In what has been a slow offseason around baseball, the New York Yankees remained busy Thursday afternoon. They reportedly agreed to a three-year contract with free agent right-hander Adam Ottavino. He joins Aroldis Chapman, Dellin Betances, Chad Green, and the recently re-signed Zach Britton to form a devastating bullpen corps.

The pending Ottavino signing -- the Yankees still have not announced the deal, though that'll happen soon enough -- is the fourth free agent signing the Yankees have made in the last four weeks and their sixth notable transaction this winter. Here's the list:

  • Nov. 19: Acquired James Paxton from the Mariners for three prospects.
  • Dec. 17: Re-signed J.A. Happ to a two-year, $34 million contract (with 2021 option).
  • Jan. 4: Signed Troy Tulowitzki to a one-year, league minimum contract.
  • Jan. 11: Re-signed Britton to a three-year, $39 million contract.
  • Jan. 14: Signed DJ LeMahieu to a two-year, $24 million contract.
  • Jan. 17: Signed Ottavino to a three-year, $27 million contract.

The Yankees also re-signed veteran stalwarts Brett Gardner and CC Sabathia to fill complementary roles. Paxton and a full season of Happ improve the rotation, Ottavino and a full season of Britton strengthen the bullpen, and Tulowitzki and LeMahieu provide infield depth as Didi Gregorius rehabs from Tommy John surgery.

As active as they've been, the Yankees have taken small nibbles (relatively speaking, of course) rather than one or two great big bites this offseason. Spreading the money around can work, absolutely. The 2013 Red Sox won the World Series that way. The Yankees have not yet made that huge splash despite being perfectly positioned to do so over the winter. Consider two things:

  1. The Yankees have developed a cheap homegrown core led by Aaron Judge, Luis Severino, Gleyber Torres, Miguel Andujar, and Gary Sanchez. That is the foundation of the team that won 100 games in 2018.
  2. The Yankees stayed under the $197 million luxury tax threshold in 2018. That reset their tax rate after years and years of being taxed at the maximum 50 percent for every dollar spent over the threshold.

The Yankees have a great (and cheap!) young core and they are better positioned financially with regards to the luxury tax than they have been at any point since the luxury tax came into existence in 2003. Add in getting thumped by their historic rival in the ALDS and it would seem the Yankees were all set to do some real damage this offseason.

Instead owner Hal Steinbrenner, general manager Brian Cashman, and everyone else in the team's brain trust have remained remarkably disciplined, opting to address as many roster needs with short-term contracts as possible. As a result, the Yankees are a much deeper team now than they were a year ago, and remember, they won 100 games last year.

That said, I can't shake the feeling the Yankees are missing out on giant opportunities this offseason. Giant opportunities named Manny Machado and Bryce Harper. The Yankees are a very good team, that was the case last season and it will be the case again this season. Adding Machado and Harper to the mix would cement them as a clear-cut favorite going forward.

Thus far the Yankees have resisted serious runs at Machado and Harper. They did wine and dine Machado at Yankee Stadium last month and are reportedly in the hunt, but only on the periphery. As for Harper, the Yankees have not been connected to him at all this winter. It's very odd. You'd think they'd be more involved simply out of due diligence. Not the case though.

As long as Machado and Harper remain unsigned -- their free agencies could drag on much longer considering spring training is still a month away -- I would not rule the Yankees out as a landing spot. Thus far though, they are either uninterested or playing it extremely cool. Here are four reasons why the Yankees should cap off their offseason with Machado or Harper.

Free agents like this don't come around often

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Machado or Harper? Harper or Machado? USATSI

It has been a very long time since we've seen a 26-year-old bona fide superstar reach free agency. You have to go back to Alex Rodriguez during the 2000-01 offseason. This offseason there are two such players in Machado and Harper. They are already All-Star caliber producers and they're about to enter what should be the best years of their careers.

Players like this rarely become available for nothing but cash (and a draft pick, in Harper's case) and, when you play in the game's biggest market and you have a great young core, you should jump at the chance to supplement that core with someone like Machado or Harper. Machado and Harper are younger than Aaron Judge, you know. Look it up.

Point is, players this good and this young are very hard to acquire. This would not be giving 32-year-old Albert Pujols a 10-year contract or giving the highly flawed Chris Davis a seven-year contract. Machado and Harper are on the Hall of Fame track and they are in their prime. Sign them while you can. The opportunity doesn't come along often.

They both want to be Yankees

Remember way back in the day when Harper was on the cover of Sports Illustrated as a 15-year-old? Here's what Harper told Tom Verducci for that article:

When asked about his goals as a ballplayer, Bryce replies with certainty.

"Be in the Hall of Fame, definitely. Play in the pinstripes. Be considered the greatest baseball player who ever lived. I can't wait."

Play in pinstripes, eh? Several big league teams have pinstriped uniforms but, when someone says "play in the pinstripes," you instantly know they're talking about the Yankees. Playing in New York is apparently something that has been on Harper's mind a very long time.

As for Machado, it has been an open secret that he would like to play for the Yankees for a while now. It has been reported for years. Here's what CBS Sports' Jim Bowden wrote for The Athletic last month:

Machado has told friends in Miami that his preference is the Yankees, and if the offers are close, he'll be headed to the Bronx. 

Machado and fellow Miami native Alex Rodriguez are close and Machado reportedly wants to follow in A-Rod's footsteps. Also, A-Rod is a special advisor with the Yankees now. I'm sure he's done some lobbying these last few weeks and months.

At the end of the day, I imagine Machado and Harper will base their free agent decisions on money. They might not end up with the $400 million they were seeking, but they're going to get paid handsomely. When superstar players want to wear pinstripes, the Yankees should take advantage. I wouldn't count on a discount, but you have to find out just how badly they want to play in the Bronx.

The Yankees have to money to sign everyone

Everyone. Machado, Harper, Dallas Keuchel, Craig Kimbrel, Mike Trout in two years, Judge to a big money extension. Everyone. In 2017, Forbes estimated the team's annual revenue at $619 million. That was before the Yankees received their cut (reportedly $50 million per team) of the league's BAMTech sale to Disney and their cut of the league's new gaming partnership with MGM, however much that is. The Yankees are swimming in money Scrooge McDuck-style.

Of course operating expenses and revenue sharing and ballpark construction costs must be subtracted from revenue. Making $619 million in revenue doesn't mean you can spend $619 million in players. It does mean you can spend a lot on players though, and the Yankees are, just not as much as they have in the not-too-distant past. Here are the club's end-of-season payroll numbers the last five years according to Cot's Baseball Contracts:

  • 2014: $218.46 million
  • 2015: $223.56 million
  • 2016: $243.79 million
  • 2017: $224.22 million
  • 2018: $192.98 million

The Yankees spent nearly $51 million -- $51 million! -- more on payroll in 2016 than they did in 2018. With revenues continuing to climb, of course the Yankees can support a higher payroll than the one they carried in 2018. They got under the luxury tax threshold and reset their tax rate. The penalties for exceeding the threshold will be much less severe going forward.

Once you add in Ottavino, Cot's gives the Yankees a projected $220.74 million payroll for luxury tax purposes this coming season. At some point the Yankees are going to trade Sonny Gray and his $7.5 million salary. It is inevitable and it could happen soon:

These days there are several luxury tax threshold tiers with increasingly harsh penalties the higher you go. The first tier is $206 million, the second is $226 million, and the third is $246 million. Go over the $246 million threshold and you get hit with a surtax and also have your first-round pick moved back 10 spots. That stings.

It's also a small price to pay when you're adding Machado or Harper to your roster. Trading Gray and his $7.5 million salary leaves the Yankees roughly $33 million short of the $246 million threshold. Can the Yankees swing it so that they trade Gray, add Machado or Harper, and stay under the $246 million threshold? Maybe. The larger point is the Yankees have the money. They ran a $243.79 million payroll three years ago. Sign Machado or Harper and they're at the same level now.

The Yankees can fit them into the lineup

I'd argue that, when you have a chance to acquire a player like Machado or Harper, you get him and figure out the roster later. Get the elite talent and make it work. In Machado's and Harper's case, the Yankees could make either work within their roster easily. Consider the two scenarios:

1. Sign Machado to play third. It could just be talk, but the Yankees seem very committed to Tulowitzki at shortstop while Gregorius is on the mend from elbow reconstruction. That's fine. The Yankees could still play Tulowitzki at short, Machado at third, and Andujar at first base with LeMahieu filling the super utility role the Yankees signed him to play. A possible lineup:

  1. CF Aaron Hicks
  2. RF Aaron Judge
  3. 3B Manny Machado
  4. DH Giancarlo Stanton
  5. 1B Miguel Andujar
  6. C Gary Sanchez
  7. 2B Gleyber Torres
  8. SS Troy Tulowitzki
  9. LF Brett Gardner

Should Tulowitzki get hurt or fail to produce, the Yankees could slide Machado over to shortstop until Gregorius returns, and roll with Andujar (or LeMahieu) at third base. Easy peasy.

2. Sign Harper to play left. Last year Harper split his time between center and right, and he's been a full-time right fielder for several years now. Harper did initially break into the big leagues as a left fielder in deference to Jayson Werth though. He didn't move to right for good until 2015. The Yankees could put Harper back in left field and move Gardner to the bench in a fourth outfielder's role. Far-fetched? Not really. Gardner went to the bench after the Yankees acquired Andrew McCutchen last year. 

There has been speculation about Harper possibly playing first base but, to me, that seems like a waste of his athleticism. The more likely scenario has Judge or Stanton moving to first base given their massive frames. How much longer can they run around the outfield at that size? Here's a possible lineup with Harper in left field:

  1. CF Aaron Hicks
  2. RF Aaron Judge
  3. LF Bryce Harper
  4. DH Giancarlo Stanton
  5. 3B Miguel Andujar
  6. C Gary Sanchez
  7. 2B Gleyber Torres
  8. 1B Luke Voit
  9. SS Troy Tulowitzki

It should be noted the Yankees will be extremely right-handed this coming season. Their only left-handed hitters are Gardner and Hicks, a switch-hitter, until Gregorius returns. Harper's lefty thump would balance the lineup nicely. That lineup there is thunderous and it leaves the Yankees with two quality reserves in LeMahieu and Gardner on the bench. A very deep offense, it would be. The Yankees can make Machado or Harper fit if they want.


As quiet as the Yankees have been in the Machado and especially the Harper bidding, I would never rule them out on a star free agent until I see that player wearing another team's uniform. To me, Harper is the better fit for the Yankees. I think he'll be a better player than Machado the next five years and it seems he fits the roster and lineup a little more neatly. A high on-base lefty bat is the one thing the Yankees are missing.

Financially, the Yankees can swing it. Every team can swing it financially, really, but we know for certain the Yankees can. We've seen them carry the sort of payroll required to land Machado or Harper just a few years ago. Machado and Harper want to be Yankees too, and it's not like 26-year-old mega-talents hit free agency every winter. The Yankees have done nice work spreading the money around and adding depth to their roster this winter. Signing Machado or Harper would be icing on the cake.