Current Republican Presidential challenger Donald Trump is no stranger to the inside of a courtroom. He has been a part of hundreds of lawsuits at every level of the court system, with 169 at the federal level alone (or close to 2.5 per year since his birth).

He has been both a plaintiff and a defendant. He has sued and been sued for both business and personal reasons alike. And he’s both won and lost his share of cases, big and small.

His legal targets have included personal assistants, celebrities, mental patients, people who should probably be mental patients, prisoners, unions, rival businessmen, and his own family members.

In short, there is no lack of legal precedent involving The Donald. To that end, we’ve culled through some of the best of the best for this Top 15 Lawsuits Involving Donald Trump article. Here are our picks!

1. Donald J. Trump vs. Fellow Billionaire Henry Cheng

Donald Trump was the primary plaintiff in a lawsuit against Henry Cheng, a Hong Kong real estate developer who in the 1990s had purchased a 75-acre piece of land along the Hudson River from a then cash-strapped Trump.

According to the New York Times, Cheng’s Hong Kong group was able to buy a $250 million debt on the land for a bargain price of some $90 million, thus taking over the Riverside South area with Trump a presumably begrudging partner.

The word “begrudging” seems appropriate when you consider that Trump had Cheng in litigation until 2009, accusing his fellow billionaire friend of hiding the full books on him, selling properties at $1.8 billion while ignoring higher bids, and tax evasion.

The New York Supreme Court, Appellate Division, handed Trump a final defeat in 2009, ruling that he did not have the right to access all of the defendant’s books and records.

Winner: Cheng

Image Source: HKCHCC.org

2. Donald J. Trump vs. NY Times Reporter Timothy L. O’Brien

Trump took on New York Times reporter and TrumpNation: The Art of Being the Donald author Timothy L. O’Brien when O’Brien had the nerve of accusing “the Donald” of holding a more meager net worth than he liked reporting.

O’Brien’s book (citing three unnamed sources close to Trump) found the real estate mogul and reality TV star with a net worth of between $150 million and $250 million. Trump took exception, according to CNN, finding that the claim hurt his brand.

As a result, he sued O’Brien in 2008 for libel, seeking $5 billion. By the following year, the court had dismissed the case in O’Brien’s favor, per CNN.

Winner: O’Brien

Image Source: Newsweek

3. Donald J. Trump vs. Ex-Wife Ivana Trump

Donald and Ivana Trump appear to have a cordial relationship on the surface, but according to a July 2015 report from the Daily Beast, the former star of The Apprentice sued Ivana for $25 million fresh off the settlement of their 1992 divorce.

Ivana was accused of “‘willful, deliberate and surreptitious disclosure’ of details relating to his finances, despite having signed an agreement that she wouldn’t talk publicly about their relationship,” the Beast reports.

Worse, the news site pointed to a deposition that Ivana gave at the time in which she accused Trump of raping her. She has since clarified she felt “emotionally violated” because of Trump’s cold demeanor toward her, has blasted the implication it was an actual rape, and even endorsed Trump for President.

The primary documents related to their legal jousting are not available to the public, or we would include a link.

Winner: Trump

Image Source: IJ Review

4. Trump vs. Merv Griffin (1988)

For a brief time in 1988, former talk show host Merv Griffin and The Donald went head-to-head over Griffin’s push to break into the Atlantic City, N.J., casino market by purchasing stake in Resorts International.

According to a March 1988 piece from the L.A. Times, Trump controlled “88% of the voting securities of Resorts, largely through Class B stock that he bought for $135 a share” in 1987, and he also served as Company Chairman.

Problems arose when Griffin submitted a high-ball offer of $35 a share for all Class A and B Resorts International stock, which was a substantial boost over The Donald’s then pending bid of $22-per-share. Trump called the Griffin bid “ridiculous.”

Trump then filed a lawsuit, an action Griffin’s reps alleged was done solely in an unsuccessful attempt to intimidate his rival. Trump and Griffin would eventually settle their differences with Griffin getting Resorts and Trump getting a profit the New York Times reported as $400 million.

The Donald was also able to negotiate a future repurchase of the Trump Taj Mahal under the terms of the deal.

Winner: Draw

Image Source: Biography

5. Trump vs Trump

In August 2015, Crain’s New York rehashed a 1984 incident in which Trump sued a developer group for sharing his name.

Jules and Eddie Trump were looking to get into the New York drug store market. Through a case of mistaken identity, industry publication Drug Store News sent a letter of congratulations to Donald J. Trump’s attorney. Naturally, this found its way back to Trump, who was not appreciative of the commonality.

In response, a lawsuit was filed that would linger in court for five years. The Donald’s suit was eventually dismissed, and the other Trumps were denied damages on their countersuit. Jules and Eddie continue to develop properties in Florida and Israel among other locations.

Winner: Jules/Eddie Trump

Image Source: SoFlaNights

6. New York vs. Trump University

Vox’s Libby Nelson gives a detailed rundown of the case against Trump University (aka Trump Entrepreneur Initiative) through March 1, 2016. There are three lawsuits in all, and much of it is still pending, though current developments certainly aren’t favoring The Donald.

New York Attorney General Eric Schneiderman has called it a classic “bait and switch” multi-level marketing scam, and an appeals court recently allowed his $40 million lawsuit against the program to proceed.

Among the allegations: fraudulent marketing claims that Trump himself “hand-picked” all faculty when in reality, he didn’t know many of their names.

Nelson sums up the complaints remarking the following:

“People were lured into a free workshop with marketing materials that promised they’d learn Trump’s real estate secrets from his ‘handpicked’ instructors and maybe even from Trump himself. Instead, they were urged to sign up for a three-day seminar that cost nearly $1,500. And at that seminar, they were pushed to sign up for an elite mentorship program that could cost as much as $35,000 per year.”

Trump remains confident that he will win the lawsuit. Primary source materials related to past judgments can be found through FindLaw both here and here.

Winner: Ongoing

Image Source: CNN

7. William Mays and Louis Buddy Yosha vs. Trump Indiana Incorporated

In the early 1990s, Indiana passed a measure allowing gambling in the state for the first time. A couple of successful area businessmen then sought to partner with Trump Indiana Inc., to open one of the first casinos allowed under the new law. Unfortunately, things went south in a hurry.

Mays and Yosha hoped to lend their support to Trump and cash in on his well-known name. Eventually, they would claim that Trump failed them in two ways: “(1) to make them minority (1 percent each) partners in his Indiana gambling enterprise and (2) to create a foundation-with the two of them on its board of directors and little control from Trump-to benefit various charitable causes in Indiana,” according to the appellate court’s opinion.

Initially, the pair were awarded $1.4 million in damages, but the U.S. Court of Appeals, 7th Circuit, reversed that decision, noting that “Mays and Yosha were essentially seeking millions for almost nothing because for a time they thought they were going to get exactly that, millions for almost nothing.”

The court’s opinion continued: “For lending their names to the Trump team during the license application process, but without actually investing any money or putting any of their assets at risk, Mays and Yosha hoped to hit a jackpot once the casino boat was launched. The desire to put one’s self in that position is completely understandable. But this complicated deal was never reduced to the kind of solid contract that could be comfortably enforced in a court of law.”

The appellate court reversed and remanded the lower court’s decision in favor of Trump.

Winner: Trump

Image Source: Flickr Creative Commons

8. Hakimoglu vs. Trump Taj Mahal

Another one from the early 1990s — this time, Ayhan Hakimoglu sued Trump Taj Mahal for allowing him to continue gambling in spite of his inebriated state, “intentionally and maliciously” enticing him even though they knew he was past the point of coherent, according to the appellate court opinion.

The ABA Journal notes that the Philadelphia-based 3rd Circuit “rejected the argument, saying that New Jersey’s dram shop doctrine did not extend to casinos.”

Winner: Trump

Image Source: Wikimedia Commons

9. Jones vs. Maples/Trump

Charles “Chuck” Jones had a beef with Trump and his then-wife Marla Maples because he felt that Donald shut him out of his rightful place as his wife’s entertainment agent and that he was owed commission from her work.

He brought suit against the couple, but ultimately failed to prove his claims. Jones wasn’t helped by the fact that he’d been arrested in 1992 for breaking into Maples’ apartment and “taking her shoes, underwear, photographs, and private papers, as well as for illegal possession of a weapon,” a court doc from 2002 stated.

Winner: Trump (and Maples)

Image Source: Celebrity Net Worth

10. Holiday Inns, Inc. vs. Donald J. Trump vs. Harrah’s Inc.

In 1985, Holiday Inns, Inc., and subsidiary Harrah’s, went to war with Trump, who counterclaimed “plaintiffs’ breaches of their reciprocal fiduciary duty to him.”

Central to Holiday Inns’ argument was that Trump had breached terms of a partnership deal on Trump Casino Hotel by opening up a competing casino with the Trump name independent of their agreement.

Holiday Inns argued that Trump refused “to recognize plaintiffs’ ownership interest in land designated for a new parking facility and his use of his name in connection with his new casino hotel,” thus creating unfair competition, according to the court document from the U.S. District Court for the District of New Jersey.

The court ultimately denied most of the plaintiff’s case with the exception of the parking facility, on which it gave the parties 45 days to come to terms.

Winner: Trump

Image Source: TripAdvisor

11. Trump International Golf Club vs. Harry Theodoracopulos

In 2012, Trump International Golf Club won its appeal after losing at the lower court to suspended club member Harry Theodoracopulos. Apparently, Theodoracopulos was a “cancer” to the club for certain unbecoming behavior, according to comments allegedly made by Trump himself. The court document notes that his “unbecoming” behavior included abuse of caddies.

Theodoracopulos sought the pro rata share of his membership dues as well as a $200,000 deposit. The appeals court found that the lower court had erred in assuming that Trump International Golf Club had permanently expelled the defendant and predicated their judgment based on that detail.

The court reversed and remanded the decision in the Club’s favor.

Winner: Trump

Image Source: Trump International Golf Club

12. U.S. Dept. of Justice vs. Donald J. Trump

In April 1988, Trump was the target of a civil penalty for his attempts to take over Holiday Corp. and Bally Manufacturing. The Associated Press noted at the time that Trump’s 1986 stock purchases in the two companies “violated the notification procedures required by the Hart-Scott-Rodino Act.”

The law required buyers “to notify the government before purchasing more than $15 million worth of voting stock in a company and wait 30 days before completing the transaction.” As a result of the violations, Trump was forced to pay a $750,000 civil penalty.

The original DOJ complaint can be read in its entirety at this link.

Winner: U.S. Dept. of Justice

Image Source: Wikimedia Commons

13. Trump vs. Palm Beach

This is one of those few Donald Trump lawsuits that stands out, and has been frequently used as a talking point among his supporters. While no official citation is available since Trump ultimately withdrew the lawsuit upon reaching an agreement with the city of Palm Beach, Politico reports that Trump got litigious after violating a piece of code limiting the size of flagpoles when he purchased the Mar-a-Lago Mansion to use as a social club.

He — many say intentionally — violated the code by putting up an 80-foot tall flagpole with an oversized American flag attached. Palm Beach fined him $250 per day every day that the flag was up. The fine swelled to $120,000, and Trump took his case to a national audience saying that the “unpatriotic” Palm Beach community was punishing him for exercising his right to free speech. He would then initiate a lawsuit asking for $25 million in damages. Eventually, he agreed to drop it in exchange for a waiver of the fine.

Here’s where the story gets a little mythic, and can’t quite be confirmed one way or the other. Politico notes that Trump and the city solved their differences in “court-ordered mediation” and that “Trump would file for a permit and be allowed to keep an oversized pole on Mar-a-Lago that was 10-feet shorter than the original pole and on a different spot on his lawn.”

Also as part of the agreement, Trump agreed to pay $100,000 to veterans’ charities. As for that “other part on his lawn,” the unconfirmed part of the story is that he relocated the flag to a man-made hill on the property in order to still get the 80-foot height for which he was hoping.

Winner: Trump

Image Source: Snopes

14. Jill Harth Houraney vs. Donald J. Trump

Jill Harth Houraney once brought a $125 million lawsuit against Trump for alleged sexual assault. Houraney was at the time married to a man named George, who was partnered with Trump on an event called the American Dream Festival.

The year was 1997, and the festival was to be an “event-oriented affair that includes a ‘Calendar Girl’ competition, whereby young, often vulnerable female contestants compete for prizes and titles,” according to Houraney’s 12-page complaint.

The main complaint against Trump was that he groped and violated Houraney’s “physical and mental integrity.” He also engaged in “Svengali-type acts to control and subjugate.” His goal: to turn Houraney into his “sex slave.”

Trump’s representatives vehemently denied there was any truth to the allegations, claiming that Houraney was being used as a pawn in a ploy to get at Trump by her now ex-husband. Oddly enough, Houraney has simultaneously stood by the claims while calling Donald Trump a friend and voicing her support for him in the 2016 election.

Winner: Trump

Image Source: LawNewz

15. Rafael A. Oliveras and Lopez de Victoria vs. National Republican Party and Donald Trump

If you have a PACER account, you can access the full details of this current 2016 attempt to derail Trump’s candidacy through the courts instead of the ballot box. Initiated by Oliveras and de Victoria, LawNewz offers this summary from the plaintiffs:

“Candidate Donald Trump publicly disgraced and discriminated against Hispanics by wholesale comparing them with murderers, rapists and known gang members.”

The plaintiffs’ objective and unlikely outcome: bar Trump from seeking the office of President of the United States “all together.”

Winner (so far): Trump

Image Source: DownTrend

Final Tally: 9 Wins, 4 Losses, 1 Draw, 1 Undecided

So there you have it — Trump’s greatest legal hits and misses as determined by The Reeves Law Group. Any cases deserve to be here, but didn’t make the list? Share your picks in the comments section below!