Could the Phillies acquire Manny Machado and Zach Britton in the same deal?

For years, the Philadelphia Phillies have been speculatively connected to Baltimore Orioles shortstop Manny Machado and closer Zach Britton, both of whom can become free-agents at the conclusion of the 2018 season. This summer, the Phillies have substantively been connected to both stars. Could general manager Matt Klentak swoop in and acquire both in one deal before the July 31 non-waiver trade deadline?

Jim Salisbury of NBC Sports Philadelphia tweeted Friday evening that he’s “getting the vibe” that the Phillies may be “angling” to complete a mega-trade that nets them both Machado and Britton.

In a full story, Salisbury says that the Phillies have been “aggressive” in their pursuit of Machado in the past few days. He reported earlier this week that the Phillies had discussed Britton with the Orioles, who they defeated in a makeup game Thursday night.

Salisbury is among a slew of reporters to suggest that the Phillies appear to be making a serious push for Machado. Ken Rosenthal of The Athletic said Thursday that the Phillies had “increased their offer” for the four-time All-Star. He later added that the Orioles have been doing their homework on the Phillies farm system, something Salisbury echoed in his story. Jon Heyman of Fancred Sports says that the Phillies have made “progress” in their pursuit of the 26-year-old superstar.

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The Phillies entered Friday evening in first place in the National League East. Adding both Machado and Britton would seemingly cement their chances to return to the postseason for the first time since 2011. It may even make them the favorites to win the National League. But make no mistake, 2018 is the first year of the Phillies window of contention. They would be acquiring Machado and Britton with the understanding that it makes them a better team in 2018, but the realization that for what it would take to acquire the two, they would need to retain them past 2018 to win the trade.

Given the Phillies financial flexibility, it stands to reason that if they decided to retain Britton after the season, they would have a very good chance. Machado, regardless of where he finishes the season, is expected to test free-agency this offseason. But perhaps increasing interest from the New York Yankees, who seemingly would have a superteam if they landed Machado, has forced the Phillies hand.

If Machado was traded to the Brewers, Arizona Diamondbacks or Cleveland Indians, he would be a near lock to go elsewhere in free-agency. Even the Los Angeles Dodgers, with Justin Turner at third base and Corey Seager set to return to shortstop in 2018, might not be willing to outbid a team like the Phillies for Machado’s services this offseason. But the Yankees, that might be too much to overcome, especially if Machado got to experience wearing pinstripes for a few months.

Make no mistake, if the Yankees decide to seriously pursue Machado this offseason, they would present a potential roadblock to the Phillies. Although with Didi Gregorius under contract for 2019, Brian Cashman may try to sell Machado on returning to third base, the position that he won two Gold Glove Awards at. While in Philadelphia earlier this month, Machado made clear that he wants to remain at his natural position of shortstop, a position he returned to in 2018. It’s possible the Yankees could change Machado’s mind in free-agency. 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. So they could compete financially with anyone, all while offering him a chance to play with Aaron Judge, Gary Sanchez and Gleyber Torres for the most historically dominant team in the history of organized sports.

That pitch, in itself, could be very damaging to the Phillies chances of landing (or retaining) Machado in free-agency. But if he spends the rest of the 2018 season in New York and gets the feel of winning a World Series in New York, it’s almost unfathomable that he would leave New York. Even if the Yankees wanted him to stay at third. Even if the Phillies put a slightly higher offer on the table in free-agency.

However, Cliff Lee spent three months in Philadelphia in 2009, pitching the club to their second consecutive National League pennant. Even though he was traded that offseason, his brief stint in Philadelphia left so much of an impact on him that he returned to the Phillies in free-agency after the 2010 season, spurning the Yankees, and the Texas Rangers, who he had just pitched in the World Series with. The 2018 Phillies are not the 2009 Phillies. But is it possible that the Phillies feel that they would increase their chances to sign Machado this offseason if he A) spends a few months in a pennant race in Philadelphia and B) doesn’t spend a few months in a pennant race in New York? That checks out.

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However, as I wrote earlier this week, just because it makes sense to take a calculated risk doesn’t mean that the risk will pan out in your favor. The Phillies could trade for Machado and Britton (or just Machado), make the playoffs and still lose Machado in free-agency. Even if they were able to retain Britton, the trade would be a disaster if Machado left in free-agency.

Who would the Phillies have to surrender to land both Machado and Britton? Despite both being rentals, quite a bit, one would think. There are separate markets for both of the two, with six All-Star appearances between them. Britton is 30, but Machado is only 26.

Rosenthal noted that RHP Adonis Medina, the Phillies No. 2 overall prospect, is someone that the Orioles have interest in. He previously said the same about injured shortstop/third baseman J.P. Crawford. Salisbury added a few other names of interest to the Orioles; shortstop Arquemedes Gamboa, the No. 8 overall prospect in the Phillies system; RHP Franklyn Kilome, the No. 7 overall prospect in the Phillies system; LHP Ranger Suarez, the No. 9 overall prospect in the Phillies system and outfielder/first baseman Jhailyn Ortiz, the Phillies No. 5 overall prospect. He speculated that Enyel De Los Santos, Maikel Franco and Aaron Altherr also could be of interest. The Phillies obviously wouldn’t trade 10 pieces even in a trade of this magnitude, but these are some of the names that could be included if a trade like this came to fruition.

If the Phillies traded for Machado and Britton before the July 31 non-waiver trade deadline, the city would be ready to erect statues of Klentak, Andy MacPhail and John Middleton. However, if the Phillies traded a bounty to land Machado (with or without Britton) and he left in free-agency, it could turn out to be the defining move of Klentak’s tenure.