4 former Yankees that could return to New York this winter

The New York Yankees still have a number of roster holes entering the 2023 Winter Meetings, many of them of their own making! The more free agency and trade deadline cycles you sit out without acquiring a left fielder of any kind, the more it comes back to bite you. The more Josh Donaldsons you add, while chasing a fan favorite away from third base, the more you yearn for stability two years later. Such is life.

This year's Yankees are stuck between a rock (Brian Cashman's head) and a hard place. Cashman lost his marbles at the GM Meetings, which everyone assumed indicated a rift between he and Hal Steinbrenner ... until Steinbrenner claimed he liked the fire. It was oddly reminiscent of the Seinfeld scene where George Costanza berated the elder Steinbrenner in the hallway ("In the past 20 years, you have caused myself and the city of New York a good deal of distress"), only to be greeted by, "...Hire this man!"

It almost felt like we were set for a Levine/Steinbrenner "Stars! Now!" vs. Cashman "Shrewd moves! Tomorrow!" debate, but both camps might just be aligned instead heading into another prime year for Aaron Judge and Gerrit Cole. Needing to win back a distressed fan base, they could do worse than running it back with a few role players (and one more prominent star) along the way in an effort to build up depth. Rome wasn't built in a day, but the Yankees are officially no longer allowed to rely on the Willie Calhouns of the world. It might work once, but it won't work the other six games that week.

4 former Yankees who could rejoin team in 2023-24 offseason

David Robertson, RHP

Right now, the odds-on favorite to sign David Robertson in free agency is "Some Team That Plans to Trade Him a Few Months Later." Robertson is fresh off the Tour de NL East these past few years, roaming from the Phillies to the Mets (where he was beloved) to the Marlins, a final trade that was viewed as the first sign of Steve Cohen's surrender this past summer. Mets management lost their club, while Robertson lost his fastball; he posted a 5.06 ERA in 22 games in Miami after being good for a 2.05 mark in Flushing.

Someday, the nearly-39-year-old Robertson actually will reach the end of the line, but he had plenty of gas left in the tank during the first half of the 2023 season. One year and $8 million can likely get a deal done, coming off a $10 million contract for the '23 season. No fan would object to the Yankees sniffing around that market, depending on how the rest of the offseason plays out.

Robertson is no longer untouchable, but more often than not, he remains magic.

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.

Gio Urshela, 3B

He's no Josh Donaldson, but he'll do.

The last we heard, Urshela had ditched the crutches after an awful pelvic fracture ended his 2023 season prematurely, but prior to the injury (a complete accident), he was having the same ol' representative season that had come to define his career, post-Yankees breakout. Urshela hit .299 through 214 at-bats, displaying the type of bat-to-ball skills that are often forgotten in the modern game, as well as excellent-looking defense that continues to defy most metrics. He racked up 0.8 bWAR, but had a below-average 91 OPS+ (relatively powerless with just two homers, didn't walk). If the Yankees decided to be the team to help him rehab his image, they could probably expect a slight power uptick, roughly league-average offense, some defensive struggles as he worked to regain the lateral quickness he once had with a reformed pelvis, and off-the-charts intangibles.

Bringing in Urshela on a one-year pact the same offseason Gleyber Torres is most likely to be traded would represent a cruel irony of baseball friendship, but that doesn't mean the Yankees shouldn't consider it. Many of their best times from 2019 to present were fueled by Urshela, and everything got 10 times more hideous the second he left for Minnesota.

Gio Urshela: Starting Shortstop sounded scary during the Carlos Correa/Corey Seager offseason, but the reality following his departure was much more skin-crawling.