To think, the Evan Longoria contract pretty much started this whole thing and was actually criticized at the time. 6 years, $17.5M guaranteed, 3 team options of $7.5M, $11M & $11.5M in his age 28, 29 & 30 seasons ($3M buyout in the first year, so only $14.5M paid for the first 6 years of his career) and the contract was signed after he was held down to start the year, earning the extra year of control so the options covered his last year of ARB and 2 free agent seasons. Probably the most team friendly contract in the history of baseball, Andrew Friedman was just so far ahead of the curve it's incredible, the Shields and Crawford contracts were also absolute steals and those contracts came after they established themselves as major league contributors. 14 years, $44.9M guaranteed + 8 team option years to buy out the primes of 3 of the best players of the late aughts. AND all 3 went on to get big paydays after those contracts expired, $352.6M total guaranteed on their second contracts after turning 30.