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Crucial Contracts: Sports’ Most Important Free Agent Signings

Crucial Contracts: Sports’ Most Important Free Agent Signings


free agent signings

The moment LeBron James decided to leave Cleveland to play for the Los Angeles Lakers, the entire scope of the coming NBA season changed.

The Lake Show immediately flipped around from a dysfunctional roster that couldn’t make the playoffs for five straight years to a top contender, while the Eastern Conference seemingly crumbled in the blink of an eye.

Across the board in all sports, there have been blockbuster free-agent signings that have made monumental impacts on the players, teams, leagues and even the game itself. Let’s check other athletes whose offseason decisions left an unforgettable footprint.

Peyton Manning, Broncos

Quarterback Peyton Manning was the pride and joy of the Indianapolis Colts in his 13 years with the team.

In his time leading the Colts, Manning racked up a staggering five first team All-Pro selections to go along with four MVP awards.

free agent signings


He brought home the Vince Lombardi Trophy to Indy once, winning Super Bowl XLI, and looked to be a lifer with the Colts after signing a five-year deal with the team in 2011.

Then, everything changed when his neck required a second surgical procedure, leaving him sidelined the entire season and with doubts about his health lingering.

The Colts were terrible without Manning, and their 2-14 record landed them the No. 1 draft pick, which they opted to use on quarterback Andrew Luck, leaving Manning as the odd-man out.

Teams all over the league were salivating over a chance to land Manning, health risk or not. This was, after all, the greatest free agent to land on the market since… well, ever really.

free agent signings

The Denver Broncos hit the jackpot, landing the all-time great. Manning delivered in every way imaginable: Two first team All-Pro selections, three Pro Bowls, one MVP, two Super Bowl appearances and a Super Bowl 50 victory for an unforgettable exit to his final season.

Ironically, while Denver reveled in Manning’s glory, Indy watched in dismay as a season-ending shoulder surgery in 2017 for Luck once again leaves the team’s future uncertain.

Shaquille O’Neal, Lakers

There was never a shred of doubt that Shaquille O’Neal would be a superstar in the NBA. It didn’t even take Shaq one season to acclimate to the talent, as he tore through his rookie season with the Orlando Magic.

free agent signings


By his third season in Orlando, Shaq was an unstoppable force, bullying his way to his first NBA Finals appearance.

Following his fourth season with the Magic, Shaq’s individual and team successes were undeniable, but the Magic continually low-balled their star. The Orlando Sentinel held a poll asking if he was worth paying such a high price for and that was just the tip of the iceberg.

The Los Angeles Lakers had their eyes on the prize all the while, and for every misstep Orlando made, LA took a step in the right direction.

After much negotiation, Shaq signed a seven-year deal worth $120 million that completely changed the NBA landscape.

free agent signings

The Cheat Sheet

Shaq would continue his dominance with the Lakers, earning three straight NBA Finals MVP awards winning three straight championships (2000-02) along with an MVP award (2000) and collection of All-Star selections.

As for the Magic, well, their saving grace came in the form of Dwight Howard, who brought Orlando all of one NBA Finals appearance in 2009.

Alex Rodriguez, Rangers

Alex Rodriguez wasted no time establishing himself as the future of baseball with his first team, the Seattle Mariners. A-Rod was a monster at the plate, repeatedly delivering must-watch performances.

After a playoff push to the ALCS in 2000, the four-time All-Star was officially a free agent, and every MLB team couldn’t wait to get its shot at the megastar.

free agent signings

To say the numbers being thrown around to land A-Rod were “steep” would be the understatement of the century. When the dust finally cleared and the bidding war was over, the Texas Rangers came out the victors.

The price was mind-numbing – $252 million for 10 years.

A 25-year-old A-Rod locked in the deal of the century, and Major League Baseball was NOT happy about it. This moment went way beyond setting a precedent for paying the stars.

The previous MLB high roller was Colorado Rockies pitcher Mike Hampton, who topped out at $121 million for eight years.

free agent signings

This deal dwarfed more than just MLB paydays. The next highest blockbuster deal was paltry in comparison, as the Minnesota Timberwolves held down the fort for the NBA, paying Kevin Garnett $126 million for six years.

To be fair, A-Rod was outstanding in the three years he lasted in Texas before being traded to the Yankees. Then again, the Rangers have only suffered one worse record since the three seasons he played.

Kevin Durant, Warriors

Kevin Durant holds a special place in free agency folklore, not for hitting a monster payday (which he easily could have cashed in on), but for doing the opposite.

When KD hit free agency in 2016, rather than staying in Oklahoma City to continue his legacy with the Thunder or chase a max deal elsewhere, he only had one thing on his mind – winning that ring.

free agent signings

In a decision that stunned the fans, media and entire league, Durant decided to chase a ring with the best team in basketball, the team that had just come back from a 3-1 deficit to defeat Durant and the Thunder in devastating fashion, the Golden State Warriors.

While the decision to join the best team in the league understandably drew criticism from all over, it also served as a trailblazing moment in the NBA and professional sports. The NBA had increasingly been gaining a reputation as a players’ league, meaning the players are taking control of their careers.

free agent signings


The move illustrated that the times of locking in to seemingly lifelong contracts and letting the general managers and owners dictate how one’s career would turn out was over.

He signed a two-year deal with a player option the second year, intentionally taking less money so that the team could fill the roster with the most talent to win a championship… and that’s exactly what he and the Warriors did.

Ilya Kovalchuk, Devils

Originally drafted first overall by the Atlanta Thrashers in the 2001 NHL Draft, left wing Ilya Kovalchuk asserted himself as a dominant scoring threat early on in his career. In his eighth season with the Thrashers, Kovalchuk couldn’t reach an agreement over a contract extension and was traded to the New Jersey Devils.

free agent signings

All About The Jersey

The following year Kovalchuk became an unrestricted free agent and, after fielding numerous offers around the league, decided to re-sign with the Devils.

The over-the-top $102 million deal spanning an NHL-record 17 years seemed downright ridiculous, and the league agreed, forcing a new contract to be drawn up.

The gigantic contract was essentially trying to skirt around the NHL’s salary cap policy. By the end of the end of Kovalchuk’s original monster deal, he would have been 44 years old, collecting a minimal salary to open up a ton of space.

Instead, the NHL rejected the 2010 deal with an added punishment of forcing New Jersey to surrender a third round draft pick in 2011 and a future first round pick along with $3 million.

free agent signings

Yahoo Sports

The NHL and NHLP came to this new agreement:

“In the future, the salary cap hit for any contract that is five years or more in length and takes a player to his 41st birthday or beyond will be determined by the average of the yearly salaries only until the year in which the player turns 40.

All remaining years in the deal after a player turns 41 will be recalculated based on the actual salary of those final years of the contract.”

As for Kovalchuk, he had to settle for a 15-year deal worth $100 million. Tough world we live in.

David Ortiz, Red Sox

Sometimes, it can be the least “newsworthy” events that end up making the biggest impact.

David Ortiz, who had spent the majority of his six seasons with the Minnesota Twins bouncing between the Majors and Minors, was finally getting more playing time and in line for a bump in salary.

free agent signings

In 2002, Ortiz’s final season with the Twins, the slugger was on a one-year deal worth $950,000. Being a small-market team, Minnesota didn’t want to deal with what could potentially be upwards of $2 million to keep him around.

Trade attempts were unsuccessful, so the Twins released him.

The Boston Red Sox jumped at the opportunity, grabbing Big Papi for a cool $1.25 million. One year later, on another one-year deal, Ortiz earned his first of 10 All-Star selections on his way to helping the Sox to their first World Series since 1918.

free agent signings

Big Papi became a Boston fixture, playing 14 years with the Red Sox and winning three World Series with the team, including one World Series MVP award (2013).

It’s hard to find a better example of not squabbling over small sums than all of the greatness Big Papi could have brought Minnesota had the team been willing to stray from such a conservative mindset.

Drew Brees, Saints

It’s often a lose-lose when erring on the side of caution, but it’s hard to blame teams for choosing to take the safe road. The decision the San Diego (RIP) Chargers made in 2005 shows how that can end up being a bitter pill to swallow.

free agent signings


The Chargers drafted Drew Brees in 2001. Brees took over as the starting quarterback by 2002, but struggled heavily the following year. The Chargers were uncertain about their QB of the future, so they drafted Philip Rivers fourth overall in 2004.

Brees had a great 2004 campaign, earning Comeback Player of the Year and followed up with a solid 2005 season until tearing his labrum and damaging his rotator cuff in the final game of the season before hitting free agency.

The Chargers weren’t understandably hesitant to risk spending much on a quarterback with such a serious injury to his throwing arm, offering a heavily incentive-based contract with almost no guarantee.

free agent signings

The Chargers’ loss was the New Orleans Saints’ gain, as they signed Brees to a six-year $60 million deal.

Big risk came with big reward. The Saints ended up landing one of the most dominant offensive forces in NFL history, not to mention championship-winning quarterback, as Brees led the New Orleans to a Super Bowl XLIV victory in 2009.

The Chargers, on the others hand, have topped out at reaching the AFC Championship (2007) with Rivers at the helm.

LeBron James, Heat

Kevin Durant may have been an exclamation mark to state that the NBA is a players’ league, but LeBron James takes the crown for proving this point.

For seven years, LBJ represented his home state playing for the Cleveland Cavaliers, but throughout that time it felt as if he was playing one on five.

free agent signings

James was already such a force that teams had been actively clearing space in the following one, even two seasons leading up to his 2010 free agency.

What ensued was a spectacle unlike any other. ESPN aired an hour long special for the announcement in The Decision.

It was extravagant on every level. Signing a six-year deal for $110 million was an afterthought to everything else. James had effectively assembled a super team, bringing in perennial All-Star Chris Bosh with him to join Dwyane Wade.

Even the way James announced his team remains unforgettable.

free agent signings

Sporting News

“I’m taking my talents to South Beach.”

Just like that, the Miami Heat were the basketball capital of the world, as talent all over the NBA came flocking to get a shot at a title.

It was the King calling the shots the whole way through, and it brought the Heat some shiny championship hardware too.

Barry Bonds, Giants

Will there ever be enough time for it to not be “too soon” to talk about Barry Bonds with Pittsburgh Pirates fans?

The unstoppable (and controversial) force that was Barry Bonds spent the first seven years of his MLB career in Pittsburgh.

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Bonds was named National League MVP in two of his last three seasons with Pittsburgh (1990, 1992) and four straight Gold Glove Awards (1990-94). More importantly to Pirates fans, Bonds played a pivotal role in leading the team to three consecutive NLCS appearances (1990-1992).

Devastating as barely missing the World Series three years in a row was, the ensuing loss far outweighed losing deep in the postseason. The Pirates were unable to compete with big market bids for Bonds, so the super slugger took his talents to San Francisco.


Yahoo Sports

Bonds signed for a then-record $43.75 million six-year deal. While he played out a career littered with individual awards and accomplishments, the Pirates fell into the depths of despair. We’re talking way down in the Pitts.

Bonds only reached one more NLCS and one World Series in his playing career, but after his departure in 1992, Pittsburgh didn’t see the postseason until 2013.

That is two decades without even one playoff appearance.

Reggie White, Packers

The Green Bay Packers have transcended the NFL to become one of the most recognizable teams in professional sports.

With a rich history as one of the oldest franchises in the league and early success winning championships and Super Bowls, it’s easy to forget just how bad the Pack were at one point.

free agent signings

Milwaukee Journal Sentinel

Up until the 1993 season, unrestricted free agency in the NFL was essentially non-existent, as teams were able to hold onto 37 “protected” players, barring those individuals from signing with another team without the old team getting a shot at signing.

Knowing that, it makes much more sense that the Packers were stuck with a perpetually ugly squad that reached the playoffs all of two times from 1968-92.

With the introduction of a truly unrestricted free agency, Green Bay wasn’t going to spare any expense to change the franchise’s misfortunes. The Packers had a young Brett Favre under center on offense, so they bolstered their defense by grabbing the biggest name on the market in defensive end Reggie White.

free agent signings

Milwaukee Journal Sentinel

A six-year deal for $17 million turned out to be the mother of all steals. The Defensive Player of the Year was a sack machine and continued to be just that throughout, helping lead the team to six straight playoff appearances and winning one of their two Super Bowl appearances (1996).

LeBron James, Cavaliers

Without getting into an MJ vs. LeBron argument, there’s no denying that the two are on an equal playing field in what they meant to their respective teams.

While Jordan brought a host of championships to the Bulls, the Cavaliers went from a joke of an organization to having the best player in the league only to go back in shambles upon LBJ’s departure.

free agent signings

When James left Cleveland for Miami, the Cavaliers’ change in fortunes was night and day. Cleveland went from first place in the Eastern Conference (2009-10) to finishing bottom three in three of the four seasons – they also got the No. 1 pick in those years, sheesh – he spent with the Heat.

James, having Ohio roots Cleveland in nearby Akron, decided that it was time to come home and win one for his city. The King ushered in Cleveland’s own Big 3 with lottery pick point guard Kyrie Irving already on the team and Minnesota’s All-Star forward Kevin Love joining.

free agent signings

Heat Zone – The Palm Beach Post

The Cavs’ change in fortunes was instantaneous, as Cleveland went from a lottery pick team with the No. 1 pick to NBA Finalists. The following year, James ended Cleveland’s arduous championship dry spell, winning the 2015-16 NBA Finals.

Fast forward two more years and The King proved he truly is just that, leading the Cavs to four consecutive Finals appearances before closing his second chapter in The Land.

Alexei Yashin, Islanders

One man’s trash is another man’s treasure.

Okay, that might be a little harsh when describing defenseman Zdeno Chara, but when looking back on it, the New York Islanders clearly didn’t think all that much of the giant star defender.

free agent signings

Jim McIsaac / Getty Images

Prior to the 2001-02 season, the perpetually struggling New York Islanders were looking for something drastic to change their fortunes. They decided on trading away Chara, who was still a budding young talent on defense, along with the No. 2 overall pick, goalie Jason Spezza, and Bill Muckalt to get star center Alexei Yashin.

Well, it seemed like Yashin was headed for stardom.

After trading for the restricted free agent, the Islanders looked to lock in their man of the future, signing him to a 10-year deal for a cool $87.5 million. Big mistake.

free agent signings

Jim McIsaac / Getty Images

To be blunt, Yashin’s upside promptly burst in flames and took a downward spiral that blew up in the Islanders’ face. Eventually, things got bad enough that the Islanders bought out Yashin’s contract in 2007, but still took a hit to the salary cap all the way through the 2014-15 season.

At least Chara didn’t go on to have a remarkable career and become a cornerstone of a franchise… too soon, New York?

Catfish Hunter, Yankees

When looking at the numbers, James “Catfish” Hunter signing a five-year contract with the New York Yankees for $3.35 million really doesn’t sound like much at all (shoutout A-Rod).

With context, however, this 1974 deal made Catfish baseball’s first “big money” free agent.

free agent signings

Timothy Hughes Rare Newspapers

When playing with his first team, the Kansas City/Oakland Athletics, Catfish was a monster on the mound. The righty pitcher was unstoppable and was a keystone to the A’s winning three straight World Series titles (1972-74).

The craziest part about Oakland losing its superstar pitcher to New York was that it was owner Charles Finley’s petty action, or lack thereof, that caused it all. A two-year deal worth $200,000 has the stipulation that a $50,000 life insurance annuity had to be paid for Catfish in each of the two years.

Finley refused.

free agent signings

Catfish won his breach of contract dispute and won, making him a free agent. Fast forward to Catfish in Pinstripes, and the Yankees added two more championships (1977, 1978) to the trophy cabinet.

On the microcosm, this deal was still wildly impactful to both teams and the league. On a macro level, this free agent deal kicked off the mega millions we see star MLB players rake in today.

Zdeno Chara, Bruins

Despite his formidable stature, towering above the competition at 6-foot-9, nothing was certain about how his career would pan out. It wasn’t until his seventh NHL season with his second team, the Ottawa Senators, that he earned his first All-Star selection.

free agent signings

Office Chatter

After asserting himself as a top shelf defenseman, Chara entered free agency in 2006 with front offices around the league hoping to pull the talented tough man away from Ottawa.

It didn’t even take 24 hours for 29 teams’ dreams to be dashed.

Teams around the league barely had a chance to come up with a game plan to win Chara over, as the Boston Bruins snatched him up on first day of free agency, agreeing to a $37.5 million deal to lock him in for five years.

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Chara proved to be the perfect leader to take the reins from Bruins captain Joe Thornton, who had recently been traded to the San Jose Sharks.

The big bruiser transformed into a Boston fan favorite, captaining the B’s to two Stanley Cup Finals appearances and winning one (2011) among an array of individual accolades.


Sources: Bleacher Report, Hockey Reference, LA TimesBaseball Reference, Basketball Reference, CBS SportsPro-Football-Reference, Spotrac, Cincy Jungle, New York Times

Below average athlete. Irrationally confident fantasy manager. Competent benchwarmer.

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