The Oldest $100MM Players

Even as massive contracts become more and more common, baseball's first $100MM player remains the oldest person to obtain a nine-figure deal. Kevin Brown signed the first $100MM contract in baseball history after the 1998 season, a year in which the 33-year-old logged 257 innings, struck out 257 opponents and posted a 2.38 ERA. It led to a $105MM guarantee from the Dodgers, the first of its kind in MLB.

It’s been 14 years since Brown finalized his record deal — long enough for teams to hand out 40 more $100MM deals. In the last calendar year alone nine players have signed nine-figure deals. Many have surpassed Brown's $105MM guarantee, but none of them have been older than 33.

Here's the complete, updated list of $100MM players sorted by age, courtesy of MLBTR’s Transaction Tracker (the list includes free agent signings and extensions, but does not include posting fees for Japanese players):

• Kevin Brown, 33, signed a seven-year, $105MM deal on 12/12/1998.
• Alex Rodriguez, 32, signed a ten-year, $275MM deal on 12/13/2007.
• Cliff Lee, 32, signed a five-year, $120MM deal on 12/13/2010.
• Albert Pujols, 31, signed a ten-year, $240MM deal on 12/08/2011.
• Jayson Werth, 31, signed a seven-year, $126MM deal on 12/05/2010.
• Josh Hamilton, 31, signed a five-year, $125MM deal on 12/15/2012.
• Alfonso Soriano, 30, signed an eight-year, $136MM deal on 11/20/2006.
• Ryan Howard, 30, signed a five-year, $125MM extension on 4/26/2010.
• Jason Giambi, 30, signed a seven-year, $120MM deal on 12/18/2001.
• Ken Griffey Jr., 30, signed a nine-year, $116.5MM deal on 2/11/2000.
• Carlos Lee, 30, signed a six-year, $100MM deal on 11/24/2006.
• Zack Greinke, 29, signed a six-year, $147MM deal on 12/09/2012.
• Carl Crawford, 29, signed a seven-year, $142MM deal on 12/8/2010.
• David Wright, 29, signed an eight-year, $138MM deal on 12/04/2012.
• Matt Holliday, 29, signed a seven-year, $120MM deal on 1/7/2010.
• Joey Votto, 28, signed a ten-year, $225MM deal on 04/02/2012.
• Mark Teixeira, 28, signed an eight-year, $180MM deal on 1/6/2009.
• C.C. Sabathia, 28, signed a seven-year, $161MM deal on 12/20/2008 (revised as a 31-year-old on 10/31/2011). 
• Manny Ramirez, 28, signed an eight-year, $160MM deal on 12/19/2000.
• Adrian Gonzalez, 28, signed a seven-year, $154MM deal on 4/15/2011.
• Cole Hamels, 28, signed a six-year, $144MM deal on 07/25/2012.
• Johan Santana, 28, signed a six-year, $137.5MM deal on 2/2/2008.
• Vernon Wells, 28, signed a seven-year, $126MM deal on 12/20/2006.
• Barry Zito, 28, signed a seven-year, $126MM deal on 12/29/2006.
• Mike Hampton, 28, signed an eight-year, $121MM deal on 12/12/2000.
• Jose Reyes, 28, signed a six-year, $106MM deal on 12/04/2011.
• Prince Fielder, 27, signed a nine-year, $214MM deal on 1/24/2012.
• Matt Kemp, 27, signed an eight-year, $160MM deal on 11/14/2011.
• Todd Helton, 27, signed a nine-year, $141.5MM deal on 3/1/2001.
• Carlos Beltran, 27, signed a seven-year, $119MM deal on 1/13/2005.
• Matt Cain, 27, signed a five-year, $112.5MM deal on 04/02/2012.
• Ryan Braun, 27, signed a five-year, $105MM deal on 4/21/2011.
• Ryan Zimmerman, 27, signed a six-year, $100MM deal on 2/26/2012.
• Evan Longoria, 27, signed a six-year, $100MM deal on 11/26/2012.
• Derek Jeter, 26, signed a ten-year, $189MM deal on 2/1/2001.
• Joe Mauer, 26, signed an eight-year, $184MM deal on 3/21/2010.
• Felix Hernandez, 26, signed a seven-year, $175MM deal on 02/07/2013.
• Troy Tulowitzki, 26, signed a six-year, $119MM deal on 11/30/2010.
• Alex Rodriguez, 25, signed a ten-year, $252MM deal on 12/1/2000.
• Miguel Cabrera, 24, signed an eight-year, $152.3MM deal on 3/24/2008.
• Albert Pujols, 24, signed a seven-year, $100MM deal on 2/19/2004.

It's also worth noting that $100MM contracts have been evenly split between extensions and free agent contracts. Since the beginning of the 2009-10 offseason, however there have been 14 $100MM extensions against just nine $100MM free agent signings.