Yankees fans have high expectations. Yankees fans don't tolerate players who disrespect their history. Yankees fans seethe when their rivals succeed. But, most of all, Yankees fans are gluttons for punishment.
Admit it. That's why you dig around in threads of Red Sox and Astros fans, hoping to land the perfect insult that finally forces them to show a shred of dignity (you won't find it). That's why you cling to players like Josh Donaldson and Aaron Hicks, sore spots you'd rather ignore, just so you can brag righteously when they come up short yet again.
And that's why you gleefully click lists of the team's worst free agent signings rather than respond to lists of the team's best moves. It's only natural.
Knock on all the wood in the world, but there hasn't been too much movement on this list of horrific decisions over the past few years. The Yankees have mostly shopped at the absolute top of the market or the absolute bottom, and have typically been rewarded.
Still, this franchise's not-so-distant past is littered with awful decisions in free agency, attempted splashes, and -- most of all -- great players who left better situations to come to New York and be overwhelmed. Truly, this experience isn't for everyone.
Also ... doesn't it seem like free agent signings are more likely to turn out poorly than they are to turn out well? A list of the Yankees' best free agent signings of all time would be littered with hyper-cheap deals, uncovered gems and pedigreed veterans fighting for one last title. A list of the worst ones? It's, uh, a lot of players they spent big gobs of money on. So it goes.
For better or worse, here's the punishment you were searching for.
Yankees Worst Free Agent Signings in Franchise History: Who's No. 1 on This List of Disasters?
AJ Burnett's Five-Year, $82.5 Million Deal, 2008-09: Burnett was awful in 2010 and 2011. Like, truly, franchise-history-making-ly awful. He posted the Yankees' highest ERA in a full season ever in 2011 (5.26 ERA, 1.51 WHIP). That said, he was the No. 2 starter on a World Series winner in 2009, something I personally would pay $82.5 million in just one year for. Bad contract, doesn't belong above the honorable mentions.
Randy Winn, 2010: Winn replaced Johnny Damon for only a $1.1 million base salary after the 2009 season, and while that's obviously not a large sum for the 2002 All-Star, it's still hilarious how little he did here. 29 games, 71 plate appearances, .213 average, a single homer ... and a .250 average in 87 games for the Cardinals after being DFA'd.
Kyle Farnsworth's Three-Year, $17 Million Deal, 2005-06: Farnsworth was a harrowing solution to a patchwork bullpen, but at least he pulled it together by the 2008 trade deadline, heading to Detroit in exchange for Ivan "Pudge" Rodriguez. Also, Farnsworth is a professional body builder now, and I would like to stay alive, so I'm giving him the "honorable" stamp.
Aroldis Chapman, Five Years, $86 Million, 2016 (and Three-Year, $48 Million Post-Opt-Out in 2019, Specifically): Don't do it the first time. For SURE don't do it the second time.