New York Yankees Manny Machado
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The New York Yankees are meeting with Manny Machado on Wednesday, but what is their real endgame with him?

Let the speculation, excitement, and anxiety begin, folks. As was reported earlier by George A. King III of The New York Post, Manny Machado and the New York Yankees will meet in person on Wednesday.

The hottest name on the free agent market not named Bryce Harper, Machado is expected to be paid well. Which team meets his contract demands, however, remains to be seen. Jon Heyman of Fancred reported the star infielder as already meeting with the Chicago White Sox.

ESPN’s Buster Olney added earlier this week Machado had meetings lined up with four teams.

And as MLB turns into the latest season of The Bachelor, the question asks itself.

What is the New York Yankees’ endgame with Manny Machado? Well, based on past history, your favorite Yankees columnist thinks he has the answer.

Where things currently stand

The biggest question regarding Manny Machado and the Yankees is simple: where would he play? The infield has a hole at shortstop, sure, but New York already has options. Gleyber Torres can just slide over from second base until Didi Gregorius is back from Tommy John surgery in the summer. This makes sense given Machado’s -6.1 career UZR at short, compared to his mark of 50.6 at third base.

Speaking of third base, the Yankees have that covered too. Well, at least for now. Miguel Andujar graded out as the worst defensive third baseman in baseball but also hit .297 with 27 home runs and 83 RBI. If the Yankees were to land Machado, that would make the infield very crowded, and present a dilemma once Gregorius came back.

Now that the stage has been set, this is probably what will happen between the Yankees and Machado. GM Brian Cashman will meet with the four-time All-Star, but not with the intention of signing him. Rather, the meeting will take place for another reason.

That reason is simple: drive up Machado’s price tag.

Cashman's strategy

Now, before we dive into how the Yankees will drive up Manny Machado’s price, consider the following. Last week, Heyman reported the Yankees were interested in Machado, but not enough to give him a $300 million contract.

Not only that but if the Yankees really were zeroing in on Machado, why are Andujar and Gregorius still on the team? If Cashman wanted to move Andujar with the intention of placing Machado at the hot corner, a deal could have been made at the Winter Meetings despite Andujar’s known defensive issues. His bat is strong enough suitors would have been lining up were he readily available.

Machado also said at the start of last season he wanted to stay at shortstop long-term, so why wasn’t Gregorius non-tendered? Cashman has already said he is interested in discussing a long-term extension with the fan favorite, so Machado doesn’t really have a concrete spot in New York.

It may not seem totally clear, but this is why the Yankees meeting with Machado makes perfect sense.

Past precedent

Alright, fans. Time to take a break from Manny Machado and go back in time to the 2014 offseason. This is when former fan favorite Robinson Cano hit the open market.

We all know how this story goes. Cano wanted a ten-year deal, the Yankees weren’t willing to offer that. Cano then inked a 10-year, $240 million deal with the Seattle Mariners. Naturally, fans weren’t happy and some even burned their Cano gear. I myself may or may not have wished serious ill will on him. Cano was a five-time All-Star who could hit for average and power, so why wouldn’t the Yankees make a bigger push to keep him?

Well, now that I’m a bit older and wiser, it’s easy to see why the Yankees didn’t give in to Cano’s demands. Cashman never wanted to re-sign him. This was confirmed in a story by Tyler Kepner of The New York Times, in which it was revealed Cashman actually wanted to trade Cano in summer 2013. His reason? He knew his second baseman wanted a 10-year deal and the Yankees wouldn’t be able to give him one. Sadly, owner Hal Steinbrenner didn’t allow a trade.

Granted, the Yankees did negotiate with Cano, but the Mariners ultimately outbid them. Fast forward to today, and Seattle just traded Cano to the New York Mets to unload his contract.

Why this makes sense

Now, let’s get back to Manny Machado. He’s one of the best hitters in the game, hit .297 with 37 homers and 107 RBI last season, and is still just 26 years old. The prime of his career has just begun, so he can easily demand a contract that pays him north of $300 million over several years.

Except, the Yankees are smarter than that. They probably see future free agencies with the likes of Chris Sale, Rick Porcello, and Mike Trout hitting the open market. Why spend $300 million and lose a draft pick on one player with questionable hustle when that cash can be saved for one or more of those three later on?

Now consider how polarizing the Yankees are as a team. They’re the Evil Empire. Adding Machado would further cement that reputation. Thus, by taking a meeting with Machado and publicly confirm “interest” in him, it sets up someone like the Philadelphia Phillies or another team entirely to get jealous and shell out even more money for Machado’s services.

It’s truly a game worthy of Jigsaw himself. Cashman knows he has a special roster already. Don’t forget, the Yankees won 100 games and were without Aaron Judge and Gary Sanchez for two months each. The AL East could be New York’s to lose if both stay healthy next year.

That said, better to let one team overpay Manny Machado and regret it later than be stuck holding the bag and be in another Alex Rodriguez situation.

It really is the perfect endgame, and watching to see how the Yankees come out of it is going to be exciting.

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.