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By - Sean Jensen

When he woke up in his suburban Chicago home one day in early September, Bears defensive end Jared Allen flipped on ESPN and noticed some NFL news on the ticker.

The Houston Texans had agreed to terms on a six-year, $100 million contract with defensive end J.J. Watt.

“I saw it and thought, ‘This is awesome,’” Allen told Bleacher Report. “All we’ve heard from owners is that the new [collective bargaining agreement] doesn’t allow for these kind of deals anymore. But he’s worked his butt off, and it’s good to see him get rewarded.”

Many agents and executives were curious to see the complete breakdown of Watt’s deal because NFL contracts, unlike NBA and MLB deals, aren’t fully guaranteed and often include creative ways to inflate their stated worth.

There have been more than a dozen $100 million contracts since the Green Bay Packers made Brett Favre the charter member of that club in March 2001.

But virtually all of them are as flimsy as a house of cards and might as well make payouts in Monopoly money.

According to's Jamison Hensley, Pittsburgh Steelers quarterback Ben Roethlisberger last year became the first of the 16 players with a contract worth at least $100 million to earn as much as $70 million of that deal.

The $100 million club, though, appears to be legitimizing as the below infographic illustrates.

The NFL's First 100 Million Dollar Man

On March 1, 2001, Brett Favre signed a "lifetime" contract extension, a 10-year deal worth $100 million with the Green Bay Packers.

Before the popularity of social media, a player and his agent could bask in the glow of a massive deal for a while because contracts took days to be fully processed. Drew Bledsoe signed the second $100 million contract, also in 2001.

“I’ve expressed over and over again my desire to play my entire career with the New England Patriots,” Bledsoe said at the time, according to The New York Times. “It looks like that is a very real possibility.”

Just two games into his 10-year contract, Bledsoe suffered a chest injury and was replaced by Tom Brady, who led the Patriots in 2001 to the first of three Super Bowl wins. Bledsoe was traded to the Buffalo Bills, and he ultimately made $15 million of the $103 million contract.

Initially, the massive contracts were a win-win for clubs and players.

Teams could lock star players into long-term contracts and spread out the signing bonus and other guaranteed monies over many years. Agents could use the headlines for the $100 million deal on websites and in newspapers to land more blue-chip clients.

"Agents wanted those big, fluff deals because it helped in recruiting,” former Chicago Bears general manager Jerry Angelo said. “But it was all perception."

Whereas contracts usually took several days to process, the full terms are now generally available within 24 hours. Players are also savvier about contracts, and clubs are less inclined to sign off on deals with too much funny money.

“Most teams got out of that business with what they call ‘dummy years,’” Angelo said. “Those dummy years potentially created dead money, and it’s the money that’s on your existing cap that keeps you from going out into free agency and doing anything.

“It was a case where you were borrowing from Peter to pay Paul.”

During the 2012 offseason, after he was hired as general manager of the Oakland Raiders, Reggie McKenzie had to clean up the salary-cap mess created by too many imprudent contracts (think quarterback JaMarcus Russell and defensive tackle Tommy Kelly).

The Raiders' salary-cap number was $153 million—$30 million over the enforceable maximum.

“Teams have come to this realization: You can’t mortgage the future to guarantee the present,” Angelo said.

Besides, one current team executive said, “Fluff deals come back to bite you.”

Teams that doctor deals with unlikely-to-be-earned incentives are going to have to rewrite new ones if the player lives up to expectations or cut the cord and move on if he doesn’t.

“With the new CBA, teams are playing it straighter,” the executive said. “Agents too.”

Heading into the 2012 season, the agent for Baltimore Ravens quarterback Joe Flacco wanted to work out a contract extension for his client with the club. But talks weren't substantive, and the two sides decided to let things play out during the season.

“That was really the perfect storm of good things for Joe,” his agent, Joe Linta, said.

Flacco led the Ravens to a 10-6 record and shined in the postseason. He threw 11 touchdowns with no interceptions and won the Super Bowl MVP award.

The key, Linta said, was the fact that he and Flacco were in lockstep on their game plan for the next contract. As a rule, Linta focuses less on the overall value and more on the compensation for the first three years of the deal.

On March 4, 2013, Flacco signed a six-year, $120.6 million contract that included $52 million guaranteed, making him the league’s highest-paid player, even though he’d never played in a Pro Bowl.

Within months, Aaron Rodgers of the Packers and Matt Ryan of the Atlanta Falcons also signed contracts with a combined value of nearly $214 million.

Matt Ryan signed a five-year, $103.8 million contract with the Atlanta Falcons.

Some agents, though, said the momentum toward more bulletproof contracts was set back in June by Colin Kaepernick’s six-year extension with the San Francisco 49ers.

The contract was first trumpeted as being worth up to $126 million with $61 million in “guarantees.”

As the finer points of the deal with the San Francisco 49ers were revealed, however, Kaepernick was actually guaranteed $13 million, per Joel Corry of National Football Post, with the remainder of his contract tied to his health and performance.

In the final analysis, many perceived the contract to be very team-friendly because the 49ers even had Kaepernick pay for a disability policy that would net the club $20 million, if he—the player—suffered a career-ending injury.

Allen pays close attention to player contracts, and he’s alarmed by some of them—and he pins some of that blame on the NFL Players Association.

Matt Ryan signed a 5 year / $103.8 million contract with the Atlanta Falcons.

“When information comes out, what I’m disappointed about is the way our union allows teams to structure deals,” Allen said. “Guys jump at the overall dollar amount. But, in reality, you want to protect yourself for skill, (salary) cap and injury.”

He pointed to the popularity of bonuses tied to players being on the roster on a certain date.

“So now a guy gets punished if he’s injured,” Allen said. “That’s not truly guaranteed.”

The team-friendly nature of the Kaepernick deal is not a surprise given the 49ers' reputation for hard-line negotiating tactics.

For example, they signed Frank Gore to a modest three-year, $21 million contract extension in 2011 and enforced a clause in cornerback Tarell Brown's contract that caused him to forfeit a $2 million escalator clause because he opted to conduct his offseason training at his home in Texas instead of at 49ers headquarters.

The 49ers will be busy working on contracts for key players such as receiver Michael Crabtree, tight end Vernon Davis, defensive end Aldon Smith and guards Michael Iupati and Alex Boone in the near future.

Dez Bryant is potentially next in line for a huge NFL contract.

Crabtree is represented by Eugene Parker, who counts among his clients Deion Sanders, Emmitt Smith, Rod Woodson, Larry Fitzgerald and Walter Jones.

Rarely quoted or interviewed, Parker doesn’t discuss negotiations or contracts after completion. But he’s highly regarded for negotiating strong contracts for his players.

“I’ve never been into fluffing up a deal to make myself look good for headlines,” Parker said. “I look at, ‘What’s in the best interest of the client? What’s fair market value for the client?’

“Whatever those factors are, that’s what I look at to put a deal together, not what’s going to make the contract look good for my benefit.”

In the coming years, he and his agency, Relativity Sports, will handle negotiations for notable NFL players such as Jason Pierre-Paul of the New York Giants, Dez Bryant of the Dallas Cowboys, Alshon Jeffery of the Bears and Crabtree.

Since the new CBA was implemented in 2011, Parker said clubs are more diligent on how and who they're investing in.

“Clubs think they can control a player's rights for seven years. They cost that out,” Parker said. “Seven years can be a career for some players, so that can impact their motivation to give a guy an extension.

“But the superstar players are going to get taken care of regardless.”

Dez Bryant (Top), Jason Pierre-Paul (Middle), and Alshon Jeffery (Bottom) are potentially next in line for huge NFL contracts.

In 2010, Angelo targeted one such player in free agency: Julius Peppers.

The No. 2 pick in the 2002 NFL draft, Peppers had averaged 10 sacks per season for the Carolina Panthers. But Peppers was an unrestricted free agent, and Angelo was determined to get the defensive end. On the opening day of free agency, the Bears signed Peppers to a six-year contract worth $91.5 million, including $42 million guaranteed.

“Anytime you have a chance to get a special player, you do what you have to do to get him. Special is hard to find,” Angelo said. “You rarely find special players come up on the marketplace.”

After trying to trade him this past offseason, the Bears—under the direction of general manager Phil Emery—released Peppers, who earned $52.3 million of his $91.5 million contract before signing a three-year, $30 million contract with the Packers.

That’s what makes Allen an anomaly.

In April 2008, the Minnesota Vikings traded a first- and two third-round picks to the Kansas City Chiefs and then signed Allen to a six-year, $73.2 million contract that made him the league’s highest-paid defensive player. Although other players scored bigger contracts in years to come, Allen distinguished himself in another way after the 2013 season: He became an elite player who earned every penny of his megadeal.

In fact, after triggering some incentives, Allen actually earned $74 million, $31 million of which was guaranteed.

Watt’s six-year, $100 million extension is combined with his original four-year rookie contract, which had $8.8 million remaining, according to the Houston Chronicle. All told, he’s guaranteed $51.876 million, a record for a defensive player.

“For him to actually play it out is incredible,” former Tampa Bay general manager and ESPN analyst Mark Dominik said. “Will J.J. Watt play it out? We need to see the numbers, but he may.”

But Allen says he makes one message clear to other players.

“I tell guys all the time: If you take care of what you need to on the field, the money will take care of itself. If you’re a guy who flashes to get paid, then you’ll steal some extra checks. But that hurts everybody, in the end.”