1. Max Scherzer (Free Agency)
Back in 2015, the Washington Nationals signed Max Scherzer to a seven-year, $210 million contract during an offseason in which the Yankees badly needed pitching. They had signed Tanaka the year prior, but a partial UCL tear created a ton of uncertainty.
Scherzer was hitting his career stride, too. His previous two seasons before the mega deal saw him win a Cy Young award, lead the AL in wins twice, lead the AL in WHIP, and record at least 240 strikeouts each year. This was the guy. And for $30 million a year? At the time, sure, a bit pricey, but five years down the road? Likely a bargain.
In the end, Scherzer solidified his Hall of Fame case during his tenure with the Nats while the Yankees underachieved because … they had no pitching! They attempted some patchwork moves with Michael Pineda, Nathan Eovaldi, Sonny Gray, Lance Lynn, JA Happ and James Paxton … none of which really worked to varying degrees.
Again, why try and get fancy when you have the resources to spend the money necessary to acquire arguably the best pitcher of this generation? If the Yankees have Scherzer, he pitches the 2015 Wild Card Game and they probably don’t get embarrassed by Houston. Perhaps they make the playoffs in 2016. They likely win the 2017 ALCS. The Red Sox definitely don’t steamroll them in 2018. And we can account for seven games in the 2019 ALCS, at the very least.
We’ll never stop complaining about this failure.