Ranking star free agents Brian Cashman passed on by embarrassment level

The Yankees should be ashamed.
Texas Rangers v San Francisco Giants
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The modern era of New York Yankees baseball, as laid out expertly in recent days by CBS Sports' Mike Axisa, has been marked by unnecessary spending cuts, regressions and playoff failures more than it's been dominated by excitement. That's a stark shame, especially after fans were loudly and proudly sold the opening of a window when the "Baby Bombers" arrived in 2017.

Aaron Judge has gone on to become an extended superhuman and captain, but the rest of his cohorts have largely fallen by the wayside. Bad luck's only a part of the puzzle, though, as Brian Cashman, Hal Steinbrenner, and all others involved in building the Yankees' next dynasty instead took the cheap way out nearly every time they were given the opportunity to.

It all began with acquiring Giancarlo Stanton after the 2017-18 season and somehow still managing to slice payroll by $31.2 million. When the Yankees needed to put their foot on the gas pedal, they instead put the car in park.

The team's small-market, cost-cutting maneuvers continued from that point on. Rest assured, Brett Gardner was always taken care of, but somehow, New York couldn't seem to find room for young game-changers when their roster was ready for upgrades. Brian Cashman can't stand the thought of paying for a superstar's later years, but still signed Aaron Judge and Gerrit Cole into eternity and willingly paid for only the later years of Josh Donaldson's contract. Half-measures, half-measures, half-measures ... that's why we're here.

The Yankees have passed on plenty of helpful targets since they last won the World Series in 2009, but in our estimation, these are the most egregious. Apologies to Jon Lester and Cliff Lee.

Ranking Free Agents Yankees Should Never Have Passed On, by Least to Most Egregious