Watch CBS News

10 Most Significant Contracts In New York Sports History

By Daniel Friedman
» More Columns

Eli Manning reportedly wants to be the richest player in football and is looking to negotiate a new contract. While he's a great quarterback, he's not exactly at the top of the NFL totem pole, and so his reported demands are rather nonsensical.

Should he get what he wants, it'd go down as one of the most significant contracts in the history of NY/NJ sports.

Here's a closer look at that list:

10. Eli Manning, Giants (2009)

Eli Manning
Giants quarterback Eli Manning throws a pass during the fourth quarter against the Titans at LP Field on Dec. 7, 2014 in Nashville, Tennessee. (Photo by Wesley Hitt/Getty Images)

You might say we've already seen this movie before. In 2009, Manning signed a six-year, $97.5 million extension that raised his salary over the $100 million mark ($106.9, to be exact). At the time, he became the highest paid player in the NFL, making an average of $15.3 million per year – the highest of any multi-year pact ever signed in the league's history.

9. Pedro Martinez, Mets (2004)

Pedro Martinez
Pedro Martinez with the Mets in 2006 (Photo by Jim McIsaac/Getty Images)

Spoiler alert: Martinez is the only Met on this list. You're probably demanding to know why Bobby Bonilla isn't, and why Jason Bay, David Wright, Carlos Beltran and Johan Santana weren't really candidates for it, either. The reason? This is a discussion about the most significant contracts in NY sports history, not the ten biggest or worst ones. Pedro's four-year, $53 million deal was significant because it marked the beginning of a dramatic roster overhaul. For the first time in years, the Mets started putting a compelling product on the field and really entered a renaissance period from that point forward.

8. Brian Leetch, Rangers (1992)

Atlanta Thrashers v New York Rangers
Brian Leetch (Photo by Chris McGrath/Getty Images)

Coming off his entry-level deal and a Norris Trophy in 1991-92, Leetch signed a seven-year, $19 million contract, making him one of the highest-paid defensemen in the NHL at the time. He was also one of the few players at any position making over $1 million per year. Keeping Leetch in the fold would pay off for both player and team, as he helped the Blueshirts win the Stanley Cup two years into the deal. He would cash in again when that contract expired, getting another big payday from the Rangers in 1999 in order to avoid losing him to free agency.

7. Lawrence Taylor, Giants (1990)

Lawrence Taylor
Lawrence Taylor (Photo credit should read MARK D. PHILLIPS/AFP/Getty Images)

After several successful years, Taylor wanted a hefty raise and it was tough to blame him. He held out of training camp and was eventually given a three-year, $5 million contract, becoming the highest-paid defensive player in the NFL.

6. Derek Jeter, Yankees (2001)

Derek Jeter
The Yankees' Derek Jeter celebrates after a game-winning RBI hit in the ninth inning against the Baltimore Orioles in his last game ever at Yankee Stadium on September 25, 2014. (Photo by Elsa/Getty Images)

By 2001, Jeter had cemented himself as one of the premier players in baseball. The Yankees acknowledged this by inking the face of the franchise to a 10-year, $189 million contract. It was the second-biggest deal in the league at the time, and it was yet another example of the Steinbrenners' willingness to shell out money for a winning baseball team.

5. CC Sabathia, Yankees (2009)

CC Sabathia
The Yankees' CC Sabathia pitches during the first inning against the Cleveland Indians at Progressive Field on Aug. 12, 2015 in Cleveland, Ohio. (Photo by Jason Miller/Getty Images)

As was just mentioned, the Yankees have always been willing to spend big money for big-time talent. What makes Sabathia's seven-year, $161 million contract significant is that, in December 2008 (the month and year he actually signed), it made him the richest pitcher in MLB. That mark has since been surpassed several times by other free-agent hurlers, but seven years ago it was groundbreaking.

 4. Alex Rodriguez, Yankees (2008)

Alex Rodriguez rounds the bases after hitting a solo home run against the Texas Rangers in the top of the sixth inning at Globe Life Park in Arlington on July 27, 2015. (Photo by Tom Pennington/Getty Images)

The Yankees decided they wanted to keep A-Rod aboard for the rest of his MLB career, and gave him a 10-year contract worth $275 million. It was the largest accord in baseball history until it was usurped by Giancarlo Stanton's 13-year, $325 million pact with the Marlins earlier this year. Unfortunately, Rodriguez's tenure in the Bronx has been defined by PED use and controversy. It was a massive investment that should've paid off, but became a disaster for the Yankees and a cautionary tale for other teams thinking about making similar investments.

3. Ilya Kovalchuk, Devils (2010)

Ilya Kovalchuk
Ilya Kovalchuk (Photo by Jim McIsaac/Getty Images)

Kovalchuk's free-agency negotiations highlighted everything that was wrong about the NHL's CBA back in 2010, and it really served as a contextual prelude to the eventual lockout that would occur two years later. His original agreement with the Devils, a 17-year contract worth $102 million, was rejected by the league due to salary-cap circumvention, forcing the Devils and his agent to work out a modified deal. Despite an appeal from the NHLPA, the league's ruling was upheld, further increasing the level of discontent between the league and players' association. Eventually, Kovalchuk worked out a 15-year, $100 million deal with New Jersey, while the organization was slapped with fines and stripped of draft picks as punishment for its circumvention attempt. The best part? Kovalchuk left the Devils a few years later to go play in Russia.

2. Rick DiPietro, Islanders (2006)

Rick DiPietro BIG DL
Rick DiPietro (Photo by Bruce Bennett/Getty Images)

If Kovalchuk's deal was the final knockout blow to massive contract extensions in the NHL, DiPietro's was the one that began the movement. At the time, I remember saying to myself, "there's just no way other teams would ever do something like this." Sure enough, the Philadelphia Flyers handed Mike Richards and Jeff Carter lengthy extensions and, with those, a wave of similar deals followed. It was a trend that never should've started, and it made DiPietro's 15-year, $67.5 million contract look like a bargain compared to some of the other ones that were handed out over the next several years.

1. Joe Namath, Jets (1962)

Joe Namath
Joe Namath (Photo by John Parra/Getty Images for NYCWFF)

Namath's three-year, $427,000 rookie contract was the largest ever given to a first-year player in the history of professional sports. And if the money weren't enough, he was also given a car. It came at a time when both the AFL and NFL were engaged in a bidding war, essentially on a player-for-player basis. It also came at a time when free agency, or the idea of an athlete making contractual demands, was in its infancy. To put it in perspective: Free agency had been around since 1947, but switching teams was widely considered taboo. The first NFL player to actually do so was R.C. Owens, who left the 49ers to go play with the Baltimore Colts in 1962 – just three years before Namath was drafted. The owners of the two franchises would never speak to each other again. Broadway Joe's deal was largely significant, and for a lot of reasons. It was a precursor to the shift in power that was beginning to take place at the negotiation table.

View CBS News In
CBS News App Open
Chrome Safari Continue
Be the first to know
Get browser notifications for breaking news, live events, and exclusive reporting.