Yankees: 5 trade deadline targets for NYY as Aug. 31 rapidly approaches

The New York Yankees actually have to think about the trade deadline now. Weird.

As difficult as it’s been to adjust our vocabulary while facing a 60-game season amid a pandemic, the New York Yankees are contenders for the World Series, and the trade deadline presents an opportunity for them to improve their roster on Aug. 31.

Oh, yeah, only a few issues: Eight teams make the playoffs per league, essentially every team in baseball is still in the race, and there are significant moral implications of trading a player across the country while the very act of travel remains pretty unsafe. But other than that, we’re good to go!

In this hypothetical, we’ll have to pretend that the literal mechanics of trading are hunky-dory. As of this writing, we have zero idea how the league will treat this deadline, and whether there’ll sort of be an informal agreement that maybe we just don’t do trades this year.

For now, though, it’s fair to assume the have-nots who’ve already revealed themselves will be willing to deal, and contenders would prefer to plunder them.

These five targets could be good fits for the Yankees, with very limited options available.

5. Tony Watson

The Yankees would love to deploy Giants lefty Tony Watson.

The San Francisco Giants are the likeliest team in baseball to dip into their reserves this deadline.

After all, prior to the pandemic, they’d seemingly built a roster begging for one final tear-down. An offense without power or much promise, a pitching staff with a few high-priced veterans in their contract year (we’ll get to them), and a decent bullpen, led (in theory) by Tony Watson.

Though Trevor Gott has been getting most of the Giants’ high-leverage work this season (and will now be known for face-planting against the A’s after Gabe Kapler placed all his faith in him), the 35-year-old Watson remains a dominant lefty in the shadows, and would be perfect in New York.

Even if Tommy Kahnle were healthy, it would be nice to have a high-leverage lefty like Watson, less of a platoon arm than Luis Avilan in the three-batter minimum era, and the first left-handed relief ace the Yanks would’ve imported since Justin Wilson.

In 5.2 innings thus far in 2020, Watson has a 1.69 ERA, and could be of far greater use to a contending team than a franchise perpetually stuck in between. C’mon, Giants. It’s an even year. Help us make magic.

4. Greg Holland

Greg Holland might be the most effective reliever available to the Yankees.

Casual fans might not realize the number of ups and downs Greg Holland went through between dominating for the 2014 Royals and dominating for the 2020 Royals. If you’ve only watched him a few times, it would appear that nothing had changed, despite the extreme grind it took to get to this point.

The 34-year-old Holland was dominant in 2013 and ’14, losing a bit of his effectiveness as Wade Davis and Kelvin Herrera took the spotlight for the World Champions in 2015. Since then, he’s missed the 2016 season, gotten back to a baseline of dominance in posting an All-Star season for Colorado in 2017, and been a viable reliever, at the very least, with the Cardinals, Nationals and Diamondbacks since then.

Upon returning to KC in 2020, Holland’s once again showcased strong stuff and veteran guile for contenders who need it, posting a 2.61 ERA through his first 10 outings. The Royals are on the fringes of the Wild Card race (once again, 2020 is weird), but they have to be wise enough to realize that would be the case whether they had a veteran reliever like Holland or not.

Man-bunned Josh Staumont has emerged as their best relief option, and they’ll keep leaning on him. Holland is simply pitching well, biding his time for a more high-profile opportunity.

2. Martin Perez and … Other Red Sox Targets

We’re sorry, but we at least have to *talk* about the Yankees trading with the Red Sox.

So few teams are bad this year! So few! And one of them’s the Boston Red Sox. What can you do?!

Odds are, Chaim Bloom would love to trade with his chief rivals this year, considering most of the available Red Sox feel like ticking time bombs.

Martin Perez, on a one-year deal, is really the only arm who makes sense … for anyone, and he’s been a viable major-league starter this year, posting a 3.38 ERA and stymieing the Rays in Tampa. He’s certainly better than JA Happ — but, then again, so is Clarke Schmidt, and we’re still sitting here doing this dance. Perez’s handling of the Yankees this week could very well determine his standing with the organization.

But could this go deeper? The Red Sox made it clear this week that nobody is untouchable. They’re not trading Xander Bogaerts or Rafael Devers to the Yankees — is there anyone else they’d want? Nathan Eovaldi comes to mind, but odds are that’d be a classic Boston hoodwink, and he’ll revert right back to his Yankees form when he arrives, two more years of a massive contract (four years, $68 million) in tow. He’ll absolutely forget how to make his fastball move if he shows up on our doorstep. Bank that.

JD Martinez would be fun to steal, but we don’t need another DH who could opt out (and is struggling). Kevin Pillar would be fun outfield depth? Ditto Jose Peraza for second base, if DJ LeMahieu misses more time than expected. Let’s keep this stupid team on speed dial.

1. Johnny Cueto

Johnny Cueto is the best pitcher on the market, and the most joyous fit for the Yankees.

With James Paxton downgraded to “solid, but still searching” and JA Happ essentially unplayable, the Yankees could use one, perhaps two, rotation upgrades, depending on how much Pax you’re willing to tolerate.

Clarke Schmidt, hanging out at the Alternate Site, would be an incredibly easy maneuver. But, in terms of a veteran who’s about to hit free agency and will likely be at his lowest-ever cost, it’s hard to beat the injection of joy that Shimmying Johnny Cueto would give us. Also … you could use both Schmidt and Cueto in September! How ’bout that! What a country.

In five starts, the now-healthy Cueto has a 4.62 ERA, but he was betrayed by Hunter Pence’s defense midway through a no-hit bid against the Dodgers, leading to a downward spiral that’s marked up his numbers in a shortened campaign. Sandwiched around that start were five two-earned-run innings at Coors Field, and seven two-run innings against the streaking A’s. Cueto can still pitch and, let’s face it, even his losses are more fun than whatever Happ can deliver, with his wild array of windups and quirks.

Every Happ start is repetitive, flat torture. Every Cueto start is a new, weird odyssey. We’re all in on at least trying it.

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