Jordan Montgomery, LHP
The Yankees are, shall we say, probably not the star atop Jordan Montgomery's tree? Rumor has it he'd rather reunite with the World Champion Texas Rangers than the Yanks or Cardinals, which makes perfect sense. One of them employs Mike Maddux. One of them is a World Champion.
Sonny Gray, who also won't be returning to New York, has at least experienced a pitching coach regime change since the days when Larry Rothschild told him to quit whining and rely on a pitch he hated. It's all the same group of guys who very recently dismissed Montgomery as a non-playoff starter, told him to lay off his own fastball, and jumpstarted his career with a chemistry-shaking trip out of town.
Should the Yankees pursue Montgomery, who elevated himself to near the top of this free agent class, and will likely be due a contract north of $100 million? Absolutely. Even if his ceiling won't drop your jaw, he's as reliable as they come, and can occasionally spin a gem in a harsh environment, as he recently showed in the ALCS in Houston and road Wild Card series at the Trop. Bob Nightengale, midway through the postseason, theorized that the Yankees would chase the familiar face this winter.
Will Montgomery be interested in the pursuit? He's probably more likely to land deep in the heart of Texas again, though Boston and the Los Angeles Dodgers will also surely come calling.