Yankees: 3 trades with Cubs that would be perfect if Chicago sells

PITTSBURGH, PA - SEPTEMBER 02: Kyle Hendricks #28 of the Chicago Cubs in action during the game against the Pittsburgh Pirates at PNC Park on September 2, 2020 in Pittsburgh, Pennsylvania. (Photo by Joe Sargent/Getty Images)
PITTSBURGH, PA - SEPTEMBER 02: Kyle Hendricks #28 of the Chicago Cubs in action during the game against the Pittsburgh Pirates at PNC Park on September 2, 2020 in Pittsburgh, Pennsylvania. (Photo by Joe Sargent/Getty Images)
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Kris Bryant #17 of the Chicago Cubs (Photo by Jamie Sabau/Getty Images)
Kris Bryant #17 of the Chicago Cubs (Photo by Jamie Sabau/Getty Images) /

Who are the New York Yankees? We’re about to find out over the next three weeks when the players on the field either convince the front office to buy or force them to sell at the trade deadline.

You know who else is in a similar predicament? The Chicago Cubs.

Once believed to be a legitimate dark horse contender to win the NL Central after an offseason that featured some wild trade rumors after they shipped Yu Darvish to San Diego, the Cubbies have come crashing back down to earth. This team was 38-27 on June 13. They’re now 42-44 (insert new record on Saturday).

The Brewers are among the best teams in MLB, the Cardinals are more built to buy than to sell regardless of how they’re playing, and the Reds are a pleasant surprise that could very well sneak in as a wild card if their offensive barrage continues.

Like the Yankees, the Cubs have three weeks to pick it up, but if we’re being honest with ourselves, it was always a long shot for them to be buyers at the trade deadline. They didn’t work to actively get better this past offseason and it’s a foregone conclusion they’re losing Kris Bryant this offseason.

So if Chicago decides to sell even more assets, how do they match up with the Yankees if general manager Brian Cashman decides to buy and Hal Steinbrenner opts to blow past the luxury tax threshold?

These three Yankees-Cubs trade would be perfect if Chicago decides to sell.

3. Kris Bryant to Yankees for Clint Frazier, Luis Gil and Anthony Volpe

Kris Bryant wouldn’t check all the boxes for the Yankees, but he gives them a much more potent back and viable defensive option in left field. If need be, he can play third base, too, which would help manager Aaron Boone with flexibility and giving guys rest.

Sorry Cubs fans, but this is Bryant’s last year in Chicago. You got your moment, though — the 2016 World Series was epic. Time to part with an asset before losing him for nothing!

This is the most unlikely of all the proposed trades, but it’s not out of the question. Bryant’s a rental and the Yankees have plenty to give. If he can reopen the team’s World Series window in 2021, that’ll change everything and revitalize the city. It’s not out of the question, either.

Why wouldn’t a package of Clint Frazier, No. 5 prospect Luis Gil and No. 11 prospect Anthony Volpe entice Jed Hoyer? Frazier, though downright bad in 2021, could benefit from a change of scenery. Beyond his vertigo diagnosis, he has no place on this Yankees team, especially if he continues to struggle on the big stage. That’s a controllable outfielder for the Cubs to work with for a few years.

Additionally, the Cubs always need pitching. Gil just hit Triple-A this year and rose fast after dominating at Double-A. He could hit the majors next year. His fastball sits in the high-90s, which is paired with a “power” breaking ball that is described as a slurve. His changeup continues to improve as well. He’s a starter right now, and has been good in that role, but some scouts see him as a high-leverage reliever.  Win-win, no?

As for Volpe, he could help the Cubs in the event there’s an issue keeping Javy Baez in Chicago for the long haul. There’s nobody in the Cubs’ system ready within the next couple of years to make the jump to MLB, and while Volpe’s timeline isn’t the most favorable, he’s tearing the cover off the ball at Single-A and should get the bump to Double-A for the second half. Assuming all goes well there, you’re looking at Triple-A in 2022 at some point. He’s a fast-rising prospect the Yankees simply may not have room for.

Better to get three players for Bryant than a lousy draft pick, right?

Ian Happ #8 of the Chicago Cubs (Photo by Dylan Buell/Getty Images)
Ian Happ #8 of the Chicago Cubs (Photo by Dylan Buell/Getty Images) /

2. Ian Happ to Yankees for Deivi Garcia and Estevan Florial

We’re not sure what’s happened to Ian Happ, but perhaps a change of scenery can do him good. The Yankees need a lefty-hitting center fielder, so come on down! We’ll take almost anyone at this point.

Sure, the Cubs might be hesitant to trade the slugger at his lowest possible value (he’s batting .184 with a .631 OPS), but how much longer do they keep trying with him? His rookie campaign in 2017 was a hit, but since then he’s either struggled or only contributed meaningfully in short spurts. Perhaps it’s time to move on.

Why not talk to the Yankees about one of their broken spare parts? Deivi Garcia, who was once believed to be a mid-rotation MLB starter, has fallen off a cliff at Triple-A after impressing at the major league level in 2020. We’ve seen what he’s capable of. Maybe he’s fallen flat in the minors because of his expedited move to the big league roster last year. He could help the Cubs rotation right now and for the next five years.

Florial is also almost MLB-ready. He got the bump to Triple-A after slugging the lights out at Double-A. He’ll probably need the rest of the year at Triple-A to find himself, but he’s a lefty slugger who can play all three outfield spots and has primarily held down center field the last couple of years.

This isn’t exactly a sexy trade for either side, but it helps with each team’s need and could provide a narrative change for these players. Perhaps the Cubs throw in a top-15 prospect (OF Cole Roederer), too, and call it a day?

Kyle Hendricks #28 of the Chicago Cubs (Photo by Justin Berl/Getty Images)
Kyle Hendricks #28 of the Chicago Cubs (Photo by Justin Berl/Getty Images) /

1. Kyle Hendricks to the Yankees for Oswald Peraza, Glenn Otto and Miguel Andújar

This is the big one. Even if the Cubs were selling, it’s unclear if Kyle Hendricks would be on the move, but that’s the player the Yankees probably need the most. They need someone behind Gerrit Cole consistently twirling quality outings.

Hendricks started the year off poorly and leads the NL in home runs allowed (20), but he also leads the NL with 10 wins and has lowered his ERA to 3.83 after it was … 6.23 two months ago! It’s been an epic rebound and he’s pitching like the bonafide No. 2 that he is. Nine of his last 10 outings have been quality starts. Keep it comin’!

The fact of the matter is that if the Cubs are going to orchestrate a rebuild, there’s no overarching need for Hendricks, who’s signed through 2023 at $14 million per year. The best use of his services would be to positively influence the next crop of young starters, which the Cubs can find elsewhere for cheaper.

And right now he can net them considerable assets amid his pre-deadline rebound. The Yankees would pay up, too, knowing Hendricks would help reopen their window over the next couple years and allow them to bump Domingo German from the rotation. Michael King is already out, and German can be discarded if the Yankees bring in Hendricks and get Luis Severino back. Then you’re looking at a Cole, Hendricks, Kluber, Severino, Montgomery rotation come late August. That’s … pretty damn good?

It won’t be cheap, though. For starters, ship over an MLB talent who can hit the ball but can’t really find a home defensively in Miguel Andújar. Call it a cost-effective lottery ticket. Why not? If his bat can be unlocked, then that alone is worth it.

Now let’s talk prospects. No. 4 Oswald Peraza is likely a must here. The shortstop is currently at Double-A after ripping through High-A. He still needs to progress through the minors, but the early returns are promising. Scouts have labeled him a plus player in terms of hitting, defense, speed and throwing. He’s been talked about as Gleyber Torres’ potential successor if Torres doesn’t work out. All good signs.

Now, forget about the rankings here for a second, Cubs fans. Glenn Otto might be the Yankees’ No. 28-ranked prospect on MLB.com, but he’s ripping through the ranks on Baseball America. The hard-throwing right-hander has been at Double-A since the beginning of the season and owns a 3.49 ERA and 0.94 WHIP (!) with an insane 95 strikeouts across 59.1 innings (10 games). He also dominated the Arizona Fall League in his last bit of minor-league action back in 2019. The dude is the real deal and could be in the majors by next season.

He’s come a long way with his command and throws a fastball, curveball, slider and changeup. If he continues to develop, we’re talking about a frontline rotation arm here. That should be enough to convince the Cubs, no?

The Yankees are going to have to give to get at this year’s deadline, so a trade will be painful (at least if you’re a prospect hugger). The time is now for the Bombers to rewrite their 2021 season. It should happen at (almost) any cost.

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