A bank's overdraft notice set off a disciplinary case that now has the Supreme Court of Maryland weighing whether to disbar Tiffany Fountaine Boykin, Montgomery College's dean of Rockville Student Affairs. Findings in the case say Boykin made 54 transfers from her client trust account to her law firm's operating account, moving nearly $28,000 that she then spent — plus a little more — at ATMs while gambling.
The case did not begin with an angry client filing a complaint. According to the Maryland Daily Record, it started when Boykin's bank flagged an overdraft and alerted bar counsel. From there, investigators say they found a pattern: dozens of transfers out of a trust account meant solely to hold client money, feeding a firm operating account and, from there, cash withdrawals for gambling.
Boykin's attorney, Marc Eisenstein, has pushed back hard on the characterization that any of it was intentional. He argued his client believed she had earned the money she moved, and said she simply failed to send invoices to numerous clients that would have matched up with the trust-account transfers — in his telling, a recordkeeping failure rather than theft, per the same account.
Bar Counsel Alleges a Pattern of Deception
Assistant bar counsel W. Hunter Daley offered a starkly different version of events. Daley characterized the case as involving intentional dishonesty and deceitful conduct nearly at every turn, telling the court that Boykin knew how to properly invoice her clients and simply didn't — not because she forgot, bar counsel argued, but because doing so would have exposed the transfers.
Daley also said some periods saw numerous transfers from the trust account to the operating account with no invoices or client-related notations attached at all, and that some invoices Boykin did send misrepresented how much money was actually being held in trust on clients' behalf. The findings further state that Boykin made several false statements in her initial response to bar counsel and multiple false representations to the federal government to obtain loans for her solo practice.
One episode highlighted in the findings involves a Zelle transfer with the word “gamble” written in the memo line. Boykin said the transfer could have been for gambling or for a client surnamed Gamble — but the findings state she had no client by that name.
Boykin's Gambling Testimony
Boykin testified that her gambling began as a way to relax and escalated over time, in both the amount of money and the hours she spent on it. She said she believed it remained under control because, in her words, she had not gambled away her mortgage or left her children unfed.
The disciplinary record shows Boykin has since voluntarily stopped practicing law. She also left her position as general counsel at Anne Arundel Community College in 2025 while the bar counsel investigation was ongoing. Montgomery College has confirmed that Boykin remains its dean of Rockville Student Affairs, and the college said it was aware of the matter but declined further comment.
What the Evidentiary Hearing Found
Baltimore County Circuit Judge Marc A. DeSimone Jr. held an evidentiary hearing in May and found that Boykin's unauthorized trust-account transfers and casino cash withdrawals sullied the legal profession. Boykin participated in oral arguments before the Supreme Court of Maryland on Wednesday as the justices consider what discipline to impose.
Maryland's trust-account rules are explicit about situations like the one described in the findings against Boykin. Under Maryland's attorney conduct rules, Rule 19-301.15 governs the safekeeping of client property and Rule 19-407 sets record-keeping requirements for attorney trust accounts — rules that took effect statewide on July 1, 2016.
How Other Maryland Disbarment Cases Have Turned Out
Maryland's high court has disbarred attorneys before in cases involving intentional misuse of trust funds. In 2022, the court disbarred attorney Lawrence Daniel O'Neill after finding he misappropriated client funds, mishandled his trust account and made false statements to bar counsel; the court's opinion noted O'Neill's account carried a negative balance on ten separate occasions between July 2018 and September 2019, per Maryland Courts records. In that ruling, the court distinguished intentional misappropriation from mere negligence, writing that unlike an attorney who acted negligently, O'Neill had intentionally misappropriated and commingled funds.
A more recent case out of Montgomery County ended the same way. The Maryland Daily Record reported in September that the Supreme Court of Maryland disbarred attorney Arya Saleh after a circuit court judge found he had solicited a $1,000 gift from a client, overdrew his trust account to cover childcare expenses, and committed perjury during a bar counsel investigation. That judge found Saleh had used trust funds to pay his family's longtime childcare provider, a practice that eventually left an expert witness's check bouncing for insufficient funds.
Those cases do not determine what the Supreme Court of Maryland will decide for Boykin. The court's November argument calendar lists the matter as Attorney Grievance Commission v. Tiffany Fountaine Boykin, but no ruling or timeline for one has been made public.
