13. Alex Rodriguez

Oh boy…

In February 2004, Alex Rodriguez’s arrival felt more like a major corporate merger than a typical baseball trade. Coming off an MVP season in Texas and carrying a historic contract, Alex Rodriguez moved to New York after Aaron Boone's off-season injury created a third-base opening. This change required a quick adjustment: although Rodriguez had won four straight Gold Gloves at shortstop, he moved to third base to keep Derek Jeter in his usual position.

His early career provided significant regular-season contributions combined with high-stakes October performances. In 2005, he earned his first MVP award while wearing pinstripes, hitting 48 home runs to surpass Joe DiMaggio’s longstanding franchise record for right-handed batters. However, subdued performances in back-to-back ALDS eliminations in 2005 and 2006 fueled a local narrative that his batting struggles intensified under pressure.

Internal tensions reached their peak and then shattered in 2007. Rodriguez had an outstanding season, batting .314 with a league-high 54 home runs and 156 RBIs, earning his second Yankees MVP. However, his on-field success was accompanied by off-field drama; he chose to opt out of his contract during the World Series, sparking tense negotiations that eventually led to a new, even more lucrative ten-year contract to stay with the Yankees.

By 2009, the focus shifted from financial issues to resilience. After major hip surgery and publicly admitting to past performance-enhancing drug use during his Texas years, Rodriguez made a mid-season comeback to lead a revamped team. Come October, he finally quieted postseason critics. He powered the offense through the ALDS and ALCS, hitting five crucial late-inning home runs and driving in important runs in the Fall Classic, earning his only championship ring.

The concluding phase of his pinstripe career became a prolonged battle of attrition. Ongoing injuries hindered his performance, and in 2013, the Biogenesis scandal broke out, leading to a historic 162-game suspension that meant he missed the entire 2014 season. He made a notable comeback with 33 home runs in 2015, but by 2016, age and conflicts with the front office ultimately caught up with him.

As his performance declined and the organization shifted toward a youth movement, the front office arranged his departure in mid-August. He played his last game in pinstripes on August 12, 2016, leaving a legacy of 351 home runs, 1,580 hits, and the memorable 2009 championship banner.

Say what you want about A-Rod, but it can’t be ignored that he was among the best of all time.