Yankees' winners and losers from MLB free agency

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The 2022 New York Yankees season began at an historic pace and ended with an historically embarrassing whimper, as a team that was supposed to challenge the 116-win 2001 Mariners for the regular-season wins record ended up challenging the 116-win 2001 Mariners for "most disappointing postseason."

At least the team didn't enter the free agency cycle with a primary objective that could make or break them for a decade to come -- oh, wait! Aaron Judge, the face of the franchise, nearly leapt to San Francisco (or maybe San Diego) before a last-minute charge from Hal Steinbrenner.

After that was handled, everything came into place quickly -- except a left fielder.

All told, the Yankees brought Judge back and named him captain, and also re-signed his pal Anthony Rizzo to maintain leadership. They imported the most electric left-hander on the market in Carlos Rodón and fortified the bullpen with old friend Tommy Kahnle. Still, somehow, things feel a bit incomplete. Where was the patented Cashman trade? The electric arm buried on someone else's roster? The godforsaken left fielder?!

This offseason has brought mostly wins for the Yankees, but there are still a few losers on the roster.

Winners and Losers From MLB Free Agency: Yankees Edition

WINNER: Oswald Peraza

For the second straight season, the Yankees passed on a shortstop frenzy in free agency to take a chance on their young talent instead.

Last year, the "stopgap" period lasted far too long, and Isiah Kiner-Falefa manned the position solo for nearly the entire season. This year? The shortstop contracts New York passed on were crazier (Xander Bogarts' deal?!), and the internal shortstops were deemed far closer to the show. It's apparently Oswald Peraza's spot to lose in spring training, making him a de facto offseason champion.

LOSER: Aaron Hicks

The spotlight on Aaron Hicks was already glaring in the Bronx at the tail end of last season, growing brighter when he dogged it on a dropped fly ball against the Rays, allowing additional runs to score. However, it seemed like it might dim a bit after his unfortunate ALDS injury, which seemed to officially signal the end to his relevance.

Not so. New York's front office hasn't replaced him, letting Andrew Benintendi walk while hyping up his potential rebound.

You thought Yankee fans had turned on Hicks when he made gaffes down the stretch in 2022? Imagine next Opening Day when he's hailed as the solution in left. The pressure will be crushing.

WINNER: Carlos Rodón (and Gerrit Cole)

Carlos Rodón reportedly desired the pinstripes from Day 1 and charged Scott Boras with getting a deal done. Though it must've been painful for Hal Steinbrenner to extract more cash after getting Aaron Judge's deal done, he managed to nickel-and-dime it to the finish line, making Rodón's dream come true (and giving Gerrit Cole a perfect complement).

The pressure isn't off Cole exactly, but with a fire-breather behind him who embodies everything stubborn fans have accused No. 45 of lacking, the new chain of command should benefit him in 2023.

LOSER: Gleyber Torres

Gleyber Torres struggled in August of 2022, while every other Yankee was struggling tremendously. That's undeniable.

But he posted 4.1 bWAR in 2022 overall with a 114 OPS+. He pounded 7 home runs in May. He OPS'd over .800 in June and July. Somehow, though, he's now become persona non grata and squeezed out of some potential Opening Day lineups in favor of Josh Donaldson?

Now that the Miami Marlins have moved on and acquired Luis Arraez, he's probably safe in the Bronx for Opening Day. But why isn't his role more prominent and assured?

SUPER MEGA WINNER: Aaron Judge

Can't wrap a "Winners/Losers" piece without noting that Judge went from a winking free agent in a San Francisco hotel lobby who'd just suffered through a brutal ALCS to the next Captain of the Yankees who possesses the highest position player AAV in MLB history for the next nine years. Solid glow up for someone who'd already broken the AL single-season home run record.

SNEAKY LOSER: Clarke Schmidt (and OBVIOUS LOSER: Frankie Montas)

A year ago, a fifth starter injury would've sent Clarke Schmidt enthusiastically into the rotation with boatloads of fan support behind him. Now ... everybody's not so sure, and somehow Domingo Germán holds the inside track.

Also ... "Frankie Montas: Fifth Starter" was supposed to represent an embarrassment of riches. Now? It kinda, sorta feels like it represents his ceiling with the Yankees. Does he exist? Is he pitching's Ben Rortvedt?

WINNER: Andrew Benintendi

Coming off a disappointing end to his career in Boston, the former top prospect was resurrected in Kansas City and became the Yankees' first option for "left-handed contact hitting" when they (inevitably) needed an infusion of such things at the 2023 deadline.

Though his Yankees career ended too soon thanks to a wrist snap at the wrong time and a hooked bone flying off its track, Benintendi still managed to beat New York's top offer pretty handily in free agency, signing a five-year pact with the Chicago White Sox that (somehow) ranks as that franchise's largest-ever deal. Good on Benintendi, who found probably two years of extra security in the more comfortable midwest.

LOSERS: Yankees, After the Andrew Benintendi Chase

Not saying the Yankees should've matched Benintendi's contract. Not saying that at all. Five years is an awfully long time for someone who didn't show all that much in the Bronx until about a week before he went down. Spencer Jones is coming. Jasson Dominguez is coming. Aaron Judge is locked down. Harrison Bader maybe should be? Outfield spots aren't plentiful.

That said ... come on. Gotta have a better backup plan than "Telling Everyone Aaron Hicks Will Be Good Again." None of the options were ideal, but not securing any of them still makes the Yankees at worst a loser, and at best a "TBD -- See Me at the Deadline."

Entering the season knowing you have a problem to fix under the gun in July probably isn't a fantastic strategy, though. Whither Daulton Varsho?

WINNER: Brian Cashman

Now he's got Brian Sabean and Omar Minaya around! Both experienced baseball executives should help Cashman immediately with championship-level talent evaluation.

And, in the worst-case scenario, he's gained two shiny new Fall Guys! Win-win.

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