yankees vs phillies betting preview odds picks prediction
(Photo by Mike Stobe/Getty Images)

The New York Yankees have a lot to consider this offseason. Here are some predictions for what the Bronx Bombers’ winter could entail.

As the World Series plays on, the New York Yankees are in offseason mode.

The team has a lot to consider for 2021. The COVID-19 pandemic meant the Yankees (and all other teams) suffered major financial losses, losses owner Hal Steinbrenner called “more than any other team in baseball” in an interview with ESPN’s “The Michael Kay Show.”

Additionally, Bob Klapisch of NJ.com raised an interesting point. Despite those losses, the Yankees need to decide whether to cut payroll below the luxury tax threshold next season or stay the course. This decision is made more difficult by the Yankees’ several impending free agents, namely Masahiro Tanaka and DJ LeMahieu.

Who will sign? Who will leave? Which decisions will help or harm general manager Brian Cashman, not to mention his team which so desperately craves a championship?

Let’s look inside the crystal ball and see if we can guess what happens in the Yankees’ future.


Tanaka stays put

This should almost go without saying, but Masahiro Tanaka needs to be an offseason priority for the New York Yankees. The veteran righty had his ups and downs, but was largely reliable in his first seven years in pinstripes. In the playoffs alone, he owns a 3.33 ERA, and it’d be even lower had he not tipped his pitches this year.

And when push comes to shove, chances are the Yankees will re-sign Tanaka. Remember, he could have opted out after the 2017 season. Rather, he opted in for the final three years of his deal to try and win a World Series playing for manager Aaron Boone.

Moreover, Tanaka just has that career Yankee “it” factor. There’s just something about him that makes the idea of wearing other than pinstripes near-impossible to grasp. He made $22 million a year in his first contract and should expect to receive less as he turns 32 next month.

That said, assuming both sides want a reunion, I fully expect Masahiro Tanaka to take a hometown discount. It might just mean Cashman offering a six-year deal instead of five. Either way, Tanaka is worth it.

So does LeMahieu

DJ LeMahieu has done more in two years with the New York Yankees than anyone could have imagined. In 2019, he set career highs in home runs and RBI. In 2020, he hit .364 and became the first MLB player to win batting titles in both leagues. LeMahieu also led the AL in OBP, OPS, and OPS+ despite missing 10 games with a thumb injury.

Now, consider the role LeMahieu plays on the Yankees outside of the batter’s box. He’s a Gold Glove second baseman, but often plays third base and first base, particularly in the later innings. He truly is a two-way player in that his hitting and fielding are on equal levels.

Furthermore, LeMahieu is on record saying he’d love to stay. He won’t be cheap, but what other options do the Yankees have for their infield? Start Tyler Wade at second base and hope his bat finally wakes up? Teach Miguel Andujar to play the position when he’s already a shaky fielder? How about rolling the dice on the streaky Jurickson Profar in free agency in hopes he becomes Gio Urshela 2.0?

No, the Yankees won’t be so tight-fisted as to let someone as important as LeMahieu walk. He’ll want more than the $12 million a year he made on his first Yankee contract, but adding an extra year again could mean a hometown discount.

J.A. Happ signs with a division rival

Though J.A. Happ’s contract included a $17 million vesting option for next season, the New York Yankees worked to ensure he didn’t meet the thresholds. Sure enough, Happ and Cashman’s relationship has since soured. It doesn’t matter that Happ pitched to a much-improved 3.47 ERA and 1.05 WHIP. There is literally zero way the tall lefty stays in New York.

Consider where Happ is in his career. He just turned 38 and can’t have many years left in his arm. This means as he winds down his career, it’s time to chase rings. It just so happens the division rival Tampa Bay Rays are currently playing in the World Series.

Now, consider the fact that Happ owns a home in Clearwater, Florida, just a short drive away from Tropicana Field. The Rays don’t spend money often, but why wouldn’t they take a one-year flier on a veteran who could give them a further advantage over New York?

In professional wrestling, this is what fans call a heel turn. Happ signing with Tampa Bay wouldn’t be the same as, say, Stone Cold Steve Austin aligning with Vince McMahon to beat The Rock at Wrestlemania X-Seven, but not too far off. Happ could also explore a return to the Toronto Blue Jays, who traded him to New York in 2018.

One way or another, Happ isn’t coming back and will probably take some parting shots at the Yankees whenever he signs elsewhere.

James Paxton accepts the qualifying offer

James Paxton would rather forget 2020. Offseason back surgery plus the pandemic delaying the season meant his fastball velocity dipped. He adjusted, but still posted a horrific 6.64 ERA before injuring his elbow. To add insult to injury, this happened in his contract year.

Normally, I would say Cashman wouldn’t even extend Paxton the $18.9 million qualifying offer. However, look at the Yankees’ projected pitching rotation. Gerrit Cole and Jordan Montgomery are the only surefire locks. Deivi Garcia is talented and has a high ceiling, but is still largely untested as is prospect Clarke Schmidt.

And if Tanaka signs with a new team, the New York Yankees will desperately need arms. Thinking about it now, they don’t really have a choice but to offer Paxton the QO. Given his season, he would be smart to accept it as a sort of “prove it” deal. If he declines it, the Yankees get a draft pick from whichever team signs him.

One way or another, deciding on James Paxton isn’t as easy as it seems. In this case, his being offered and then accepting the QO seems all but inevitable.

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.