Jerome Jacobson and the $24M McDonald’s Monopoly Scam

The McDonald’s Monopoly scam was a twelve-year fraud in which Jerome Jacobson, the head of security at the marketing firm that printed the game pieces, stole nearly every high-value winning piece and funneled them to a network of friends, relatives, and criminal associates who posed as legitimate winners. The scheme cost McDonald’s an estimated $24 million in cash and prizes before the FBI shut it down in 2001.¹ Jacobson pleaded guilty, drew 37 months in federal prison, and was ordered to pay more than $12.5 million in restitution.²

The Man Running Security Was the One Stealing

Jacobson had worked four years as a Florida police officer before joining Simon Marketing Inc., the firm McDonald’s contracted to produce and distribute game pieces for its promotional contests. As director of security, he oversaw the printing, transport, and application of game pieces to food packaging at production centers around the country. His job was to make sure nobody stole the prizes.¹

He took his first piece in 1989, a $25,000 winner he handed to his stepbrother Marvin Braun. The two split the money. That partnership reportedly ended after Jacobson gave Braun a million-dollar piece and Braun flushed it down the toilet.³ When McDonald’s raised the grand prize to $1 million in 1995, the operation accelerated. Over the full run of the scheme, Jacobson admitted to taking roughly 60 winning pieces.¹

How He Beat the Security Protocol

On paper, the system was tight. Jacobson personally carried the pieces in a briefcase secured with holographic, tamper-proof seals, and an independent accounting-firm auditor accompanied him at all times to keep the winning pieces sealed until they reached the packaging plants.⁴

Two cracks let him through. A foreign supplier of the holographic seals mistakenly shipped a batch directly to him, giving him his own stash of the stickers used to close the envelopes.¹ And the auditor could not follow him into the men’s room. On the way to packaging facilities, Jacobson would excuse himself to an airport bathroom stall, slit open the sealed packets with a small knife, swap the winning pieces for non-winners, and reseal everything with his stolen holograms. He wore a bulletproof vest during the handoffs to project an air of seriousness, and he picked up the auditor’s briefcase combination simply by watching the man enter it.⁴

The Network of Fake Winners

Jacobson could not claim the prizes himself, so he sold pieces to associates for upfront fees that typically ran $45,000 to $50,000 each. He also required that winners redeem the pieces in states different from where he had stolen them, keeping clusters of winners from showing a pattern.¹

He built a sprawling pyramid of recruiters who found people willing to pose as legitimate winners. His nephew Mark Schwartz became one of the most prolific. Members of a classic-car club Jacobson belonged to joined early, as did a Florida gambler and ex-convict named Andrew Glomb, who passed winning pieces to his own circle.¹

The ring took on a darker edge after Jacobson met Gennaro “Jerry” Colombo at the Atlanta airport. According to the HBO docuseries on the case, Colombo had ties to the Colombo crime family. His brother and widow said in the series that a figure known as “Uncle Dominic” connected Jerry to Jacobson around 1995.⁵ Colombo recruited winners, charged them up to $50,000 for a piece, and took half their prize money on top of that.³ His widow Robin later said she had warned him that the parade of Italian surnames among East Coast winners would eventually draw attention.⁶ Jerry Colombo died in a 1998 car crash in Georgia and never saw the scheme collapse. Federal authorities said the broader network stretched from drug traffickers and strip-club owners to psychics.⁷

The St. Jude Game Piece

One of the stranger episodes came in late 1995, when Jacobson anonymously mailed a $1 million winning piece to St. Jude Children’s Research Hospital in Memphis. The envelope was postmarked November 24, 1995, in Dallas, and the piece arrived at the hospital on December 4.⁸ Contest rules technically prohibited transferring game pieces, but McDonald’s chose to honor the donation. Ed Rensi, then president and CEO of McDonald’s USA, said “it was immediately obvious what the right thing was to do.”⁹ The company agreed to pay the prize in $50,000 annual installments over 20 years and said after the fraud came out that it had no intention of asking for the money back. Prosecutors later said Jacobson sent the piece only after failing to find an associate who could cash it before the contest deadline, and that he told people he hoped the gesture might buy him leniency if he were ever caught.

How the FBI Caught Him

The fraud unraveled through a family dispute rather than detective work. According to the HBO series McMillion$, the tip came from Jerry Colombo’s mother, known in the show as “Ma Colombo,” who contacted the FBI during a custody fight over her grandson in an effort to hurt her daughter-in-law Robin’s family.¹⁰

The tip landed on the desk of FBI Special Agent Doug Mathews in Jacksonville, Florida. A note mentioned a McDonald’s Monopoly con run by someone called “Uncle Jerry.”¹¹ Mathews opened an investigation he called Operation Final Answer and ran an unconventional sting: agents posed as a video production crew filming promotional interviews with McDonald’s contest winners, which let them travel with suspects, build rapport, and gather evidence. Former FBI videographer Jan Garvin helped make the cover story believable, and Tom Kneir, the special agent in charge in Jacksonville, authorized Mathews to work undercover without the bureau’s standard training. The point was to put targets at ease so that when their phones were later wiretapped, they would still talk freely.¹²

Arrests, Guilty Plea, and Sentences

On August 21, 2001, Jacobson and seven co-conspirators were arrested on felony complaints charging conspiracy to commit mail fraud under 18 U.S.C. §§ 371 and 1341, filed in the U.S. District Court for the Middle District of Florida.¹³ A broader indictment on September 7, 2001, added 20 defendants, and a December 6, 2001, indictment ultimately charged a total of 43 people with conspiracy to commit mail fraud.¹⁴

Jacobson pleaded guilty in April 2002, drew 37 months in federal prison, and was ordered to pay more than $12.5 million in restitution.²¹⁵ He was released on October 21, 2005.¹⁶ In total, 52 members of the conspiracy were convicted of mail fraud and conspiracy.⁷ Andrew Glomb and nephew Mark Schwartz, both prolific recruiters, each got just over a year. William Fisher, who had collected $1 million in 1996, received about three years of probation and $300,000 in restitution.¹ Robin Colombo also served prison time.⁶

Four Convictions Thrown Out on Appeal

Not every conviction held. Four defendants — George Chandler, Jerome Pearl, Kevin Whitfield, and John Henderson — took their conspiracy convictions to the Eleventh Circuit, and in 2004 a three-judge panel found “a complete failure of proof” and vacated them.¹⁷ The court described a “rimless wheel” conspiracy: the four had no connection to each other or knowledge of Jacobson’s broader embezzlement, so prosecutors had proved multiple separate conspiracies rather than the single one in the indictment. The ruling also held that violating the rules of a private contest did not by itself amount to criminal mail fraud, a meaningful limit on the government’s theory.¹⁴ The four were acquitted and restitution orders of up to $786,500 each were rescinded. Jacobson’s own conviction was untouched.

What It Cost McDonald’s and Simon Marketing

McDonald’s severed its relationship with Simon Marketing as soon as the fraud came out. The two companies sued each other for breach of contract. McDonald’s claim was ultimately thrown out, and the company was ordered to pay Simon Marketing $16.6 million in settlement.¹ Simon Marketing could not survive the reputational damage and announced plans to close and liquidate in 2002. Documentary co-director Brian Lazarte said the scandal cost thousands of employees their jobs across companies connected to the promotion.¹⁸

To patch customer trust, McDonald’s ran a $10 million instant cash giveaway distributed among 55 randomly selected winners. Then-CEO Jack Greenberg said “McDonald’s is committed to giving our customers a chance to win every dollar that has been stolen by this criminal ring.”¹

Monopoly Comes Back in 2025

After a long hiatus, McDonald’s brought the Monopoly game back to the United States on October 6, 2025, for the first time since 2015.¹⁹ The revived promotion uses both peel-off stickers and digital pieces through the McDonald’s app, with prizes including $1 million in cash, vehicles, vacations, and airline miles. All pieces are now scanned and tracked through the app, and the new version includes independent audits and added security safeguards built around what Jacobson exploited.²⁰

1
CNBC. How the McMillions Scam Rigged the McDonald’s Monopoly Game
2
Los Angeles Times. Jacobson Sentenced in McDonald’s Fraud
3
New York Post. How Ex-Cop Orchestrated $24 Million McDonald’s Monopoly Scam
4
USA Today. McMillions Finale: How McDonald’s Monopoly Game Pieces Were Stolen
5
Oxygen. What Happened to Gennaro Colombo in HBO’s McMillions
6
The Post and Courier. The Time McMillions Scammer Jerry Colombo Said God Told Him to Open Strip Club
7
OCCRP. Ex-Cop Rigged McDonald’s Monopoly to Steal Millions
8
CNN. McDonald’s Indictment
9
The Seattle Times. Million-Dollar Winner Gives Ticket to Charity
10
Los Angeles Times. McMillions HBO Informant Finale Recap
11
Warner Bros. Discovery Press. McMillions Episode 1 Synopsis
12
Oxygen. Where Is FBI Special Agent Doug Mathews From McMillions Now
13
U.S. Department of Justice. Operation Final Answer Press Release
14
U.S. Court of Appeals for the Eleventh Circuit. United States v. Chandler, No. 03-10725
15
Oxygen. What Happened to Jerome Jacobson of McMillions
16
Priceonomics. The McDonald’s Monopoly Fraud
17
NBC News. McDonald’s Game Scam Convictions Erased
18
Express. What Happened to Simon Marketing
19
McDonald’s. Monopoly Returns: More Chances to Win
20
Fortune. McDonald’s Bringing Back Monopoly