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Jeremy Lin and 20 Guys Who Got Big Paydays Before They Did Anything

Zack PumerantzAnalyst IIIDecember 7, 2016

Jeremy Lin and 20 Guys Who Got Big Paydays Before They Did Anything

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    It's been made clear that the sports industry is a business—constantly flooded with financial issues, ruthless attorneys and ridiculous settlements.

    But underneath the controversial economics is a bevy of horrific contracts given to athletes and coaches, essentially defining the term undeserved.

    With Jeremy Lin signing a lin-sane contract in Houston after only 35 games (25 starts) of mercurial play, now seems like the time to look at others who signed on the dotted line before truly proving anything.

    Now let's be clear, we're excluding pricey draft picks and international signings, because that could flood a production like this. We're focused on guys who signed at least a year or two into their unspectacular careers.

    Whether these eventual millionaires offered bits of flash and potential or reeked of future success will depend on the choice, but we're positive all were franchise-halting mistakes.

    Here are 20 guys who got big paydays before reaching prosperity.

    Potential is a deadly trait.

20. Matt Cassel, NFL

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    After Patriots poster-child Tom Brady went down with a destroyed knee in Week 1 of the 2008 season, lifetime backup (literally) Matt Cassel finally got his shot. He would become the only quarterback in history to start a NFL game without ever starting in college.

    And during a respectable, albeit limited 15-start run to the playoffs, Cassel would rack up 3,693 yards and 21 touchdowns. But it was essentially his first taste of actual football since his high school days, considering Cassel warmed the pine behind Carson Palmer and Matt Leinart during his Southern California tenure.

    It didn't matter, as he was traded to the Chiefs and signed for six years, $63 million in July of 2009. He's been average-to-solid since, but far from spectacular.

19. Rick DiPietro, NHL

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    This signing seemed more in tune with the Islanders unwilling to admit their 2000 first-overall mistake than a worthless hope for future promise.

    While he'd shown bits of promise during his first few years, it was his signing of the then-second-longest contract in North American sports that had Long Island fans tearing their hair out.

    15 years, $67.5 million. Count that, 15 years.

18. Bryant Reeves, NBA

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    After averaging a modest 13.3 points per game in his rookie season and 16.2 points in 1997, Bryant "Big Country" Reeves was given a six-year, $65 million contract extension. Enormous at that time.

    But the hefty center would eventually crumble under the spotlight and eat his way out of the league. Because of weight-control problems and injuries, Reeves would fall from the NBA scene during the '01-'02 season.

17. Gibril Wilson, NFL

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    In his four years with the Giants, safety Gibril Wilson started 51 of 52 games he appeared in, racking up 360 tackles, six sacks and 11 interceptions. But after winning the Super Bowl, Wilson was offered a six-year, $39 million deal, making him the third-highest paid safety in football behind Troy Polamalu and Bob Sanders (yes, more than future Hall of Famer Ed Reed).

    And the Giants weren't fooled, they let their overpriced, overrated defender take the money and run.

16. Jayson Werth, MLB

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    After a mediocre four-year tenure with both the Blue Jays and Dodgers (two years each), Jayson Werth finally found his niche in Philly, where he totaled 95 home runs and 300 RBI in four years (solid, yet far from elite).

    But naturally, the star-craved Nationals went all in during the 2010 free agency period, signing the gawky outfielder to a seven-year, $146 million contract (13th richest in history).

    A .232 average in his first Washington season didn't exactly silence the doubters.

15. Roy Williams, NFL

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    While he was nothing short of a football God when came out of Texas in 2004, receiver Roy Williams never quite found the production he once scripted as a Longhorn.

    Despite only one good year (2006 in which he recorded 1,310 yards), the unreliable Williams was signed by the Cowboys after being traded from the fed-up Lions.

    Not only did Dallas give up a first-round choice and several other picks in 2009, but they secured the misguided receiver for five years, $45 million ($20 million guaranteed).

    94 receptions over the next three seasons and he was finally cut. He's now in Chi-town with a chance for redemption.

14. Darko Milicic, NBA

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    He's known to some as the Human Victory Cigar, and to others as a complete and utter hardwood bust. But the term potential has trailed '03 second-overall pick Darko Milicic since the day he was chosen one pick after LeBron James and ahead of Carmelo Anthony, Chris Bosh and Dwyane Wade.

    But despite averaging only eight points per game with the Magic during the 2006-07 season, the Serbian mammoth cashed in on a three-year, $21 million contract with the Grizzlies in the offseason.

    Only three seasons later, he was similarly signed by the Timberwolves for four years and $20 million.

    Potential reigns supreme.

13. Joker Phillips, NCAA

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    With succeeding Urban Meyer as wide receivers coach at Notre Dame remaining his career highlight, few expected former Kentucky standout Joker Phillips to make much of a flashy impact.

    But when Rich Brooks was hired as head coach at Kentucky in '02, Phillips decided to trounce back to Wildcat territory and help build a dynasty. 

    After several years of prosperity, Brooks retired and Phillips took over. And despite going 11-14 during his first two seasons as head honcho, Phillips secured a five-year extension worth at least $1.7 million per year.

    Even he seems to be baffled.

12. Aaron Rowand, MLB

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    Any guy willing to run full speed, face first into a wall to save three runs certainly deserves a hefty payday. But five years, $60 million? In the words of Mike Ditka, "C'Mon Man."

    The solid outfielder hit over .300 only once (.309 in his '07 contract year of course), and sure wasn't a franchise-changing high-profile star worth over $10 million per year.

    An unsung hero turned overpaid journeyman for the Giants.

11. Mark Sanchez, NFL

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    A bright future may lie ahead, but Mark Sanchez is the quintessential victim of a team feeling bad that they pursued a better replacement. Picture a guilty boyfriend buying flowers for his girlfriend after flirting with a bartender.

    Who's the bartender you ask? Peyton Manning's tantalizing right arm, which eventually ended up in Denver.

    The three-year, $58.25 million contract may give Sanchez the seventh-highest financial package among NFL quarterbacks, but it doesn't make him more efficient. That's on Marky Mark himself.

10. Jeff Finger, NHL

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    Some called him a top defender in the Western Conference, others said he was the man confused with fellow defenseman Kurt Sauer. Overall, nobody seems to know who Jeff Finger really is.

    But that didn't stop the Maple Leafs from securing the serviceable then-28-year-old defenseman to a prestigious four-year deal worth $3.5 million per season during the free-spending '08 offseason.

    He now finally seems comfortable, in the AHL.

9. Jerome James, NBA

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    Considering Jerome James' career high in points was 5.4 (2002-03 season), we can comfortably call the Isiah Thomas-led Knicks of the mid-2000s victims of the moment.

    Following a mediocre career, James finally found his Supersonic prowess in the 2004-05 playoffs, when he nearly tripled his production in recording 12.5 points and 6.8 rebounds before faltering to the Spurs in the conference finals.

    A five-year, $30 million deal for essentially two playoff series. James would never recover his brief dominance.

8. DeSagana Diop, NBA

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    Despite never averaging more than three points per game in his crumbling career, shot-blocking backup DeSagana Diop was awarded a five-year, $31 million deal from the Mavs, who'd traded him only six months prior.

    Diop now finds himself in Charlotte, where he's started nine games in four years.

7. Brian Cardinal, NBA

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    In his first three seasons, glorified backup Brian Cardinal totaled a paltry 184 minutes, before exploding with 9.6 points and 4.2 rebounds in his fourth season. Somehow that earned him a six-year, $34 million contract from the Memphis Grizzlies (yet again).

    But there's perhaps an intriguing reason behind this signing, just ask Jerry West.

6. Kevin Kolb, NFL

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    After allowing him to marinate on their loaded bench for four seasons, Eagles quarterback Kevin Kolb was finally traded...to the Cardinals, where he instantly hit the jackpot. Five years, $63 million, $21 million guaranteed to be exact.

    All it took was seven Philadelphia starts for the Arizona front office to feel they'd finally acquired their franchise signal caller. Only nine starts last year and it now seems like backup John Skelton may be the better option.

5. Jeremy Lin, NBA

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    All it took was 25 starts for Linsanity to erupt with full force.

    Essentially basketball's version of Tim Tebow, former Knicks sensation Jeremy Lin found himself cashing in with one of the teams that "overlooked his talents" and released him.

    The Rockets were determined to make up for lost time (or jump on the bandwagon), signing Lin for $28.8 million over four years (more than $14 million in the third year).

    In the words of Carmelo Anthony, ridiculous.

4. Derek Dooley, NCAA

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    With the SEC flowing through his gene pool as the son of legendary Georgia coach Vince Dooley, Derek Dooley was seemingly crafted to lead a college football squad to prosperity.

    And after Lane Kiffin royally screwed them, Tennessee could overlook Dooley's 17-20 record as head coach of the Louisiana Tech Bulldogs.

    But a six-year deal worth $1.8 million per year? Let's compare that to his father's starting salary: $12,000 per year.

3. Jim McIlvaine, NBA

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    Coming off a sophomore season in which he averaged a measly 2.3 points, 2.9 rebounds and two blocks per game for the Washington Bullets, 7'1" center Jim McIlvaine was offered a seven-year, $33.6 million contract in hopes he could become a Shaq-stopping defensive force in the paint for the Seattle Supersonics.

    Team chemistry took a major hit following this mind-boggling signing and McIlvaine became exactly what many expected. The same single-digit scoring journeyman he was always destined to be.

2. Darren Dreifort, MLB

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    Despite a record of 39-45 and a flimsy right arm, the Dodgers were sold on Darren Dreifort's future potential. A limited 2001 free-agent market didn't hurt either.

    A five-year, $55 million contract would result.

    Perhaps it was agent Scott Boras' always-manipulative and masterfully-precise handling of the situation. In essence, the man is a legend in the hardball business.

1. Jon Koncak, NBA

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    The fifth pick of the '85 NBA Draft, 7' center Jon Koncak would find himself embracing the chilly bench during his time in Atlanta as a reserve. But that didn't stop the crafty Hawks from presenting Koncak with a six-year, $13 million contract (unheard of for a backup). 

    To be clear, this gave Koncak higher earnings than Michael Jordan, Magic Johnson and Larry Bird.

    Thus the notorious moniker, Jon Contract.

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