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Adrian Beltre (Third Baseman)

Contracts: 9
Career Earnings: $220M

Signed out of the Dominican Republic by the Dodgers in 1994 for a $23,000 bonus, Adrian Beltre spent the better part of 21 seasons in the majors for LA, Seattle, Boston, & Texas.

He signed a 3 year, $5M pre-arbitration extension in 2000, following his first full season in the bigs that bought out his first run through arbitration. His three year arbitration payout  (2002-2004) totaled just $11M, as it wasn’t until that 2004 season (right before his first run at free agency) that he truly broke out.

Beltre would find a healthy 5 year, $64M free agent contract from the Mariners the following winter, a deal he would play out in its entirety before re-entering the open market in 2010.

The Red Sox would snatch up the 31-year-old on a 1 year, $10M contract that contained a $5M player option in 2011. 50 doubles, 30 homers, and 100+ RBIs later, Beltre would be declining that option, and would cash in on the open market yet again, to the run of 5 years, $80M with the Texas Rangers. Not only did Texas take on an $18M club option in 2016, but they would extend Beltre another 2 years, $36M through the 2018 campaign - the final of his career.

When it was all said and done, Beltre had reeled in over $220M on the field over his illustrious career, a number that ranks him 18th all-time on the total earnings list.

Joe Mauer (Catcher)

Contracts: 4
Career Earnings: $223.275M

Drafted #1 overall back in 2001, Mauer spent all 14 seasons of his MLB career with the Minnesota Twins. He agreed to a $5.15M signing bonus to begin his financial career, filling out two minimum salary seasons in 2005 & 2006 before finding a much heftier pay day.

Prior to the 2007 season, Mauer signed a 4 year, $33M extension with the Twins that would buy out all of his arbitration eligibility. Before entering the final year of that contract, Minnesota re-upped the face of their franchise to the tune of $184M over 8 seasons, placing him financially with another career team captain, Derek Jeter (10 years, $189M for the Yankees).

This massive extension would be Mauer’s last professional contract as 3X batting champ retired after the 2018 season at 35-years-old. He earned over $223M on the field for his efforts, 16th all-time right now, and by far the most ever earned by a catcher (Yadi Molina, $163M).

Todd Helton (1st Baseman)

Contracts: 5
Career Earnings: $164.4M

The #8 overall pick back in 1995 played all 17 seasons of his career as a member of the Colorado Rockies. His financial career began with an $892,500 signing bonus shortly after his draft selection, with his MLB debut coming shortly thereafter (August 2nd, 1997). Helton would play out the 1998 season on a league minimum $190,000, before the Rockies handed him a 4 year, $12M extension to bypass his arbitration eligibility.

Prior to Year 3 of that 4 year extension, Colorado locked in the face of their franchise to a massive 9 year, $141.5M contract, running through the 2011 season. The deal included $13M deferred, the last installment of which was just paid out this past summer.

As he began to age out of his productive ability, Helton & the Rockies agreed to a slight restructure toward the end of the monster contract, converting some of his 2011 salary into signing bonus, while tacking on a 2 year, $9.9M extension to keep him in the fold, but at a more manageable cash/tax salary for the team.

Helton would retire from MLB in October of 2013, having earned over $164M on the field for his efforts.