Nathan Eovaldi, Texas Rangers
Nathan Eovaldi circled back to the Yankees this past offseason. He declined a large deal from the Red Sox, then tried to bark up their tree once again after his market cratered a bit. They passed, having already spent money on Kenley Jansen, Chris Martin and Masataka Yoshida.
And so, the Rangers it was for two years and $34 million. At the time, Eovaldi probably thought it would be a neat opportunity to get closer to his Alvin, TX hometown (not Houston close, but still close), all while joining the offseason champions and pitching alongside Jacob deGrom. Little did he know he would become his team's most reliable postseason arm alongside another former Yankee, and would induce one of the most iconic Peter Gammons tweets of all time.
Eovaldi never got to show off his October prowess with the Yankees. He routinely touched 100 with his fastball, but couldn't get it by anyone in pinstripes. His only full year with the team was supremely odd. He helped New York reach the Wild Card Game with 154.1 innings and a 14-3 record, but only struck out 121 men and allowed 175 hits. His 3.42 FIP/4.20 ERA indicated he had room to grow, but it never happened in the Bronx (shocker), as he was sent packing after Tommy John surgery was deemed necessary during a rough 2016.
Since then, he's only become Boston's long relief hero, a hard-earned champion, and the man set to deliver Texas' first title in franchise history. Unless another former Yankee does it instead!