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  • Manny Machado is almost certain to sign an industry-shaking contract with his next team. This is how we envision his free agency playing out this winter.
By SI.com Staff
November 27, 2018

Manny Machado is about to make a lot of money. Perhaps a record-setting amount, whether it be in the total value of his contract, the average annual value of it, or both. Sure, there are likely suitors that have been heavily speculated (see: Phillies). But past megadeals (Albert Pujols and Robinson Cano, namely) illustrate that teams can come out of nowhere when they believe a generational talent is within reach.

With that being said, this is where we envision Machado signing this winter.

Tom Verducci 

Phillies | 10 years, $330 Million (AAV: $33 million)

The money and need all match up between the Phillies and Machado. Yes, as we saw last month (and other times previously) Machado sometimes acts out foolishly and even recklessly on the field out of frustration. Yes, that will create some issues at times in Philadelphia. But he's too rare of a talent to pass up, especially since the Phillies' brass knows him from his early days with the Orioles. I've heard too many times how a postseason will diminish a player's value, only to see such players cash in (Yu Darvish, C.J. Wilson, David Price, et al). GMs look at value over years, not one postseason. Machado surpasses Giancarlo Stanton for the biggest contract guarantee, only to be leapfrogged by Bryce Harper.

Emma Baccellieri

Yankees | 10 years, $310 million (AAV: $31 million)

The Yankees have the resources to spend big in an open window of contention. (Then again, when do they not?) With plenty of young talent, New York's looking to compete both now and later, and that jives perfectly with a long-term deal for Machado. There's not any major infield reconfiguration needed to accommodate him, given that the team's reigning shortstop, Didi Gregorius, will miss the first half of the season while recovering from Tommy John and will be a free agent himself after 2019. Yes, Hal Steinbrenner did say that Machado's "Johnny Hustle" comments were troubling—but he later walked that back a bit, and anyway, Machado's makeup is one small part of a larger conversation about his talent and value.

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Stephanie Apstein

Phillies | 6 years, $250 million (AAV: $41.6 million)

Owner John Middleton vowed that the Phillies will spend money this year and “maybe even be a little bit stupid about” it. Maybe they will be creative instead: Machado probably didn’t cost himself dollars with his antics this postseason, but he may have cost himself years. If Philadelphia decides it needs to have him but doesn’t want to commit to building the franchise around him, a high-AAV offer might get his attention.

Connor Grossman

Yankees | 7 years, $285 million (AAV: $40.7 million)

When the Yankees want a star, they typically land a star. They don’t need Manny Machado, but there are short- and long-term reasons to think he’s a fit. Machado provides immediate relief at shortstop while Didi Gregorius recovers from Tommy John surgery. He bolsters an infield already rich in young talent with Miguel Andujar and Gleyber Torres. Might the Yankees eventually dangle one of those two as trade bait with Machado in the picture? Why not? I have doubts that Machado and fellow 26-year-old Bryce Harper will find the combination of contract length and value they’re looking for. A 10-year, $400 million deal isn’t likely to drop in his lap. But setting a new average annual value record seems inevitable for both young stars.

Gabriel Baumgaertner

Prediction: Yankees | 8 years, $300 million (AAV: $37.5 million)

Proposal: Dodgers | 6 years, $260 million (AAV: $43.3 million with opt-out after Year 3)

If you want to read about why the Yankees are the favorites to sign Machado, I encourage you to read two of my esteemed colleagues above. The calculus is pretty simple: the Yankees are in prime position to float third baseman Miguel Andujar to a team like the Giants in return for Madison Bumgarner and sign Machado. He's the perfect player for the Yankees to overwhelm their competitors in order to sign. While the prospect of Bryce Harper popping homers over the rightfield short porch is tantalizing, Machado is a better long-term option because of his defensive abilities.

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I'm going to make the case that the Dodgers should re-sign Machado by offering him fewer years and enormous average annual value and multiple opt-outs, even if the likelihood of them doing so is roughly zero. Machado didn't endear himself to the Los Angeles in his half-season in blue: he didn't hustle when he should have on multiple occasions, his on-field demeanor worsened when his struggles persisted, and he was never the terrifying plate presence in Los Angeles that he seemed to be in Baltimore. Since the Dodgers have Corey Seager returning to shortstop and Justin Turner manning third base, it seems foolish to even consider spending close to $300 million on a player whose atittude concerns are known to all. But Seager has battled back and elbow injuries over the last two seasons, worsened by the physical demands of shortstop. While the 24-year-old natural is an excellent defender, he's an unnatural build for the position at a sturdy, upright 6' 4".

Thus, the Los Angeles front office should move Seager to second base and fashion him after free agent D.J. LeMahieu, who also stands 6' 4". Seager won't reach free agency until 2022, so if the Dodgers sign Machado to, say, a front-loaded six-year, $260 million deal ($43.3 AAV) with an opt-out after the third year, Machado can reach free agency in the middle of his prime (age 29), after already banking some $120 million.

It's the best move for the Dodgers, whose championship window is still open, and for Machado, who can assuage concerns about his attitude while having two opportunities to become one of the game's richest players.

Jon Tayler

Yankees | 10 years, $335 million (AAV: $33.5) 

It’s not an offseason if the Yankees don’t do something big. All the angst over Machado’s much-derided “Johnny Hustle” comments doesn’t feel like anything more than a team’s forward-facing due diligence—ironically, the Yankees have to care about this in the same way Machado has to care about running out groundballs, as a matter of image. But in the end, Machado fits New York. He fills the hole at shortstop created by Didi Gregorius’ injury and turns the lineup into no-doubt the best in baseball. You can’t ask for much more than that.

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