Milton Grimes, who is among a bevy of lawyers who successfully pushed no fewer than 17 of San Bernardino County’s 24 municipalities into adopting by-district city/town council elections between 2014 and 2024 by either veiled or more direct accusations of racial bias in the way those jurisdiction’s choose their elected leadership, was sentenced on Tuesday to 18 months in federal prison for evading the payment of more than $7.2 million in federal and state taxes over a period of more than two decades.
Grimes was sentenced by United States District Judge Stanley Blumenfeld Jr., who also ordered him to pay $7,236,556 in restitution, both to the Internal Revenue Service and to the California Franchise Tax Board.
In October 2024, Grimes pleaded guilty to one count of tax evasion relating to his 2014 taxes and admitted that he failed to pay $1,690,922 to the IRS.
“Despite being a respected attorney, Mr. Grimes also made the deliberate decision to cheat on his taxes for decades, evading the payment of millions of dollars in tax that all citizens are required to pay,” said Acting United States Attorney Joseph T. McNally. “Tax fraud has a corrosive effect on society’s foundations, and we thank our partners at the Internal Revenue Service for their diligence in bringing this defendant to justice.”
“As a successful attorney and owner of a law practice, Mr. Grimes was well aware of his income tax obligations, which he repeatedly chose to evade,” said Los Angeles Internal Revenue Service Field Office Special Agent in Charge Tyler Hatcher. “Despite multiple attempts by the IRS to help him settle his tax obligations, Mr. Grimes continued to obfuscate his income. Unfortunately for him, IRS criminal investigation special agents are the best financial investigators in the world, and now he will feel the repercussions of his actions.”
Grimes did not pay federal income taxes due for 23 years, 2002 through 2005, 2007, 2009 through 2011, and 2014 through 2023, according to federal prosecutors. The amount owed totaled $5,921,260, including tax, penalties, and interest owed to the IRS, according to documents filed in conjunction with his case. Grimes also admitted he did not file a 2013 tax return with the IRS.
In addition to the federal tax evasion, Grimes admitted that he owed over $1,313,231 in delinquent state taxes to the California Franchise Tax Board from 2014 to 2023.
Beginning in September 2011, the IRS attempted to collect Grimes’ taxes by issuing more than 30 levies on his personal bank accounts. However, from at least May 2014 to April 2020, Grimes willfully evaded the payment of the outstanding income tax owed to the IRS by not depositing income he earned from his clients into his personal bank accounts that were subject to levy, according to the U.S. Attorney’s Office.
Instead, Grimes purchased approximately 238 cashier’s checks totaling $16 million to keep the money out of the reach of the IRS, according to affidavits filed in federal court by federal agents. Grimes would routinely purchase cashier’s checks and withdraw cash from his client trust account, his Interest on Lawyers’ Trust Accounts (IOLTA), and his law firm’s bank account, rather than pay the IRS, prosecutors alleged.
An example of this consists, federal officials maintain, of Grimes purchasing, on December 5, 2018, nine cashier’s checks worth approximately $1,001,961, following the deposit of the same amount and on the same date into his Interest on Lawyers’ Trust Accounts bank account.
The IRS Criminal Investigation unit in Los Angeles investigated this matter.
Assistant United States Attorneys Valerie L. Makarewicz and Sarah S. Lee of the Major Frauds Section prosecuted the case.
Grimes is to begin serving his sentence on June 3.
Grimes has had a storied career as a member of bar in California.
Born in South Carolina as the grandson of a North Carolina sharecropper, Grimes spent much of his youth in North Carolina and Virginia, where as a teenage he experienced firsthand what he characterized as “brutality” vectored at African-Americans by civil authorities, most particularly the police, who had, he said, “pointed guns at my head on more than one occasion.”
He studied at West Virginia State University, from which he graduated in 1967. He subsequently was accepted into Hastings College of Law in San Francisco, from which he graduated in June 1973, and was admitted to the California Bar in 1974.
Despite invitations to join several major firms, Grimes opted to function professionally as a solo practitioner or in small firms in which his independent approach would not be restricted by senior partners. He was also accepted into the bar in Arizona, Hawaii, Illinois, Louisiana, Mississippi, Missouri, Oregon, Washington, New Mexico, New York, North Carolina, Nevada, West Virginia, Washington, D.C. and Pennsylvania, where he was the lead defense attorney on a multitude of federal and state criminal cases, including murder cases in which prosecutors were seeking the death penalty, as well as major drug cases, rape cases and fraud cases. He also handled a handful of civil cases in a few of those jurisdictions, including wrongful death trials. He was admitted to the state bar in Texas, where he handled a major civil case.
In California, by the 1980s, he was handling a large number of cases in both Los Angeles and Orange counties. He first came to national attention with his representation of Sheryl Lynn Massip, an Anaheim woman who was charged with and convicted of second-degree murder in the death of her six-week old son, whom she had run over while driving the family’s Volvo.
In his representation of Massip, Grimes convinced Orange County Superior Court Judge Robert R. Fitzgerald, who was known for being unforgiving to those convicted of serious crimes and meting out extremely harsh sentences, to instead of assigning her to prison for life to enter an acquittal, reversing the jury’s guilty verdict.
Massip had to be mentally deranged, Grimes told Fitzgerald, since “no mother in her right mind would have done what she did.”
The Massip case marked the first time the use of a postpartum psychosis defense had ever succeeded in Southern California.
Thereafter, Grimes successfully applied the use of insanity or diminished capacity defenses in a number of trials.
At the same time, Grimes, true to his roots, took on a number of police brutality cases, civil filings largely on behalf of African American or other minority clients. Those included a case in federal court relating to a 1983 police shooting case in Sacramento and the beating administered by police in 1990 to several young men at a Red Onion restaurant in Santa Ana. It was on the strength of some of those cutting-edge legal battles that Rodney King, the motorist who was beaten senseless by four Los Angeles police officers during a traffic stop, ditched the attorney who was representing him, Steven Lerman, for Grimes. The City of Los Angeles, which had previously offered King a $1.75 million settlement, was forced to more than double that amount by Grimes, who pushed forward with the matter, ultimately obtaining a $3.8 million settlement.
Beginning in 2013, Grimes joined with Lancaster-based attorney R. Rex Parris, Malibu-based barrister Kevin Shenkman and Los Angeles-based solicitor Matthew Barragan, who has since gone to work for the U.S. Attorney’s Office, to collectively generate for themselves over the next several years $7 million in legal fees by exploiting a provision in the California Voting Rights Act that entitles a lawyer seeking to promote so-called protected minority voter empowerment to bill the cities they engage with in that effort.
A fair number of the cities the four lawyers exploited in this way were in San Bernardino County. In 2013, Parris, Shenkman and Grimes opportunistically surveyed the San Bernardino County landscape and selected what they considered to be the county’s most vulnerable jurisdiction among a handful of cities perceived to have foreclosed minority rights because of the relative scarcity of elected Hispanic officeholders locally despite the region’s substantial Latino population.
Thus, Parris, Shenkman and Grimes in 2014 settled upon the City of Highland, where despite more than 39 percent of the residents of that city being Latino, no Hispanics at that time were serving on the city council. Highland thus became the first San Bernardino County city served with a demand that it alter the way it elects its council members. Highland responded by placing an initiative, Measure T, on the ballot asking the city’s voters whether they wanted to switch to by-district elections. When the city’s voters in November 2014 rejected Measure T, with 2,862 votes or 43.01 percent in favor and 3,793, or 56.99 percent opposed, Parris, Shenkman and Grimes proceeded with the lawsuit on behalf of Lisa Garrett, a resident of Highland who claimed to be politically disenfranchised because she was Hispanic.
Upon the matter going to trial, despite making a finding that the socio-economic-based rationale presented by the plaintiff’s attorneys to support the need for ward elections was irrelevant and that Garrett’s assertion district voting was the only way to cure the alleged violation of the Voting Rights Act was false, San Bernardino Superior Court Judge David Cohn mandated that Highland adopt a ward system. For their efforts, Parris, Shenkman and Grimes experienced a $1.3 million payday.
Thereafter, Matthew Barragan, who was then the staff attorney representing the Mexican American Legal Defense Fund known by the acronym MALDEF, and Parris, Shenkman, Grimes threatened lawsuits under the California Voter Rights Act against the cities of Barstow, Big Bear Lake, Chino, Chino Hills, Hesperia, Rancho Cucamonga, Redlands, Twentynine Palms, Upland and Yucaipa, as well as the towns of Apple Valley and Yucca Valley. Later, they would lodge such demands with the cities of Fontana and Ontario.
A provision of the California Voting Rights Act was that a city hit with a demand that it move to by-district or ward voting could seek a “safe harbor” from the ruinous storm of potential litigation and get out from under the accusation that as a community its members had engaged in racially polarized or ethnically polarized voting by simply agreeing to make the voting system transition to wards or districts and paying the attorney/attorneys making such a challenge a fee of $30,000 to $45,000.
In a number of San Bernardino County’s municipalities, city officials and residents where racially polarized voting had been alleged expressed umbrage at that suggestion and denied the assertions that there was a systemic or institutionalized racial or ethnic bias built into their political establishments. Nevertheless, the prospect of having to wage a legal battle that, if won, would cost the city its own legal costs, and if lost, could run into the millions of dollars, persuaded city council after city council to simply fold and accept a transition to district voting without a fight.
Those lawyers seeking a quick $30,000 to $45,000 payday or a larger payout by actually filing suit against cities to force them into district-based elections avoided some San Bernardino County cities, particularly those which had a clearly demonstrable history of electing minority – generally, Hispanic – civic leaders. Among those were San Bernardino and Colton, which had long histories of electing Latino and Black council members and had already switched to district voting, as well as Rialto, Needles, Grand Terrace, Montclair and, initially, Victorville, where their city councils had proven to be highly diverse.
In a number of cases in San Bernardino County, the quartet of Parris, Shenkman, Grimes and Barragan bulled their way ahead, however, bullying city officials and their taxpayers and voters into accepting by-district voting through their employment of a one-sided provision of the California Voter Rights Act. That provision pertained to the legal fees that could be or could not be assessed against the loser in such litigation. If a city fought a lawsuit brought under the California Voter Rights Act and it lost, it was liable for the legal fees paid out by the prevailing party. However, if a city fought a lawsuit brought under the California Voter Rights Act and it won, it could not, as the prevailing party, recover its legal fees from the losing party. Thus, Highland lost $1.3 million in fighting Parris, Shenkman and Grimes and Rancho Cucamonga, which counted among its roster of elected council members Hispanics and African Americans, lost $1.37 million to Parris, Shenkman, Grimes and Barragan when it sought to maintain its at-large voting system.
This bullying carried over to Victorville. In that city, in the thirty years between 1991 and 2021, Victorville’s voters had elected a total of 20 council members, eight of whom – Felix Diaz, Rudy Cabriales, Angela Valles, Gloria Garcia, Eric Negrete, Blanca Gomez, Rita Ramirez and Elizabeth Becerra – were Latino or Latina and two of whom – Jim Busby and Leslie Irving – were African American.
Despite that, in 2021, Scott Rafferty, alleging that Victorville had been plagued with racially/ethnically-polarized voting, demanded that the city transition to district elections. Despite Victorville City Attorney Andre deBortnowsky’s insistence that the city had not engaged in racially/ethnically polarized voting, in the face of Rafferty’s effort to force the city to embrace ward system voting, he nevertheless recommended that the city knuckle under and accede to moving to ward system voting as Rafferty was proposing, since even were the city to roll the dice and prevail in resisting the changeover, it would not be able to recoup the legal costs of engaging in that defense, given the terms of the California Voting Rights Act.
Rafferty, intimating that he would tolerate no delays in the city moving to a ward/district voting system, and using the cudgel bequeathed to him by the California Voting Rights Act and the demonstration by his fellow attorneys Parris, Shenkman, Grimes and Barragan of how it could be employed, successfully stampeded Victorville into making the change, collecting in the process $45,000 in exchange for writing a half dozen letters and making five phone calls.
Ultimately, Parris, Shenkman, Grimes, Barragan and Rafferty simply collected their money and walked away, without following up on what they had wrought or ensuring that the “reforms” they had forced upon San Bernardino County’s various cities delivered the diverse representation they said they were striving toward.
In actuality, in case after case, the existing city councils used the electoral map drafting process that came with the transition to voting wards to gerrymander the districts they created such that in the vast majority of cases what came to pass were districts that virtually ensured the continuing electability of the incumbents. In several though not all instances, what actually occurred is the shrinking of the jurisdictions in which the politicians had to run made it easier for the incumbents to prevail. Those incumbents generally used the advantage of their incumbency to collect money from donors who had business before the city and then applied that money to fund their campaigns, consisting of phone banking for surveys and promotion, lawn signs, radio and television spots, handbills and mailers promoting themselves and hit pieces attacking their opponents, along with bumper stickers, billboards and other advertisements. Because they could concentrate that electioneering material among a smaller number of constituents, saturating a smaller geographical district with campaign blitz, those incumbents virtually assured their several reelections. In the vast majority of cases, what this effectuated was the lessening of minority representation or the prospect thereof.
Having now practiced law for 50 years, Grimes has tried, from start to finish, more than 310 jury trials.
While what has befallen Grimes is unfortunate, San Bernardino-based attorney Gary Wenkle Smith said it does not obviate Grimes’ value to the legal profession or society.
“I first met Milton in January 2000 at a regional seminar for trial lawyers,” Smith said. “He was at that time a member of the faculty and later the president of the board of the Trial Lawyers College. Eventually it split off from Gerry Spence, but the college continued on, despite litigation I am not supposed to talk about, but the forum continued to exist, in large measure because of Milton’s efforts and energy. There would quite literally be no Trial Lawyers College today without him. Milton is a brilliant trial lawyer, one of the leading trial lawyers in the country. He does not run away from the issues, and one of the issues involved in the legal profession is race.”
Smith said, “As a white man, and all of the things I have gone through, I got along fabulously with him, a black man, with all the things he had gone through, not just in his professional career but growing up. He is one of those rare people who can reach out to others even though he had experienced a lot of pain and anger. Despite that, he is still kind, tender, loving and respectful. He very obviously has anger about the things he has seen and experienced, but he never let that affect him or stop him from trying to share what he knows so we understand these things and we can be of benefit to our clients. He puts his heart into everything that he does all of the time. He has never failed, never wavered with regard to training trial lawyers. I trained with him at least twice a year for the past 25 years so I could be a better trial lawyer.”
Smith said, “I have been fortunate to spend personal time with him. He has helped me to understand myself better and by that be a better trial lawyer.”
Smith said, “During the college sessions he would use psychodrama as a tool. One year, we were doing an exercise in voire dire [jury selection] and he assumed the persona of Martin Luther King as we were moving through the process of jury selection. He was aiming at having people understand or imagine what Martin Luther King had gone through and he was doing this to have people express themselves freely, to find out what they had been through and he then asked, while he is in the persona of Martin Luther King, before a mixture of people, black and white, but mostly white, this question: ‘Did I waste my life? Was my life in vain? Was the work of my life for no good cause?’ He showed that amazing things come out of people when they talk from the heart. He encouraged everyone to get a different perspective.”
Smith said, “So, I spent 25 years working with him on those kind of things. I can’t think of a better human being in this world today. He has been a big part of people’s lives for so many years. getting down to the nitty gritty, talking about things from the soul, making us better lawyers. He is still recognized nationwide as one of the leading attorneys in the country. He made a mistake and it has cost him, but he’ll come out of this and still be able to take the initiative in making the community we live in a better place.”