Javier Vazquez has the rare distinction of disappointing Yankees fans in two separate stints with the team. The Yankees traded a large package of prospects for him before the 2004 season and promptly gave Vazquez a four-year, $45 million contract. Then, the Yankees traded Vazquez away after one season and he pitched pretty well for five seasons before the Yankees tried again to make him work in a trade with the Braves.
Sadly for the Yankees, Vazquez never figured out how to pitch in New York. Vazquez was legitimately good in the first half of the 2004 season and made the All-Star team, but he cratered in the second half so badly that New York traded him after the season. The entirety of the 2010 season was bad, as he posted a 5.32 ERA in 157.1 innings after finishing fourth in the Cy Young voting with the Braves the year prior. Fool me once, shame on you...
Finally, we come to the most recent entrant to the list in Joey Gallo, and this is another case where it is hard not to wonder what the Yankees were expecting. Sure, Gallo has huge power from the left side that is tempting, considering they play in Yankee Stadium, and he did have a bunch of homers before the Yankees traded with Texas for his services. However, the signs have always been there that Gallo is a recipe for disappointment.
The problem Gallo had, and continues to have, is his hit tool and strikeout totals. After coming over in the trade with the Rangers in 2021, Gallo put up a .160/.303/.404 line, although he did at least hit 13 homers for the Yankees that season. 2022 was worse, as Gallo posted a .621 OPS in 82 games with the Yankees before his time mercifully came to an end when he was moved to the Dodgers. Gallo actually seemed like a decent guy, but Yankees fans were not having it, as he was booed constantly with every fruitless at-bat.