An MLB franchise that has been to the playoffs in 22 of its last 26 seasons with admirable stability in the front office and with its managers shouldn’t be causing sleepless nights for the ownership. But if the ownership isn’t restless with the way general manager Brian Cashman has operated the New York Yankees, then he’s guilty of being asleep at the wheel.

The Yankees just experienced another of their “yeah, but …” seasons by crashing out of the AL Division Series. It was the continuation of woes that Cashman has been unable to resolve even while winning.

Cashman probably survives to run the organization again next year, but 2021 feels like a win-or-else season

The New York Yankees had problems beyond their control

Left-hander James Paxton, a 15-game winner a season ago, only made five starts in the pandemic-shortened 2020 season because of an arm injury. That was five more starts than Luis Severino made following Tommy John surgery in February.

The blow to the New York Yankees was obvious since a healthy Paxton and Severino would have been sturdy reinforcements to the rotation behind $324 million acquisition Gerrit Cole. Coupled with Domingo German going from an 18-game winner in 2019 to a season-long suspension for violating the MLB domestic violence policy, the Yankees ended up with nothing close to their expected rotation.

Those were disruptions that GM Brian Cashman shouldn’t take the hit for, but that doesn’t exonerate him. Cashman, who was bashed by Alex Rodriguez this week,  handcuffed manager Aaron Boone by putting restrictions on J.A. Happ’s innings so that the left-hander didn’t trigger a $17 million option for 2021. He went from a stalwart down the stretch in 2018 to a 1-1 record in nine starts this season.

Brian Cashman has to fix the lineup

Despite what’s annually the highest payroll in baseball, the New York Yankees have a flawed lineup. That’s solely the responsibility of general manager Brian Cashman.

How can a lineup that led the American League in runs scored be flawed? Well, start with the runs the Yankees surrendered in the field.

With the exception of the designated hitter, having your name written into the batting order also implies an obligation to be able to field your position. Catcher Gary Sanchez has never fielded his position adequately, and his batting averages in the past three seasons have been .186, .232, and .147. His 62 home runs can’t mask 27 errors and 30 passed balls. His 41% rate for cutting down attempted steals in 2016 has declined steadily, too.

Middle infielder Gleyber Torres has never looked particularly smooth playing shortstop, but that’s where the Yankees have needed him since bringing DJ LeMahieu aboard as a free agent before the 2019 season. LeMahieu batted .327 last year and then .364 this summer while displaying enough power in his swing to qualify as a corner infielder.

Of course, moving Torres to second base and LeMahieu to third displaces Gio Urshela and leaves the Yankees without a solution at shortstop. Meanwhile, “almost adequate” is about the nicest thing that can be said about the way Luke Voit fields his position at first base.

So, the lineup that looks great at the plate night after night is giving away runs in the field with misplayed balls, throwing errors, and an inability to turn enough double plays. That’s hardly the formula to attract free-agent pitchers who might take an interest in something beyond how many zeros are at the end of their bi-weekly paycheck.

Again, that’s on Cashman and the way he’s built the most expensive roster in baseball.

Here’s how Brian Cashman keeps his job

The New York Yankees last won the World Series in 2009 and haven’t been there since. They’ve been to the postseason for four straight years, so Brian Cashman deserves credit even if he is working without the financial constraints faced by rivals.

However, Cashman has to make moves this offseason if he wants to remain in the role he has held since 1998. And he has to do it at a time when the crosstown New York Mets are expected to start spending big under new ownership. The battle for the back page of the tabloids is a fight that George Steinbrenner never liked losing as an owner.

The easy decision is to let Gary Sanchez go. The pitching staff needs a catcher it can trust to block more than just the occasional throw into the dirt. Replacing him with a .195 hitter who can field the position and call a game constitutes an upgrade.

It’s a tougher call on what to do with second baseman DJ LeMahieu, who just won the AL batting title. LeMahieu, who’ll turn 33 next season, is a free agent who has been making $12 million a year. It might take $85 million over four years to keep LeMahieu, with no assurances over how he’ll play at 36 years old.

However, what Cashman does with LeMahieu determines Gleyber Torres’ future. And, however that plays out, The Athletic points out that the lineup could use another left-handed bat.

The rotation potentially faces an overhaul. The Yankees will let J.A. Happ walk, but James Paxton and Masahiro Tanaka are also free agents. Even with Domingo German returning from suspension, Luis Severino won’t be sufficiently recovered to start the season. So, losing Paxton or Tanaka will require finding a replacement.

Those are just the essentials. Keep in mind it could take more to improve upon a 33-27 record.