Drew Brees

Brees was a 2nd Round pick (#32 overall) by the San Diego Chargers back in 2001, signing a 4 year, $3.6M rookie contract that year. He’d see it out, garnering an $8M franchise tag from the team in 2005 which he opted to play on before hitting free agency for the first time in March of 2006.

The Saints pounced, signing 27-year-old Brees to a 6 year, $60 million free agent contract that included $20M fully guaranteed, and $22M cash in the first year. Once again, Brees would play out the entirety of the contract, which led to yet another franchise tag, this time however - an exclusive rights tender at $16.371M.

New Orleans and Brees negotiated right up to that July extension deadline, before agreeing to terms on a 5 year, $100 million contract that included $40M fully guaranteed, making Brees the first $20M per year player, and the highest average paid player in the history of football. He would play out 4 years, $80M of this deal before beginning a stretch of short, quick contract extensions that refreshed his wallet, and kept his current-year cap hit at bay.

In 2016, Brees turned the $20M remaining on his previous extension into a 2 year, $44M contract through 2017 that paid him $31.25M in the first season. He followed that up with a 2 year, $50M extension through 2019, and a 1 year, $25M contract through 2020 to finish off his career.

In total, Brees signed 7 contracts (2 for San Diego, 5 with the Saints) that secured him over $271M of on-field earnings, which still ranks 8th most in NFL history today.

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Larry Fitzgerald

The Cardinals selected Fitzgerald #3 overall out of Pitt back in 2004, signing him to a 6 year, $52.7M rookie deal (heavily back-loaded with potential escalators). He’d play out 4 years, $20.8M of the deal, before locking in a 3 year, $30M extension with the team through the 2010 season.

In August of 2011 things got real, as a 28-year-old Fitzgerald agreed to a 7 year, $113 million contract extension with Arizona, making him the highest average paid WR ($16.1M) in history, and the 4th highest average paid player in the NFL (behind Brady, Manning, and Manning). He’d play out 4 years of this contract, earning $58.5M over that span, before beginning a trend of short, quick turn-around contracts for cash/cap purposes.

He signed a 2 year, $22M deal in 2015 that became a 1 for $11M contract.
He signed a 1 year, $11M contract in 2016.
He signed a 2 year, $22M contract in 2017.
He signed a 1 year, $11M contract in 2019
And he finished things off with a 1 year, $11.5M contract in 2020.

In total, Fitzgerald signed 8 NFL contracts, all in Arizona, that secured him over $180M of on-field earnings, which ranks 25th most among WRs all-time.

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Luke Kuechly

Selected #9 overall back in 2012 by the Carolina Panthers out of Boston College, Kuechly signed a 4 year, $12.5M rookie contract to join the league. The Panthers had seen enough after three seasons to know they had found a franchise-leading defensive captain, agreeing to a 5 year, $61M extension with the 24-year-old in September of 2015.

Kuechly would see out the next 5 seasons, earning over $53M of the deal, before stepping away from the game due to injury in January of 2020.

He earned over $63M across 8 NFL seasons, signing just two professional contracts along the way.

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Adam Vinatieri

The Patriots signed Vinatieri as an undrafted free agent out of South Dakota State back in 1996, handing him a $1,000 signing bonus on a 2-year minimum deal. It worked out.

Vinatieri followed up a $238,000 tender in 1998 with a 3 year, $2.5M extension in 1999 that included a $900,000 signing bonus, and over $1.2M cash in Year 1. He’d see out the entire deal, adding a 3 year, $5.375M deal in 2002 that made him a Top 3 paid kicker in the league.

Unsure of his future, New England slapped a $2.5M franchise tag on the 33-year-old back in 2005, and Vinatieri agreed to play it out.

He hit free agency for the first time in 2006, joining the Colts on a 5 year, $12 million contract, making him the highest average paid kicker in football at $2.4M. Vinatieri would play the deal out, once again hitting the open market at 39-years-old. The Colts agreed to re-sign him to the tune of  3 years, $9.2M, including a $3.6M signing bonus.

He’d play out that contract in its entirety, agreeing to a 2 year, $5 million extension through 2015 (his age 43 season), following by another 2 year, $6M extension through 2017 (his age 45 season), a 1 year, $3.6M extension through 2018 (age 46) and a final 1 year, $3.8M deal through 2019 (age 47).

In total, Adam Vinatieri signed 11 NFL contracts (5 with New England, 6 with Indianapolis), accounting for over $51M earned on the field across an incredible 24 seasons. He ranks 3rd all-time among career earnings for kickers (Janikowski $53M, Gano, $53M).

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Roger Craig

Craig was the #49 overall pick by the 49ers back in 1983, signing a 3 year, $560,000 contract to join the club that summer. He would platform that into a 5 year, $2.6 million contract in 1986 that took him through the 1989 campaign. Craig would play out another 1 year, $1.5M in San Francisco, before joining the LA Raiders on an $800,000 deal for the 1991 season.

The then 32-year-old would finish off his career in Minnesota, earning $825,000 in 1992, and another $625,000 in 1993.

In total, Craig earned an estimated $7.1M on the field from 1983-1993.

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