Ranking star free agents Brian Cashman passed on by embarrassment level

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

Michael Brantley, 2018-19 offseason

After 2018, the Yankees needed to get meaningfully better after JD Martinez, Alex Cora and the Red Sox wiped several different floors with them in what was supposed to be Year 1 of their championship window.

Instead, they patched holes with several different mid-tier targets and bullpen additions during an offseason we'll be discussing plenty later on.

By the end of 2019, though, it was clear the one-year wonder Red Sox weren't the team the Yankees should've been worried about. Instead, the Astros weren't going anywhere, and added contact-hitting/reliable Michael Brantley on a two-year, $32 million contract.

Year 2 of that deal ended up being significantly reduced by COVID, but in Year 1, the Yankees went back to the Brett Gardner well instead, using a ridiculous collection of fill-in left fielders as the year continued. Mike Tauchman and Cameron Maybin were very fun! Brantley hit .311 with 22 bombs and an .875 OPS/126 OPS+, knocking the Yankees out of the postseason. New York was an outfielder or two short all year, thanks to injury, while Brantley stayed healthy and mashed. It's not like the Yankees (and the juiced ball) didn't receive production from the position; Tauchman somehow matched Brantley (128 OPS+) in limited duty. But he got hurt and missed the postseason, then turned into a pumpkin in 2020 while Brantley stayed steady. Not the most egregious, but certainly a miss that left New York scrambling and coming up short.

Max Scherzer, 2014-15 offseason

Throwing it back a bit here, but the Yankees found themselves embarrassed into committing to a free agent splurge in 2013-14, following yet another Red Sox title.

That four-man class consisted of Jacoby Ellsbury (holy hell, no!), Brian McCann (predictable regression), Carlos Beltrán (fine, but was inspired to invent Astros' cheating scheme while in New York), and Masahiro Tanaka (beloved No. 3 starter).

If those non-Cano splurges had all worked, the Yankees might not be in need of further reinforcements. But with Tanaka's elbow barking, they had a chance to make it all worthwhile by paying Max Scherzer -- who cost nothing but money -- to really take over the rotation.

The 2015 Yankees somehow made the postseason. scratching and clawing to host (and lose) a Wild Card Game against the Astros. Imagine if they'd matched Scherzer's reasonable deal (seven years, $210 million) in Washington, during which he never finished with a full-season ERA over 3.00 (2020 is fake), won back-to-back Cy Youngs, and finished in the top three two other times?

They didn't, though. They continued to struggle to find a rotation topper until Gerrit Cole arrived. Oops!

Manny Machado, 2018-19 offseason

Noticing a theme here? The year the Yankees really should've gone for it, especially after being kicked in the teeth unexpectedly by the 108-win Red Sox, they instead took another middling step forward financially. They traded prospect depth for James Paxton. They signed Adam Ottavino and extended Zack Britton. They paid JA Happ. They managed to steal DJ LeMahieu (good!), but used the rest of their cash to get out ahead of things and extend Luis Severino and Aaron Hicks unnecessarily (so, so bad!).

And, meanwhile, they let a pair of generational talents wait around all winter, then make exciting new homes elsewhere (we'll get to the other guy by the end of this list).

Those four months in 2019 where fans got to compare Gio Urshela's juiced ball stats to Machado's were fun, but the Padres got an all-timer here, and the Yankees didn't entertain the notion of signing him, even as his value slipped throughout the winter. They were, at one point, considered the favorites for his services. But when you've got Miguel Andújar holding down the position, it's certainly risky to pounce! Whew, boy. Machado paired OPS+ marks of 110, 160, 131, 157 and 113 in San Diego with exceptional defense. The Yankes have Josh Donaldson on the 60-Day IL.

Corey Seager, 2021-22 offseason

The Yankees took a principled stand last offseason during the Winter of Shortstops that they believe in Anthony Volpe. It was admirable. It showed guts. It might pay off by providing the Bombers with a star shortstop on a rookie contract.

But Volpe, even at his best, cannot play two or three positions at the same time, as Gisele famously said about Tom Brady. Corey Seager, a beautiful lefty swinger who won 2020 NLCS/World Series MVP honors, was up for grabs that offseason, replete with concerns that his overgrown frame might not stick at shortstop long-term.

That's great! Sounds awesome! Bummer for other shortstop-needy teams, but not for the Yankees! The Yanks employed both Volpe and Oswald Peraza in the minors, at that point. If they'd signed Seager, they could trade Peraza to fill additional holes, use their newly-acquired talent at short in 2022 (and possibly 2023), then move him off the position once Volpe showed promise. Volpe could even be the starting second baseman in '23 and 2024 while Seager showed him how it was done! Wow. Imagine having a playoff-tested mentor who could slide right over like Cal Ripken Jr. when the time was right?

Nope. Seager went to the Texas Rangers for 10 years and $325 million, a number the Yankees clearly vowed to not even approach. So far, he's still a shortstop, and has racked up 5.3 bWAR, 22 bombs and a .351 average. Calculating for Yankee Stadium's dimensions, that translates roughly to ... carry the three ... 89 homers, a .512 average and the 2022 World Series title. Sadly, once Seager's contract was destined to begin with a "three," you knew the Yankees wouldn't compete, content to roll out the "homegrown talent" portion of the plan only without a powerhouse insurance policy.

Bryce Harper, 2018-19 offseason

Not only did the Yankees pass on Harper, a lifelong Mickey Mantle fan who would've died to bring titles to the Bronx, but they boasted while they did it about how special and unique it made them.

Rest assured, if Harper ever gets the chance to face the Yankees in the World Series (he won't, the Yanks are dead ducks), he will destroy them. He will make Brian Cashman wish he'd never been born, grown hair and lost it.

Harper's free agency will forever be the darkest stain on Cashman/Steinbrenner's resumé. The Yankees' head honcho took a perverse type of bizarre joy in removing himself from the Harper race that winter, stating that New York had "six" outfielders and didn't have any interest in playing the eventual Phillie at first base (something he's doing quite well in 2023, as a matter of fact!).

Counterpoint: Who cares?

Instead of being "predictable" and signing the best player available to a deal that looks like pennies on the dollar these days ($25.38 million AAV, God forbid), the Yankees took the field with their six outfielders, had to acquire six more due to injuries, exiled Giancarlo Stanton to the DH pile, and never hit their ceiling before everything fell apart.

When Stanton fell into Cashman's lap prior to the 2018 season, he should've looked at the move as a prelude to going full Death Star the next offseason and adding Harper, too. Instead, he let it halt his team's progress, then boasted about how disinterested he really was in the future Hall of Famer. Disastrous on a whole 'nother level from the rest of these numbskull calls.