George Steinbrenner's Greatest Free Agent Signings

I am dead set against free agency. It can ruin baseball. —George Steinbrenner

Yankees owner George Steinbrenner passed away at the age of 80 this week. When one thinks of "The Boss," numerous associations come to mind. Managerial firings, suspensions from baseball, illegal campaign contributions and his Seinfeld caricature.

Yet his lasting legacy will undoubtedly be related to free-agent spending.

In his tenure looking after the Bronx Bombers, Steinbrenner disbursed over $1.8 billion on baseball's best, committed to fielding the best roster only money could buy.

To put that figure in perspective, the nearest team's expenditures are less than half of that monetary sum. More importantly, it's hard to argue the results—New York won seven rings under Steinbrenner's reign.

This got us to thinking: with the copious amounts of cash splashed on free agency, how would Steinbrenner's free-agent armada fare against the best acquisitions from the rest of the Majors?

This process was executed with the following parameters: 1. Players had to be obtained through free-agency. This means no Derek Jeter , Marino Rivera, or Jorge Posada . 2. Players could be taken from any timeframe after signing with their team. This equates to using Barry Bonds ' 2001 season despite being picked up by San Fran in 1993.

If the premise of one team versus the world doesn't appear just, that's because it's probably not and we encourage you to create your own MLB Dream Team Free Agent roster .

Then again, it isn't fair A-Rod makes more than the entire Florida Marlins . Plus, every Yankee used made an All-Star appearance at some point in their respective career, so let's not make this a David v. Goliath affair.

Using our MLB Simulaton engine , we simulated The Boss' Free Agents vs an All-Time FA roster 101 times .

In 1980, Steinbrenner signed Dave Winfield to a 10-year, $23 millon contract making him the highest paid player in baseball.

Prior to the 1977 season, Steinbrenner locked down Mr. October himself, for 5 years and $3 million. The Yankees would go on to win the World Series in 1977 and 1978.

Catfish was Major League Baseball's first multi-million dollar player and first free agent. He inked a deal with the Yankees worth $3.25 million over 5 years.

BENCH: Robin Ventura , Hideki Matsui , Mark Teixeira , Mariano Duncan , Rick Cerone

BULLPEN: Tommy John , C.C. Sabathia , Jimmy Key , Mike Mussina , Phil Niekro , David Wells , Goose Gossage, Mike Stanton , Tom Gordon , AJ Burnett

In November of 2000, Ichiro started a trend by leaving Japan and joining the Seattle Mariners for the cool price of $13 million over 3 years plus the $14 million charge to negotiate with him.

Bonds left the Steel City in 1993 to join the San Francisco Giants for a record free-agent contract of $43.75 million over 6 years.

Greg Maddux was highly coveted after leaving Chicago, but elected to sign with the Atlanta Braves for $28 million over 5 seasons in 1993.

BENCH: Manny Ramirez , Vladimir Guerrero , Ivan Rodriguez , Pete Rose

BULLPEN: Nolan Ryan , Randy Johnson , Jack Morris , Bartolo Colon , Tom Glavine , Rollie Fingers , Randy Myers , Francisco Rodriguez , Billy Wagner , Keith Foulke

Leave it to a guy with an oxymoron for a nickname to help add another to the list.

Although Catfish Hunter did not retrieve jumbo shrimp from the deepest oceans to create one of the tastiest appetizers known to man, he did spark the term "free agency" in the 1970s after escaping Oakland for New York.

Over the next three decades, Yankees' owner George Steinbrenner then took a barrel of gas and doused "free agency" to the point where even the word "free" is demanding a 5-year contract worth $80 million.

With that said, George would be proud to know those he signed managed to hang with the top free agents of all-time. The Boss' free agents won 37-percent of their games against the all-time squad consisting of future (and present) Hall of Famers.

On this day, however, it was the All-Time Free Agent taking Catfish to the fryer early and often.

After a calm first inning, Jim Thome got the hit parade started by blasting a two-run homer to center. The Boss' squad managed to cut the 2-0 deficit in half in the bottom of the 2nd thanks to a Johnny Damon double that scored Reggie Jackson.

The bottom of the third really knocked the Boss' Free Agents on their butt. A-Rod drove in Ichiro, Andre Dawson drove in A-Rod and Thome came through again with a base knock scoring Barry Bonds (who walked 4 times during the game). After three innings, the All-Time Free Agents had jumped out to a 5-1 lead. Hunter surrendered 11 hits in six innings of work.

Meanwhile, Greg Maddux continued to mow down every free agent that stepped into the box. The Atlanta Braves' ace brought the same stuff to the mound that made Bobby Cox grin from ear to ear for seasons in Atlanta. Maddux only allowed one run until the 9th when his pitch count eclipsed 100 pitches.

With one last chance to rally back, trailing 8-1, the Boss' Free Agents scored four runs to make the final score respectable thanks to a RBI single off the bat of Dave Winfield and a three run bomb from Jason Giambi.

But the Boss' Free Agents fall a little short, losing 8-5.

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