Otto Greule Jr/Getty Images

Contract holdouts happen regularly in sports. Money talks like a Charlie Sheen and Chris Tucker flick. In the end, there usually is a winner and loser when it comes to this financial, old Western-style showdowns.

The recent debacle featuring Seattle Seahawks safety Kam Chancellor makes this a timely piece. Looking back over the years, tapping in on all forms of sports, we've selected 20 of the most infamous contract disputes of all time.

To make things a little more interesting, we picked out the winners at the end of the day. Based on production, how each team did and what their long-term value became, the following list was created.

Mitchell Layton/Getty Images

Juwan Howard's emergence from the "Fab Five" program at Michigan gave him rock-star status prior to the 1994 NBA draft.

Instead of inking what was perceived to be a "normal" rookie deal, Howard held out for big dollars. What he got in return was an 11-year, $36 million contract with an opt-out clause after two seasons.

Not only did he make a ton of money early on his career, but the eventual NBA All-Star also bailed from that initial deal and wound up inking a mammoth $100 million dollar endeavor soon after. He was the first player in league history to reach those dollars.

The winner here short and long term was clearly Howard and his agent.

Winner: Juwan Howard

Aubrey Washington/Getty Images

Alexei Yashin tried to beat the system, and instead he suffered the consequences having a binding contract.

The Ottawa Senators captain didn't want to play for the franchise anymore prior to the start of the 1999-2000 season. He was hell-bent on forcing the Senators to allow him to hit free agency, voiding the final year of his deal. Too bad the Senators didn't balk.

Refusing to let Yashin leave set up a back-and-forth exchange consisting of player vs. organization. Yashin held his ground and missed the entire season with the assumption that he would be a free agent afterward.

What really happened was a different outcome. The Senators argued that he didn't actually play for the team, which meant Yashin owed the Senators another year of his services. He would be forced to play for the Senators during the 2000-01 campaign before finally being traded.

The Senators clearly won this holdout, even though Yashin would eventually get himself a sweet paycheck, courtesy of the New York Islanders.

Winner: Ottawa Senators

Elaine Thompson/Associated Press

The most recent NFL holdout involved Seattle Seahawks safety Kam Chancellor.

Chancellor has always been an important member of Seattle's "Legion of Boom" stable. Along with Earl Thomas and Richard Sherman, he helped the Seahawks capture a Super Bowl title two seasons ago.

Looking to join in and get paid like his peers—both Sherman and Thomas received lucrative deals after Chancellor had signed a lesser extension in 2013—he held out. Two weeks into the NFL season, the holdout ended when No. 31 finally returned to the field.

He didn't receive any additional money or a completely reworked deal. It was Andrew Brandt of the MMQB who looked at it from a different point of view:

The common narrative on the Chancellor holdout will be “he caved,” and it is certainly easy to see that on the surface. However, I tend to take the longer view on these things. I would want to know how much of the fine money—I sense it could be all of it—was forgiven and, more importantly, how this contract situation eventually resolves.

For now, we can't pick a clear-cut winner.

Winner: Seattle Seahawks

Eric Bolte-USA TODAY Sports

The Montreal Canadiens extensive history of success stems from a lot of players and coaches. Goalie Ken Dryden is on that Mount Rushmore of winners.

Dryden was a beast. A true warrior who stopped pucks without fear of consequence. And when it came down to it, he was part of what the Canadiens did best: win games.

Before his legendary holdout in 1973, Dryden had already enjoyed a Conn Smythe Trophy as well as two Stanley Cups. He was at the top of his profession, and he wanted to get paid for it.

The Canadiens wouldn't budge, forcing Dryden to sit out the entire 1973-74 season. Eventually he would return to his championship form, get paid and hoist Lord Stanley's Cup four more times.

Winner: Ken Dryden

Erik Perel/Getty Images

Sean Gilbert has an eerie connection to this list. He not only represents an infamous holdout case, but he also happens to be the uncle of New York Jets cornerback Darrelle Revis, per Mike Tanier, who was writing for the New York Times.

Washington slapped Gilbert with the frustrating franchise tag in 1997. Opposed to playing football on that type of deal, he chose to forgo the entire season. By the time '98 came around, the brass in Washington were frustrated. They dealt the defensive tackle to the Carolina Panthers, where he signed a contract worth $46.5 million.

He financially gained from that situation, but his playing career was hampered. Gilbert spent five seasons in Carolina, registering 15.5 sacks and 140 tackles. Turns out he wasn't worth anywhere close to $46.5 million.

Winner: Washington

Robert Houston/Associated Press

One of the first holdouts in baseball history actually came by way of two Hall of Fame pitchers. The craziest part was that it happened at the exact same time.

Don Drysdale and Sandy Koufax were members of the Los Angeles Dodgers way back in 1966. They were at the peak of their respective careers and because of that, they naturally wanted a little more spending money.

This didn't turn out to be a grandiose holdout. Both Drysdale and Koufax didn't miss a single game. But their reasoning for not wanting to suit up was an early indication of how athletes would treat contract negotiations moving forward.

Winners: Don Drysdale and Sandy Koufax

Grant Halverson/Getty Images

Remember when Chris Johnson was the No. 1 pick in fantasy football drafts? The former 2,000-yard rusher had a great thing going with the Tennessee Titans.

Knowing that, Johnson decided that he wanted more money heading into the 2011 season. The holdout lasted until September 1, according to SI.com. That's when the Titans gave Johnson a four-year deal valued at $53.5 million.

It was supposed to keep him under contract until 2016. Obviously that didn't happen. Johnson played in Tennessee until 2013, averaging 4.1 yards per carry in that timespan. His production dipped, and the money increased. Usually that's a losing proposition for the front office.

Winner: Chris Johnson

Craig Melvin/Getty Images

Pavel Bure's contract dispute in 1998 cost the former Vancouver Canucks star his job with the team.

Leading up to the trade that sent him to the Florida Panthers, Bure had a fractured, toxic relationship with the Canucks organization. Tony Gallagher of the Province detailed the ordeal when he was writing for the paper.

Bure's frustration was apparent and because of that there was no hope for reconciliation. He was dealt and wound up in Florida.

It's not easy picking a winner here because Bure was dealt for a wonderful player in Ed Jovanovski. However, the Panthers got a goal scorer, while the Canucks got a centerpiece who wasn't a distraction. In that regard, Bure didn't come out on top.

Winner: Vancouver Canucks

Drew Hallowell/Getty Images

JaMarcus Russell was a colossal, destructive and awful NFL bust. Despite his flaws, the man was also paid a handsome sum of money prior to his rookie season.

After months of holding out, the No. 1 pick in the 2007 NFL draft signed a six-year, $68 million deal. For someone who didn't a play a single NFL down, that type of money was out of the galaxy of reason.

At the time of the incident, Len Pasquarelli—working with ESPN—wrote about the ordeal: "In terms of top overall picks, no one has held out longer than Russell since tailback Bo Jackson declined to sign with Tampa Bay altogether in 1986."

Russell self-destructed and gave Raiders Nation one of the worst career arcs in the franchise's deep history. But the man still got paid like a king. In terms of holdouts and dollars, he walked away victorious.

Winner: JaMarcus Russell

Rob Brown/Getty Images

Eric Dickerson's Hall of Fame career wasn't always filled with roses and smiles. Did you know that he actually held out twice during his outstanding NFL tenure?

The first time was in 1985. Admitting the voodoo-like ways of Reganomics, Dickerson refused to suit up for the Los Angeles Rams until they paid him. Coming off a record-setting 2,105-yard rushing season, the Rams caved and made a deal after he missed the first two games of the year.

Five seasons later, Dickerson held out again. This time he was with the Indianapolis Colts. Once again, he was able to secure a nice sum of money, forcing the team's hand.

Speaking strictly in terms of making money, Dickerson was a champion. He set the bar for future NFL players.

Winner: Eric Dickerson

Stephen Dunn/Getty Images

Philip Rivers has firmly cemented himself as the best quarterback in San Diego Chargers history. In 151 games played, Rivers has thrown for 37,545 yards and 257 touchdowns.

Despite that, he continuously goes overlooked in any conversation surrounding great QBs. It's easy to forget now, but Rivers journey here wasn't easy. On draft day 2004, the New York Giants sent Rivers to the Chargers in exchange for Eli Manning, and before he played a single snap, No. 17 held out for an enticing payday.

John Clayton of ESPN and "ponytail" fame discussed Rivers' contract situation in 2004. Michael Smith, also with ESPN, mentioned a year later that Rivers' decision to hold out until mid-August cost him a starting job, and in the process, it also set Drew Brees up for long-term success.

Eventually, all turned out to be fine. But in the interim and heat of battle, Rivers lost his holdout.

Winner: San Diego Chargers

Associated Press

Joe DiMaggio went to battle with the New York Yankees at a time when baseball players weren't making outrageous salaries.

Still, that didn't matter. He wanted to make more money because, let's be honest, he was an excellent player. By PBS' account, DiMaggio wouldn't budge past the $40,000 salary he desired. The Yankees refused to honor that dollar amount.

They waited it out, and eventually DiMaggio backed off. He signed a deal for $25,000—a fraction of what he had originally asked for.

Winner: New York Yankees

L.M. Otero/Associated Press

Pay the man, Jerry! That was the case when it came to Emmitt Smith and the Dallas Cowboys in 1993.

Smith was the NFL's leading rusher the season before he held out, and to add salt to the contractual wounds, the Cowboys had just won the Super Bowl.

It wasn't shocking that the NFL's top halfback wanted an increase in his wages. You'd think an opulent businessman like Jerry Jones would accommodate those needs. Suffice to say that didn't happen right away.

Smith didn't suit up for the first two weeks of the Cowboys campaign, sending the team to an 0-2 start. Only then did Jones pony up a bit of cash and pay Smith for his services.

Four years and $13.6 million—the highest total for any NFL running back at the time—was the magic number that brought Smith back to Dallas and gave Jones another Super Bowl ring he could display in his office.

Winner: Emmitt Smith

Rocky Widner/Getty Images

Juwan Howard wasn't the only rookie to hold out for more money during the 1994 NBA draft. Glenn Robinson also milked the system with the hopes of securing a sweet deal.

By a New York Times account at the time, Robinson had hopes of making $100 million right out of school. When that didn't happen, he "settled" for a 10-year deal worth $68 million, courtesy of the Milwaukee Bucks. Best part is, the contract was completely guaranteed.

Deals like that today are unheard of. The NBA has nixed that type of leverage for rookies. It worked out beautifully for Robinson. He made a great deal of money and forced the Bucks to meet his demands.

Winner: Glenn Robinson

Julie Jacobson/Associated Press

Darrelle Revis' second run with the New York Jets seems improbable when you remember his epic holdout prior to the 2010 season and the circumstances that followed.

Revis stood his ground for 35 days, demanding more money for his brilliant services. He held on to those feelings before inking a fresh four-year, $46 million deal with Gang Green just before Week 1 of the 2010 season.

The soap opera didn't end there, though. After suffering a knee injury a few seasons later, then-Jets general manager John Idzik sent Revis to Tampa Bay, stunning Jets fans in the process.

All would work out in the end, as Revis wound up earning another inordinate amount of money this past offseason. Rich Cimini of ESPN.com wrote about the particulars, which included $39 million of guaranteed money.

Winner: Darrelle Revis

052042RICHARD DREW/Associated Press

Holdouts don't get much bigger than the Bo Jackson situation that unfolded in 1986.

You have to feel for the Tampa Bay Buccaneers. The story goes that Jackson told the organization they shouldn't waste time drafting him. Of course realizing he was a freakish talent, the franchise pulled the trigger and procured Jackson with the No. 1 overall pick.

Jackson wasn't lying. He bailed on the NFL and instead took his talents to Kansas City to play ball with the Royals. A year later Jackson would re-enter the NFL draft, and the Los Angeles Raiders would attain his services.

Dressed in silver and black, the legend of Bo Jackson would proceed grow into one fitting of mythological creatures.

Winner: Bo Jackson

Focus On Sport/Getty Images

Washington had a bruising tailback in John Riggins. In the late 1970s, Riggins was a force. He controlled Washington's backfield with a vengeance.

After a few stellar seasons, Riggins decided it was time to get paid. He challenged the administration in the nation's capital, hoping they would bail him out.

Too bad that's not what went down. No one batted an eye in Washington, forcing Riggins to sit out the entire season. When he finally returned a year later, he wasn't the same halfback.

According to Michael Fabiano of NFL.com, on his way back "Riggins played in just 23 combined games and failed to rush for more than 750 yards in the following two seasons. In fact, he wouldn't reach the 1,000-yard rushing mark again until the 1983 campaign."

Sometimes holdouts don't always work out the way athletes want them to.

Winner: Washington

Ed Bailey/Associated Press

Mark Messier joining up with the New York Rangers in 1991 was a huge deal. Being an established star already, his departure from the Edmonton Oilers was headline news at the time.

His discontent with Edmonton was the reason a trade was needed. Being smack dab in the middle of a congested New York market, the Rangers jumped at the chance to sign him.

Filip Bondy, writing for the New York Times at that point in his career, analyzed the deal. "No cash was involved. Just faith in a man with the jaw of Arnold Schwarzenegger and the trophy case of Robert DeNiro," he wrote.

The trade turned out to be worth it. Messier helped the Rangers claim a Stanley Cup in 1994. On the other hand, the Oilers haven't won one since he left. You tell me who the winner was.

Winner: Mark Messier

Elsa/Getty Images

The Indianapolis Colts wanted Cornelius Bennett to be an anchor on their defense. They wanted him to change the face of a struggling franchise. All Bennett wanted was to be paid handsomely coming out of Alabama.

The two sides couldn't reach a deal. After 102 days of holding out, per John Clayton of ESPN.com, the Buffalo Bills swooped in and made a deal to acquire the rookie star.

You know what went down shortly after that. The Bills got a stud linebacker and played in four consecutive Super Bowls. For their troubles, the Colts got an all-time great in running back Eric Dickerson.

Winner: Buffalo Bills

Al Bello/Getty Images

Walter Jones and his willingness to hold out became routine in the NFL. The Hall of Fame offensive lineman would repeatedly argue about his worth.

The Seahawks used the franchise tag to keep him at bay, and Jones would miss training camp as a result. It turned out to be an interesting arrangement. Jones made a ton of money by way of the tag before he finally inked a seven-year, $52 million contract in 2005, per John Clayton of ESPN.com.

Picking a winner here is complicated. Jones made a ton of money, while Seattle voided offering him a whopping deal early on. In the end, it was a draw.

Winner: Draw

All stats and information provided by Sports-Reference.com unless noted otherwise.