Brian Cashman
(Photo by Michael Reaves/Getty Images)

The New York Yankees have to shake off another early playoff exit and start thinking of how to build a better team for 2021.

The New York Yankees are officially in their offseason, and it’s time to get back to work.

General manager Brian Cashman’s plan was easy last season. Gerrit Cole was the biggest name on the market and the Yankees needed pitching. Signing the right-handed ace to a $324 million contract wasn’t just great news, but practically prophetic. Once he was signed, New York could basically kill time until spring training.

However, this winter will be the exact opposite. The Yankees likely won’t be active buyers in the free-agent market. Most of the positions are spoken for. Even though New York underachieved in this abbreviated season, the Yankees’ core is quite strong and should be for the foreseeable future.

But questions still remain. How will the Yankees address their own free agents? What’s the pitching staff going to look like? What on earth happened in 2020, and what can be done to prevent 20-game slumps in the future?

Thankfully, Cashman and manager Aaron Boone are often on the same page. By sticking to the following plan, 2021 should be a better year for the New York Yankees.

Re-sign key free agents

This almost goes without saying. The Yankees must re-sign two impending free agents in right-handed pitcher Masahiro Tanaka and infielder DJ LeMahieu.

The reasoning behind this is simple. LeMahieu is the reigning American League batting champion and an elite fielder. 2020 was only his second year with the Yankees, but he had a career season in 2019 when he hit a career-high 26 home runs with 102 RBIs. Moreover, as Bryan Hoch of reported last month, it sounds like LeMahieu wants to stay in the Bronx.

Similarly, the Yankees need to equally prioritize re-signing Tanaka. He’s been in pinstripes his entire MLB career and, this year aside, has a reputation as a playoff legend. The good news is in the Division Series against the Tampa Rays, it seems he was tipping pitches and that should be fixed easily.

On the whole, Tanaka has pitched to a 3.74 ERA as a Yankee and is a vital member of the starting rotation. He’s not a spring chicken and turns 32 next month but, like his teammate LeMahieu, is very reliable. Plus, remember he opted in for three remaining years on his deal after 2017 instead of testing the market.

In terms of money, LeMahieu made $12 million a year as a Yankee over the course of two seasons. Tanaka just finished a seven-year, $150 million deal. If Cashman can tack on an extra year to whatever both men are seeking, a hometown discount should be in the cards.

Address the pitching rotation

The New York Yankees also have a lot of decisions to make regarding next year’s starting rotation. The only surefire locks are Cole, Jordan Montgomery, and likely the youngster Deivi Garcia. Given how Tanaka loves playing in New York and has said as such, we’ll assume he re-signs with the team for argument’s sake.

This leaves one giant hole at the back end and a tough decision for Cashman. Part of the problem can be solved by letting certain free agents walk. Veteran lefty J.A. Happ turns 38 Monday and shouldn’t return. James Paxton is a good pitcher, yet is injured way too often and shouldn’t come back on a long-term deal.

This is where the Yankees have some options. Clarke Schmidt is a highly-touted pitching prospect, but struggled to a 7.11 ERA. Michael King has potential, but posted a 7.76 ERA in nine games (four starts) and, along with Schmidt, still has a lot to learn. Both can learn a life lesson from Kermit the Frog because for young pitchers, it’s not easy being green.

Then, there’s Domingo German, who missed all of 2020 as he served a domestic violence suspension. He’s certainly an option for 2021, but both Cashman and owner Hal Steinbrenner have stressed he has to show he’s not only sorry, but has also turned his life around for the better.

The free-agent market doesn’t offer many options either. Trevor Bauer could be available, but Bob Nightengale of USA Today reported two years ago that Bauer and Cole don’t quite get along.

Oh, and did I mention Luis Severino will be back from Tommy John surgery?

One way or another, the New York Yankees have pitching decisions to make, and none of them easy.

Readjust at the plate

This will not be a series of paragraphs saying how the Yankees must must MUST do something to fix the lineup that disappeared so often in both the regular season and playoffs. I made this clear at the start of the piece. The New York Yankees have a strong core and don’t need to overhaul the roster ahead of 2021.

More importantly, I said this last week: the Yankees’ lineup was actually decent despite Aaron Judge and Giancarlo Stanton missing time with injuries again. The Bronx Bombers were a top-five team in most offensive categories like OPS, home runs, wOBA, and WRC+. New York also led the AL in runs scored.

The problem was in deeper offensive stats, the Yankees were either in the middle of the pack or below. They ranked 14th in line-drive rate (LD%), 21st in fly ball rate (FB%), and 10th in groundball rate (GB%). Those aren’t ideal numbers for a team defined by home run power.

Thankfully, New York underachieving on offense in 2020 isn’t a referendum on the team’s talent. On top of an injury-ravaged lineup, all that can really be blamed for the team’s poor stretches at times is bad luck. The only way to really fix that is to go back and watch game film and have everyone adjust their approach accordingly. Hitting coach Marcus Thames is a conscientious guy, and he will absolutely make sure the proper adjustments are made.

This New York Yankees squad can absolutely win a World Series. If the front office stays the course and addresses these areas as needed, the team will win one.

Josh Benjamin has been a staff writer at ESNY since 2018. He has had opinions about everything, especially the Yankees and Knicks. He co-hosts the “Bleacher Creatures” podcast and is always looking for new pieces of sports history to uncover, usually with a Yankee Tavern chicken parm sub in hand.