The Trump Files: How Donald Drove Palm Beach Nuts With an American Flag

Get the Full StoryUntil the election, we're bringing you "The Trump Files," a daily dose of telling episodes, strange but true stories, or curious scenes from the life of GOP nominee Donald Trump.

We all know Donald Trump firmly believes that size matters. It turns out it matters just as much to him when it comes to the American flag.

Trump waged a yearslong battle with the blue bloods of Palm Beach, Florida, the city where his Mar-a-Lago club is located, over everything from his parties to his plans to convert the former mansion to a club and noise from the local airport. Trump launched yet another fight in 2006 when he put up an American flag that smashed the city's flag-flying rules. Palm Beach ordinances allowed for flags up to 4 feet by 6 feet on poles as high as 42 feet; Trump's flag, according to the Sun-Sentinel, was a gargantuan 25 feet by 50 feet on a flagpole 80 feet high.

The city started fining Trump 1,250 a day for flying the flag, but the tycoon was gleeful. "This is a dream to have someone sue me to take down the American flag," he told CNN's Nancy Grace in January 2007. The city did not in fact sue, but Trump predictably did. He filed a 25 million federal suit against Palm Beach, alleging that the city had violated his free speech and equal protection rights in going after his flag. Flying a smaller flag, the suit claimed, "would fail to appropriately express the magnitude of Donald J. Trump's& ;patriotism." Trump also pledged to donate any damages to veterans returning from the war in Iraq.

After what the Sun-Sentinel said were "secret, court-ordered negotiations," Trump and the city struck a deal in April 2007. The city would drop the 120,000 in fines against Trump and allow him to keep the flag on a slightly shorter but still technically illegal 70-foot flagpole. Trump, for his part, would drop the suit and donate 100,000 to a veterans' charity.

According to the Washington Post, Trump wrote to the city a few months later to brag that he'd sent 100,000 to Fisher House, a charity that helps house families visiting hospitalized veterans, and thrown in 25,000 for the American Veterans Disabled for Life Memorial out of the goodness of his heart. But there was still one Trumpian twist to the story. He made the contributions through his foundation a move that was possibly illegal which was primarily funded by other people's money.

Read the rest of "The Trump Files":

Trump Files #1: The Time Andrew Dice Clay Thanked Donald for the Hookers

Trump Files #2: When Donald Tried to Stop Charlie Sheen's Marriage to Brooke Mueller

Trump Files #3: The Brief Life of the "Trump Chateau for the Indigent"

Trump Files #4: Donald Thinks Asbestos Fears Are a Mob Conspiracy

Trump Files #5: Donald's Nuclear Negotiating Fantasy

Trump Files #6: Donald Wants a Powerball for Spies

Trump Files #7: Donald Gets An Allowance

Trump Files #8: The Time He Went Bananas on a Water Cooler

Trump Files #9: The Great Geico Boycott

Trump Files #10: Donald Trump, Tax-Hike Crusader

Trump Files #11: Watch Donald Trump Say He Would Have Done Better as a Black Man

Trump Files #12: Donald Can't Multiply 17 and 6

Trump Files #13: Watch Donald Sing the "Green Acres" Theme Song in Overalls

Trump Files #14: The Time Donald Trump Pulled Over His Limo to Stop a Beating

Trump Files #15: When Donald Wanted to Help the Clintons Buy Their House

Trump Files #16: He Once Forced a Small Business to Pay Him Royalties for Using the Word "Trump"

Trump Files #17: He Dumped Wine on an "Unattractive Reporter"

Trump Files #18: Behold the Hideous Statue He Wanted to Erect In Manhattan

Trump Files #19: When Donald Was "Principal for a Day" and Confronted by a Fifth-Grader

Trump Files #20: In 2012, Trump Begged GOP Presidential Candidates to Be Civil

Trump Files #21: When Donald Couldn't Tell the Difference Between Gorbachev and an Impersonator

Trump Files #22: His Football Team Treated Its Cheerleaders "Like Hookers"

Trump Files #23: Donald Tried to Shut Down a Bike Race Named "Rump"

Trump Files #24: When Donald Called Out Pat Buchanan for Bigotry

Trump Files #25: Donald's Most Ridiculous Appearance on Howard Stern's Show

Trump Files #26: How Donald Tricked New York Into Giving Him His First Huge Deal

Trump Files #27: Donald Told Congress the Reagan Tax Cuts Were Terrible

Trump Files #28: When Donald Destroyed Historic Art to Build Trump Tower

Trump Files #29: Donald Wanted to Build an Insane Castle on Madison Avenue

Trump Files #30: Donald's Near-Death Experience That He Invented

Trump Files #31: When Donald Struck Oil on the Upper West Side

Trump Files #32: When Donald Massacred Trees in the Trump Tower Lobby

Trump Files #33: When Donald Demanded Other People Pay for His Overpriced Quarterback

Trump Files #34: The Time Donald Sued Someone Who Made Fun of Him for 500 Million

Trump Files #35: Donald Tried to Make His Ghostwriter Pay for His Book Party

Trump Files #36: Watch Donald Shave a Man's Head on Television

Trump Files #37: How Donald Helped Make It Harder to Get Football Tickets

Trump Files #38: Donald Was Curious About His Baby Daughter's Breasts

Trump Files #39: When Democrats Courted Donald

Trump Files #40: Watch the Trump Vodka Ad Designed for a Russian Audience

Trump Files #41: Donald's Cologne Smelled of Jamba Juice and Strip Clubs

Trump Files #42: Donald Sued Other People Named Trump for Using Their Own Name

Trump Files #43: Donald Thinks Asbestos Would Have Saved the Twin Towers

Trump Files #44: Why Donald Threw a Fit Over His "Trump Tree" in Central Park

Trump Files #45: Watch Trump Endorse Slim Shady for President

Trump Files #46: The Easiest 13 Cents He Ever Made

Trump Files #47: The Time Donald Burned a Widow's Mortgage

Trump Files #48: Donald's Recurring Sex Dreams

Trump Files #49: Trump's Epic Insult Fight With Ed Koch

Trump Files #50: Donald Has Some Advice for Citizen Kane

Trump Files #51: Donald Once Turned Down a Million-Dollar Bet on "Trump: The Game"

Trump Files #52: When Donald Tried to Shake Down Mike Tyson for 2 Million

Trump Files #53: Donald and Melania's Creepy, Sex-Filled Interview With Howard Stern

Trump Files #54: Donald's Mega-Yacht Wasn't Big Enough For Him

Trump Files #55: When Donald Got in a Fight With Martha Stewart

Trump Files #56: Donald Reenacts an Iconic Scene From Top Gun

Trump Files #57: How Donald Tried to Hide His Legal Troubles to Get His Casino Approved

Trump Files #58: Donald's Wall Street Tower Is Filled With Crooks

Trump Files #59: When Donald Took Revenge by Cutting Off Health Coverage for a Sick Infant

Trump Files #60: Donald Couldn't Name Any of His "Handpicked" Trump U Professors

Trump Files #61: Watch a Clip of the Awful TV Show Trump Wanted to Make About Himself

Trump Files #62: Donald Perfectly Explains Why He Doesn't Have a Presidential Temperament

Trump Files #63: Donald's Petty Revenge on Connie Chung

Trump Files #64: Why Donald Called His 4-Year-Old Son a "Loser"

Trump Files #65: The Time Donald Called Some of His Golf Club Members "Spoiled Rich Jewish Guys"

Trump Files #66: "Always Be Around Unsuccessful People," Donald Recommends

Trump Files #67: Donald Said His Life Was "Shit." Here's Why.

Trump Files #68: Donald Filmed a Music Video. It Didn't Go Well.

Trump Files #69: Donald Claimed "More Indian Blood" Than the Native Americans Competing With His Casinos

Trump Files #70: Donald Has Been Inflating His Net Worth for 40 Years

Trump Files #71: Donald Weighs In on "Ghetto Supastar"

Trump Files #72: The Deadly Powerboat Race Donald Hosted in Atlantic City

Trump Files #73: When Donald Fat-Shamed Miss Universe

Trump Files #74: Yet Another Time Donald Sued Over the Word "Trump"

Trump Files #75: Donald Thinks Exercising Might Kill You

Trump Files #76: Donald's Big Book of Hitler Speeches

Trump Files #77: When Donald Ran Afoul of Ancient Scottish Heraldry Law

Trump Files #78: Donald Accuses a Whiskey Company of Election Fraud

Trump Files #79: When Donald's Anti-Japanese Comments Came Back to Haunt Him

Trump Files #80: The Shady Way Fred Trump Tried to Save His Son's Casino

Trump Files #81: Donald's Creepy Poolside Parties in Florida

Trump Files #82: Donald Gives a Lesson in How Not to Ski With Your Kids

Trump Files #83: Listen to Donald Brag About His Affairs While Pretending to Be Someone Else

Trump Files #84: How Donald Made a Fortune by Dumping His Debt on Other People

Trump Files #85: When Donald Bought a Nightclub From an Infamous Mobster

Trump Files #86: Donald Sues Himself And Wins!

Trump Files #87: Donald's War on His Scottish Neighbors

Trump Files #88: When Donald Had to Prove He Was Not the Son of an Orangutan

Trump Files #89: There Once Was a Horse Named DJ Trump

Trump Files #90: How Donald's Lawyers Dealt With His Constant Lying

Trump Files #91: Donald Flipped Out When an Analyst Correctly Predicted His Casino's Failure

Trump Files #92: Cosmo Once Asked Donald to Pose Nude for 50,000

Trump Files #93: Donald Attacks a Reporter Who Questioned His Claim to Own the Empire State Building

Trump Files #94: When He Had the Hots for Princess Diana and Then Denied It