Following the 2018 season, Bryce Harper and Manny Machado were hitting free agency. Both were perfect All-Star fits for the New York Yankees when considering name recognition, ability to deliver in the clutch, and the need for the Bombers to take their roster over the top after an embarrassing elimination at the hands of the Boston Red Sox in the ALDS.

Instead? The Yankees cut payroll, traded for James Paxton, and maintained that their group of Miguel Andûjar, Clint Frazier, Aaron Hicks and Brett Gardner was enough of a “logjam” to justify passing on two of the most talented players in the game. Eventually, they needed reinforcements anyway, as Gio Urshela and Mike Tauchman ended up having to save the day after injuries/lackluster play.

The Yankees’ choice to remain inactive during one of the best free agent classes of the modern era (before following suit again after the 2021 season!) remains one of the most egregious and arrogant decisions the front office has ever made. Perhaps Hal Steinbrenner played a role in it, but even if that were the case, it’s Brian Cashman’s job to sway the owner when we’re talking about generational talents.

Harper said he never received a call from the Yankees and ended up signing what now looks to be a bargain 13-year, $330 million contract with the Phillies. He’s back in the Bronx for the first time since 2021 and he homered on Saturday, reminding Yankees fans what could have been as they currently deal with unthinkable issues up and down their roster.

The Yankees’ decision to pass on Bryce Harper in 2019 is unforgivable

Harper grew up a Yankees fan. He was a star lefty bat during a time the Yankees’ lineup needed more lefties. He might not have been the most perfect fit in the outfield, but with how the organization has deprioritized defense over the last five years, we’re not sure why that was even an issue for them at the time.

At the very least, if the Yankees were going to sacrifice defense with Harper and Giancarlo Stanton, they could’ve done their best to supplement the rest of the lineup with above-average defenders to make up for it. Just look at the Phillies now, who have managed to fit Harper, Kyle Schwarber and Nick Castellanos into their picture during their run since 2022. The Yankees have gotten into a roster mess and opted for lesser names who play below-average defense anyway. So what’s the excuse now?

What was even more infuriating was the lack of foresight. The Yankees had a poor defensive first baseman in Luke Voit at the position, and Cashman said Harper playing there “wasn’t realistic.” Anybody care to guess what position Harper plays now?

Is he the best defender? No. But that was never his calling card. He can hit for average and power, and he’s a walks machine. He hits to all fields, but that swing was literally built for the short porch (an overused phrase, but it seriously was). He has incredinle postseason numbers (.280 AVG, 1.016 OPS, 17 HR, 34 RBI). He is a monster with runners in scoring position. He was the perfect fit, and would have solved so many roster deficiencies for the Yankees over the past seven years.

Honestly, this was the beginning of the end of the modern day Yankees. And when the book is eventually written, it will be described as the official turning point of Cashman’s tenure in the Bronx going south. Fans can talk all they want about the team making the World Series last year, but they did so with a top-heavy lineup and an incomplete roster, taking down inferior opponents along the way, avoiding all of their chief rivals, and then crumbling at the first sign of superior competition. Had Harper been a part of that, maybe things would’ve changed. We’ll never know, but it certainly feels like some elements would have been different.