to his own accounts, his family’s accounts, and favored client accounts, while assigning the losing trades to disfavored clients. He defrauded more than 45 clients of more than $2.7 million. On August 14, 2026, the SEC issued an order transferring the Fair Fund it had established in the case to the U.S. District Court for the District of Connecticut, to be distributed to Glenn’s victims under the criminal restitution order.
The August 2026 order is the final financial chapter in a case that had already produced both civil and criminal judgments. On September 14, 2023, the SEC found that GlennCap and Glenn willfully violated the antifraud provisions of the Securities Act, the Exchange Act, and the Investment Advisers Act, and ordered them to pay, jointly and severally, disgorgement of $2,743,616 and prejudgment interest of $251,357, with Glenn ordered to pay a $500,000 civil penalty. In the parallel criminal case, Glenn pleaded guilty to securities fraud on October 5, 2023, admitting he harmed more than 45 victim clients who collectively lost more than $2.7 million. U.S. District Judge Robert N. Chatigny sentenced him on September 17, 2024, to 21 months in federal prison followed by three years of supervised release, with the first six months in home confinement, and entered a restitution order for $2,743,616. He reported to prison on December 2, 2024.
Block Trades Held in an Omnibus Account Until the Winners Could Be Sorted From the Losers
The mechanism of Glenn’s fraud is the classic architecture of cherry-picking. When an adviser places a block trade, he buys a large quantity of a security in a single omnibus account and then allocates portions of that block to individual client accounts. Done honestly, the allocation is decided in advance or by a neutral formula, so that all clients share proportionally in the gains and losses. Glenn did it dishonestly. He placed the block trades in GlennCap’s omnibus brokerage account and then waited, sometimes until later in the same day, to see how the positions performed before deciding which accounts would receive them. When a block purchase of an equity security increased in value in the hours after it was bought, Glenn generally sold it and allocated the profit to favored accounts, including his own accounts, his family members’ accounts, and certain client accounts. When a block purchase decreased in value, he generally allocated it to the non-favored client accounts. The clients absorbing the losing trades had no idea their adviser was routing the day’s winners to himself.
The deception was compounded by what Glenn told his clients about how he operated. He did not inform them that he was cherry-picking. Instead, he gave them the false impression that he allocated trades fairly and according to a predetermined allocation methodology. Clients who believed their adviser was following a neutral, consistent process for distributing trades were in fact being systematically assigned the losing side of his trading while he kept the winning side. The SEC also found a fee dimension to the favoritism: among the favored accounts were client accounts that paid GlennCap a higher percentage of positive returns in fees, giving Glenn a direct financial incentive to steer profits to those accounts alongside his own.
A Statistical Pattern That Does Not Happen by Chance
Cherry-picking is detected the same way in nearly every case: through the statistical improbability of the allocation pattern. When an adviser allocates trades fairly, the favored and disfavored accounts should experience broadly similar rates of first-day gains and losses, because they are participating in the same block trades. When an adviser cherry-picks, the favored accounts show a disproportionate share of trades with positive first-day returns and the disfavored accounts show a disproportionate share of negative ones, a divergence too large and too consistent to be explained by chance. Glenn allocated a disproportionate number of trades with positive first-day returns to his favored accounts and a disproportionate number of trades with negative first-day returns to other client accounts over a period spanning January 2020 to March 2022. This same statistical signature has anchored a series of recent enforcement actions against advisers who abused block trading, including the case against Gregory Zandlo of North East Asset Management, whose favored accounts saw winning days at nearly three times the rate of his clients’ accounts, and the action against Matthew Werthe of HSR Wealth Management, who was ordered to pay $1.1 million for the same practice.
A Fair Fund Now Routed Through the Criminal Restitution Order
The August 2026 order resolves how the money Glenn and GlennCap paid will reach the victims. When the SEC settled its case in 2023, it created a Fair Fund under the Sarbanes-Oxley Act to distribute the civil penalty, disgorgement, and prejudgment interest to harmed investors. GlennCap and Glenn have so far paid a total of $941,767.86 into that fund. Because the criminal restitution order covers the same $2,743,616 loss and the same victims, and because all the investors who would receive a Commission distribution are also on the criminal restitution victim list, the SEC determined the most efficient path was to transfer the Fair Fund, and all future funds returned to it, to the U.S. District Court for the District of Connecticut as partial payment of Glenn’s restitution debt. The victims will be paid through the court’s restitution process rather than through two parallel distributions. This coordination between the SEC civil Fair Fund and the criminal restitution order is a common feature of cases where an adviser faces both proceedings, as with the parallel civil and criminal resolutions documented in the Western Asset cherry-picking matter involving former star manager Ken Leech.
A 30-Year Career That Ended in Prison and a Revoked Registration
Glenn’s fall was steep. He had spent 30 years at some of the most recognized names on Wall Street before opening his own firm in Greenwich, one of the wealthiest communities in the country and a hub of the investment management industry. The state of Connecticut revoked GlennCap’s investment adviser registration, permanently barred the firm from operating as a broker-dealer or investment adviser, and barred Glenn personally from doing business in the state for seven years. The securities fraud count to which he pleaded guilty carried a statutory maximum of 25 years in prison and a fine of up to approximately $5.4 million, though his actual sentence was 21 months. He is required to make full restitution of the $2.7 million his clients lost. The 45 clients who trusted a three-decade industry veteran to manage their money fairly were, for more than two years, systematically handed the losing half of his trades while he kept the winning half for himself and his family.
Conclusion
Jonathan Glenn built a 30-year Wall Street career and his own Greenwich advisory firm, and then used the discretion his clients granted him to steal from them. For more than two years he placed block trades in GlennCap’s omnibus account, waited to see which ones rose in value, and gave the winners to himself, his family, and the clients who paid him the highest fees, while dumping the losers on 45 other clients who were told he allocated trades fairly. He took $2.7 million. He pleaded guilty, was sentenced to 21 months in prison, and reported to prison in December 2024. In August 2026 the SEC routed its Fair Fund into the court’s restitution process so the victims could be repaid. The clients believed their trades were being allocated by a neutral methodology. The methodology was that Glenn kept the winners.
