
Adrian Gonzalez and the 10 Largest Contract Extensions in MLB History
Grin away, Adrian Gonzalez. I would be grinning too if I was making your money.
Adrian Gonzalez just milked the Boston Red Sox for a whopping $154M for a six-year deal. I, for one, can't imagine paying that kind of money for one player. Then again, I'm not trying to beat the New York Yankees year in and year out.
The Yankees and the Red Sox certainly don't mind spending the money. However, other teams have made lucrative deals to keep star players on their payrolls as well.
The following are the 10 most expensive contract extensions in MLB history.
No. 10: Ken Griffey Jr., CIN
1 of 10
In 2000, the Cincinnati Reds made an eight-year deal to retain superstar Ken Griffey Jr., one of the greatest five-tool players to ever play baseball. How much would it cost to keep Griffey in Ohio?
$116.5M over eight years.
No. 9: Ryan Howard, PHI
2 of 10
Ever notice how much these guys smile, even when they are losing?
Ryan Howard hasn't got many reasons not to smile, though. He is on one of the best teams in baseball and has one of the fattest checks in baseball as well.
Howard signed a five-year extension for $125M.
No. 8: Vernon Wells, TOR
3 of 10
In 2008, the Toronto Blue Jays gave Vernon Wells a six-year contract extension for $126M. Vernon apparently ended up not being worth the money to the Jays, who traded him to the Angels.
Maybe the money was in Canadian funds.
No. 7: Johan Santana, NYM
4 of 10
Johan Santana signed a six-year contract extension for $137.5M.
He has also been hurt every year for three years straight.
Wow. If I call in sick to work, they fire me. This guy gets a raise? I'm not saying I can hit his change-up (which is unbelievable), but I do show up to work every day!
Where's my contract extension?!
No. 6: Todd Helton, COL
5 of 10
Why so angry, Todd?
You got an eight-year deal with the Rockies for $141.5M!
Not bad for a guy with a degenerative back condition.
To be fair, Helton is probably one of the most underrated players in MLB. He has always displayed hitting prowess and a Gold Glove or two, or three, to match.
No. 5: Miguel Cabrera, DET
6 of 10
In 2008, Detroit gave Miguel Cabrera a seven-year contract extension for a whopping $152.3M.
I wonder how they come up with these numbers.
Miguel is definitely a good ballplayer but may be the single reason Detroit is in such a rough depression.
No. 4: Adrian Gonzalez, BOS
7 of 10
Adrian Gonzalez signed a seven-year deal for $154M.
And the Sox are in last place in the AL East.
Gonzalez costs nearly as much, per year, as the entire Rays franchise.
He is, however, a bright spot on a team that is proving that you don't always get what you pay for all the time!
No. 3: Troy Tulowitzki, COL
8 of 10
Troy Tulowitzki is the best shortstop in the major leagues. He makes plays that no human being should be able to make. He has fantastic range and fielding ability and makes great plays with absolutely no regard for himself.
Until contract time. Tulowitzki can field like Ozzie Smith but actually has a bat as well. I think he carries it into the negotiation room with him.
The Rockies gave Tulo an eight-year extension for $157.75M.
No. 2: Joe Mauer, MIN
9 of 10
Three batting titles plus three Gold Gloves = HUGE contract extension.
Joe Mauer is the most sought-after player in the bigs. His combination of power and defense makes him one of those catchers that will be in the Hall of Fame at the end of his career.
If the Twins have their way, he will enter the Hall in a Minnesota uniform.
Mauer signed an eight-year, $184M contract with the Twins in 2011, putting him at No. 2 on the list of fattest contract extensions.
Is he worth it? Maybe. We will find out in 2018.
No. 1: Derek Jeter, NYY
10 of 10
Derek Jeter is not the highest-paid player in baseball, but he did have the largest contract extension in history.
In 2001, Jeter signed a nine-year deal with the Yankees for $189M.
The Yankees made sure their franchise face wasn't going anywhere. Was he worth it? To the Yankees, yes. To a smaller ball club, probably not.
The Yankees have had only one world championship in that time frame. The Marlins have had only one as well, and they would have had to get corporate sponsorship from Microsoft to get Jeter in Florida.
The point is this: Yes, these players are great. They really are the best of the best. I am uncertain whether they are so good that they deserve to be paid the GNP of a small country, though.
They are all on good teams, but teams are determined by championships, and none of them has contributed solely to winning one.
I may just be jealous, though. I have decided, at my job, that they pay me just enough not to quit, so I work just hard enough not to get fired. Maybe my bosses should buy a team.
Maybe the Dodgers are on the market...









