What's another word for 'D'oh!'?

Every now and then from our Courtside Seat, we like to play a little word association. Want to play along? Take a look at this list and make note of the first word that pops into your mind as you read each item:

• Gilbert Arenas
• Mark Ingram Sr.
• Mike Leach
• Jayson Williams
• University of Southern California

What are your words?

We'll give you ours at the end of the page. (No fair peeking!) But the truth is, those five -- Arenas, Ingram, Leach, Williams and Southern California -- are redefining some of our favorite adjectives. Facing legal, regulatory and disciplinary challenges, each of them has managed to make a difficult situation worse.

Here's a look at each, along with an assessment of the legal issues and the possibilities. We start with …

A new kind of shootaround

Federal prosecutors are conducting a grand jury investigation in Washington, D.C. An angry David Stern has already levied an indefinite suspension and is threatening to make it worse.

Gilbert Arenas might soon begin to understand he is in real trouble.

The gun laws in the District of Columbia are not quite as strict as the New York City law that put Plaxico Burress in jail for two years, but they could be a real problem for Arenas nonetheless. He transported his guns into the team's locker room at the Verizon Center, allegedly brandished them in a dispute with teammate Javaris Crittenton, and reportedly failed to register them. It could add up to multiple criminal charges. Although in the early days of the police investigation, it appeared that Arenas could avoid incarceration, recent disclosures indicate that this is no longer the case.

On top of the possibility of jail time, Arenas could find himself at the wrong end of a breach-of-contract suit from Wizards ownership. It would be highly unusual and a major challenge, legally, for the organization, but it is not hard to imagine that the Pollin family might use the good-behavior clause in Arenas' $111 million contract in an attempt to kill the agreement and free the team of a major expense and a player who has become worthless to them.

Many other owners have considered such legal actions, but few have pursued the difficult and expensive litigation.

But for a new dimension of "dumb," it is hard to beat Arenas and several teammates acting out a gunfight during a pregame play date in front of fans and photographers. Stern, a brilliant and careful lawyer, knows that issuing punishment before the end of the police process can pose problems for his league, but Arenas so incensed him that he acted quickly and definitively by issuing the indefinite suspension.

A criminal mastermind?

As his son and namesake continues to scale the heights of football fame and fortune (the Heisman Trophy, the most outstanding offensive player award in Thursday night's national championship game), Mark Ingram Sr. sits in a jail in Queens and ponders how long he will be incarcerated. He already faces at least seven years in a federal penitentiary, and on March 5, he will be sentenced to an undetermined amount of additional time because he failed to show up when he was to begin the original sentence. It's difficult to imagine a scenario in which the elder Ingram, a former Michigan State and New York Giants star, will ever make it to an NFL stadium to watch his son, Alabama sophomore running back Mark Ingram Jr., play.

How did the senior Ingram end up in so deep a hole? It began with a phone call March 3, 2000, in which Ingram, according to court documents, bragged to a man he had never met that he could turn counterfeit checks into cash, could produce fraudulent titles for stolen automobiles, and could launder drug money into legal, usable cash.

The phone call was, no surprise, recorded, and the guy on the other end was cooperating with the FBI. Within a few weeks, undercover FBI agents were offering Ingram bogus checks to cash and paying him for stolen cars (a BMW, a Porsche and a Cadillac). All of it was recorded on audio and video tapes, with envelopes of cash in starring roles. The finale came when an undercover agent handed Ingram $100,000 in cash, told him it was drug money, and asked him to transform it into money that could be spent.

Agents watched as Ingram went from bank to bank, depositing less than $10,000 in each account to avoid reports to the IRS. When Ingram was finished, he gave the agent $92,000 in clean and laundered money, and collected a fee of $8,000.

Caught on video, audio and in agent surveillance, Ingram could have entered a quick guilty plea eight or nine years ago and might be finished with his prison time by now. That was not his chosen path. Instead, he delayed and stalled and failed even to appear at numerous court appearances.

On two occasions, he showed up in an emergency room in Flint, Mich., instead of the courtroom in Central Islip, N.Y., where he was supposed to appear. He claimed kidney and heart problems. He offered medical records as an excuse for his failure to appear. But the records, filed in court, showed that he was perfectly normal.

Even when he agreed to plead guilty and was sentenced, he failed to show up to begin the sentence, prompting yet another charge that could easily add two years to his time in prison, according to federal sentencing guidelines.

As he was enjoying his bonanza of cash-generating opportunities, did it not occur to Ingram that things might be going a little too well, a little too easily? Why were things falling into place so quickly and so lucratively?

He now says, "I made mistakes." He's right, of course. He made a staggering string of mistakes. Even more amazing than the breathtaking blunders is the fact that he is still in communication with his son. It may be communication in the form of collect calls, but it is a remarkable demonstration of the love that can exist between a father and a son.

The litigating lion of Lubbock

Congress and the NFL and growing numbers of coaches and team doctors have been publicly worrying about the effects of concussions on football players in recent weeks and months, and yet it appears that Mike Leach might have thought he could still do what coaches were doing to players decades ago. Apparently, if the reports out of Lubbock are correct, he tried to make an example of a player who claimed he had a concussion by accusing him of malingering and by trying to humiliate him. Great idea if it's true, right? A doubly great idea when the player's father, Craig James, is a former NFL and college star and a football analyst at ESPN.

Leach wasn't finished. When Texas Tech, after beginning an investigation, asked him for a simple admission of a mistake and an apology, he refused. Another great idea. And then, when the university suspended him, he filed a lawsuit against the folks who had agreed in February to pay him $12 million over five years. What did he expect? An apology from the university.

To the surprise of no one watching the situation, the university fired him for cause, relying on the James situation and other evidence gathered in the investigation.

Although Leach denies abusing young Adam James and his lawyers insist that they will win their lawsuit, he is now left with a thin to nonexistent claim for contractual damages. Leach began the season as a hero in Lubbock. With only a few more winning seasons, Red Raiders fans would have been planning a statue of coach Leach to erect next to the giant statue of Buddy Holly already featured in downtown Lubbock.

By misreading the legal situation, the coach who was building a legend has become a claimant trying to build a case for damages.

A continuing fall

Blessed with good lawyers, a wife who stood by him, and a forgiving jury, former NBA star Jayson Williams managed to avoid prison time for seven years after the fatal shooting of his limo driver and a failed cover-up in his New Jersey mansion.

But in an escalating series of disasters, his lawyers will be in court Monday to ask for leave to end their representation of Williams, his wife has filed for divorce, and his mansion is gone. Williams was shot with a Taser by police in a bizarre episode in a New York hotel room in April, was arrested in a bar fight in North Carolina in May, and is now charged with DWI after apparently driving his Mercedes SUV into a barrier in New York at 3:15 a.m. on Tuesday of this week.

And that isn't all. Williams claimed in a court appearance that he is "flat broke"; broke down in tears in another court appearance; and is, according to court papers, more than $200,000 behind in child support.

His luck in the case of the death of the limo driver is also running out. He might soon face a prison term. He has been awaiting a retrial on the reckless-manslaughter charge, but according to an AP report, he might have already agreed to a plea bargain to serve between 18 months and three years. (The uncertainty is connected to the withdrawal of the lawyers.)

It's a sad fall for an NBA star who looked to be well on his way to a lucrative post-playing career as a broadcaster.

Investigations, violations and litigation

Amid O.J. Mayo problems and Reggie Bush allegations, it is easy to see why USC athletic director Mike Garrett is maintaining a low profile. Bush left Southern California four years ago and Mayo left two years ago, but their toxic legacies live on.

Garrett is the guy who must respond to the various problems and try to minimize the penalties and sanctions that could be coming. But claiming that he cannot comment on "ongoing investigations," he is not doing news conferences. He is not returning phone calls. His only availability is in prerecorded messages on a Trojans Web site.

Garrett's refusals to answer questions or provide detailed responses to the allegations leads to more and more rumors and speculation, none of it supporting USC. If he were to address the issues in a forthright way, he might begin to lead the athletic department back to some level of respectability.

In a clumsy attempt to minimize the impact of school-imposed sanctions resulting from cash payments made in the recruiting of Mayo, Garrett chose to put a recorded statement up on the Web site at a time that coincided perfectly with the NFL's busy schedule of regular-season-ending games last Sunday.

Although the Mayo infractions were first reported by ESPN's Kelly Naqi in May of 2008 (see her "Outside the Lines" story here, Garrett has yet to address the situation in any detail.

His conduct leaves a great institution of higher learning in an embarrassing position, with current players and coaches paying the price for earlier problems.

It's hard to imagine how Garrett or anyone else at USC thinks this approach is a good idea.

Word association, redux

So here's that list again. And this time, the applicable adjectives -- the ones we came up with -- are attached.

• Gilbert Arenas: dumb
• Mark Ingram Sr.: dumber
• Mike Leach: foolish
• Jayson Williams: sad
• University of Southern California: pathetic

Lester Munson, a Chicago lawyer and journalist who reports on investigative and legal issues in the sports industry, is a senior writer for ESPN.com.