The Phillies are playing a dangerous, probably smart game with Manny Machado

There are times in life where it makes sense to take calculated risks. Simply because it makes sense doesn’t mean that the risk is altogether eliminated, however.

Philadelphia Phillies general manager Matt Klentak is currently facing that dilemma in the team’s pursuit of Manny Machado. MLB.com’s Mark Feinsand reported last Friday that the Phillies were ‘moving on’ from Machado for the time being because the Orioles asking-price was too high. Jon Heyman of Fancred Sports tweeted Tuesday that while the Phillies are scouting backup options, Machado remains their No. 1 target. Of course he does. Machado’s been their No. 1 target for years. When managing partner John Middleton said during Spring Training that he’s “had names circled” for the 2018-19 offseason, it’s fair to assume that Machado was at the front of his mind.

At the same time, it’s reasonable for the Phillies to be hesitant to trade substantive young players – whether they are at the major league level or prospects – for Machado when he’s just months away from free-agency, and seemingly intent on testing the market. While there is a chance he enjoys Philadelphia so much that it gives the Phillies an overwhelming advantage in free-agency – while helping them reach the postseason in the interim – that’s certainly not a guarantee. The Los Angeles Angels, one of the league’s richer teams, traded for Mark Teixeira as a rental in 2008 and Zack Greinke as a rental in 2012. Both left in free-agency the following offseason. And that was back when you still got a compensatory pick when your rentals left in free-agency.

But again, there’s risk in not trading for Machado now.

In a perfect world, the Orioles will lower their asking-price for Machado, he’ll be dealt to Philadelphia and re-sign in the offseason. Heck, in a perfect world he would re-sign upon completion of a trade to Philadelphia. In a realistic world – one that’s not perfect, but not the worst-case scenario either – any of the Arizona Diamondbacks, Milwaukee Brewers, Cleveland Indians or even the Atlanta Braves would acquire Machado. While three of those four teams could prevent the Phillies from making the playoffs, none of them possess the financial wherewithal to retain Machado past 2018.

Popular: Curtis Granderson Could Make Sense As A Trade Target For The Phillies

Things get a little more dangerous when you talk about the Los Angeles Dodgers. While the Dodgers have Justin Turner entrenched at third base and shortstop Corey Seager set to return next season after having Tommy John surgery in late April, they have enough financial might to compete for Machado, who Bob Nightengale of USA Today said in Spring Training “would like to be on center stage in a big market.”

Retaining Machado past 2018 would require the Dodgers clearing quite a few hurdles. Second base has long been a hole for the Dodgers, but it won’t be filled by Machado. Despite winning two Gold Gloves at third base, Machado made clear to the collective media, including Jim Salisbury of NBC Sports Philadelphia, that he doesn’t intend to play anywhere but shortstop in the future. He’s certainly not moving to second base. One scenario could be that the Dodgers re-sign Machado, trade Turner and shift Seager to third base. Turner is one of the most popular Dodgers in recent memory, but at 33 (34 in November) would club president Andrew Friedman and general manager Farhan Zaidi let him stand in the way of them re-signing Machado? Most wouldn’t.

Moving Turner would also clear $19 million off of the $131 million in commitments that the Dodgers have for 2019

. Clayton Kershaw can – although he probably won’t – opt out of the remaining two-years and $65 million left on his contract at the conclusion of the 2018 season. Even if he doesn’t opt-out, there’s been speculation that the Dodgers could restructure his deal at the end of this season, by adding another opt-out and/or an extra year or two at the end. That will require quite a bit of their attention. Retaining Machado past 2018 would require appeasing a lot of moving parts, but is there a path to the Dodgers re-signing Machado, taking care of Kershaw and remaining competitive while staying below the luxury tax threshold (which is $197 million in 2018)? Yes.

And then there’s the New York Yankees.

In early February, Heyman, writing for FanRag Sports, wrote that the Yankese were viewed as “practically a slam dunk in some quarters” to land Machado’s  services. Then Didi Gregorius got off to a scorching-hot start to the 2018 season and both Gleyber Torres and Miguel Andujar shined as rookies. But if you thought the Yankees weren’t going to play a role in the Machado sweepstakes this summer (and probably in his free-agency this offseason), you were kidding yourself.

Ken Rosenthal of The Athletic reported Monday that the Yankees are “showing increased interest” in Machado, who turned 26 last Friday. Heyman added that general manager Brian Cashman has some interest in a deal that would net the Yankees both Machado and two-time All-Star closer Zach Britton. MLB.com’s Jon Morosi says the Yankees appear unlikely to part with pitching prospect Justus Sheffield for only a few guaranteed months of Machado. In all likelihood, Machado would have to shift back to third base for the rest of this season, something he’s made clear that he’s not interested in doing.

All that said, Machado doesn’t have a no-trade clause, so he couldn’t block any trade. He may not be in love with the idea of not playing shortstop, but it’s hard to imagine he wouldn’t prefer to play third for the 59-31 Yankees over playing shortstop for the 26-66 Orioles. The Yankees cross the box of allowing Machado to play in a major market. They are already among the World Series favorites for 2018, but would become the prohibited World Series favorite if they acquired the four-time All-Star.

If Machado won (or even competed) for a World Series with the Yankees, it’s difficult to imagine him leaving there this offseason. Perhaps the Yankees could talk him into playing third. Or they could re-sign him to play shortstop and trade Gregorius. Some would suggest that the Yankees would be better served spending money on their rotation than upgrading an already strong infield, but signing Machado would free-up any of the aforementioned three Yankees infielders to be moved in a package for a starting pitcher. Gregorious is 28 and under team control for 2019, there would be a market for him. And imagine the controllable starting pitcher the Yankees could acquire if they were willing to move either Torres or Andujar.

Phillies Nuggets: Did Odubel Herrera Get Snubbed For The All-Star Game?

Perhaps the scariest part about the Yankees potentially putting on a full-court press for Machado is they possess enough financial flexibility to compete with the Phillies in free-agency. The Phillies saving grace has always been the expectation that Middleton is going to offer Machado more money than any other suitor. But while some of the Yankees young talents figure to get expensive rather quickly in the next few years, they only have $86 million in financial commitments for 2019. If Machado spent a few months in blue pinstripes, the Yankees might just have to be competitive with the Phillies in free-agency to convince Machado to stay.

Does any of this mean that the Phillies should part with Zach Eflin or Adonis Medina for Machado, without a guarantee that he’ll stay in Philadelphia beyond the conclusion of the 2018 season? No, the logic of the Phillies drawing a line in the sand in trade talks with the Orioles makes sense. Beyond a lack of a guarantee that Machado will re-sign, you would rather keep your top young talents to build around him for the future if you can.

The Phillies still present an pretty attractive landing spot for Machado in free-agency. The Phillies are reportedly willing to accommodate Machado’s desire to play shortstop. Philadelphia isn’t New York or Los Angeles (ask LeBron James), but it’s still a top-five media market in the United States. And ask Cliff Lee what it’s like to play in Philadelphia when the Phillies are competing for World Series titles.

When Klentak and the Phillies brass drew a line in the sand with free-agent Jake Arrieta this past offseason, they ultimately got him on their terms – a ton of money annually, but only for three seasons. It’s smart to hold your own in any negotiations. But unlike Arrieta’s free-agency, the Dodgers and Yankees appear to be legitimately interested in Machado. And a few months in either market could be damaging to the Phillies chances of luring Machado in free-agency this offseason.