The most at risk in high-stakes Manny Machado sweepstakes
21st December 2018

Manny Machado — no matter where he lands — will soon receive a guaranteed contract worth hundreds of millions of dollars.

Whichever team secures Machado will import a great talent in his prime.

Sounds perfect, right?

Except this is high-stakes free agency: Machado encountering his one best shot to make this kind of score while teams decide their breaking point for a star.

So who has the most pressure on them?

1. Machado: This would be simple if the Yankees were operating in a way familiar to their past — overreacting and overpaying after a Red Sox title. Because all indications are the Yankees are Machado’s preference. So, if Brian Cashman came to their dinner meeting Wednesday night waving a blank check, this would be where easy meets peasy for Machado.

But the sense is the Yankees are a split camp in how much to offer Machado, and if they even should go down this path at all or save for when an area of greater need arises. The Phillies, for near certainty, and possibly even the White Sox are poised to outbid the Yanks.

There was a time when it was thought Machado would top the records for largest overall contract (Giancarlo Stanton, $325 million) and annual average value (Zack Greinke, $34.4 million). He still might. But the Yankees do not seem in that financial frame of mind.

So what happens if, for example, the Yankees bid seven or eight years at $30 million annually, and the Phillies show a willingness to exceed $300 million? The history is that players will follow the money over their hearts. Will Machado?

2. John Middleton: The Phillies have been cleaning up their payroll for years with an eye on the free-agent offseason of Machado and Bryce Harper. Then Middleton, their principal owner, declared they were ready to be “a little stupid” about spending.

Phillies officials have tried to lower the impact of that statement since, claiming ownership and baseball operations are simpatico and that all would be fine with upgrading the club and missing out on Machado and Harper. But the understood promise to the fan base has been Machado or Harper — maybe even both — and to walk away with neither would play as defeat. An offseason of Jean Segura, Andrew McCutchen and a couple of relievers is not going to work in a town that just had a Super Bowl champ and is seeing the 76ers’ Process mainly come to fruition.

The word at the winter meetings was the Phillies preferred Machado over Harper, so does this owner have to write a check that assures Philly gets its man?

3. Hal Steinbrenner: In the decade-plus running the Yankees, Hal Steinbrenner has defined himself apart from his father by being more patient and thoughtful in personnel moves. Machado would be more of a George move because there is not unanimity in the Yankees ranks that Machado is the right play.

Didi Gregorius should be back by midseason, Miguel Andujar may turn out to be an All-Star third baseman. The Yanks can short-term protect themselves in case either does not work out. Signing Machado pretty much means giving up on Gregorius long term or Andujar as a third baseman, plus tying up lots of future cash and maneuverability.

If the Yankees sign Machado, it would be because Hal dictated the decision. That would sate parts of his fan base screaming for him to do exactly this and act more like his dad to fulfill tacit promises to spend big in the year after sinking beneath the luxury-tax threshold.

My gut says that faced with a split camp, Hal might try a measured pursuit that would not set records and would keep Machado for almost all prime years — something like a seven-year, $210 million bid. That is the opposite of a Godfather proposal — an offer Machado could refuse. Especially if Middleton comes with a much larger check or the White Sox do the same or if Machado’s desire is to try to outdo Harper financially.

What will the teams and Machado do?

The pressure is on.

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