Grading the Yankees-White Sox trade

Rick Hahn, GM of the White Sox, went to sleep on Oct. 2, 2016, after the 162nd game of another disappointing season, presumably bleary eyed and with a whole a lot to think about. The White Sox had two of the best pitchers in the American League, and they still couldn’t win more games than they lost.

Hahn went to sleep on July 18, 2017 on a pile of prospects. If they complained about being uncomfortable, he told them he would get new prospects who didn’t complain. They stopped complaining.

Between those two dates, the White Sox had acquired the no. 1 prospects from the Red Sox, Nationals, and Cubs, all of whom had highly regarded systems. Of the top 10 White Sox prospects on MLB Pipeline’s, eight have them have joined the organization in the last nine months, seven of them by trade. Seven of them are in baseball’s top 70.

Brian Cashman, GM of the Yankees, went to sleep on Oct. 4, 1992, when he was the assistant GM, after the 162nd game of another disappointing season, presumably bleary eyed and with a whole a lot to think about. They haven’t finished a season under .500 since. They weren’t going to finish under .500 this season, and they’re a better team now. That’s so Yankees.

Both teams are looking bold and clever after the White Sox traded Todd Frazier, David Robertson, and Tommy Kahnle to the Yankees for four prospects, including their 2016 first-round pick, Blake Rutherford. The Yankees got relievers (more of them). The White Sox got prospects (more of them). Which means we’ll need to GRADE THE TRADE. So I’ve set a reminder for 2021 to come back and do just that. Check back then, and we’ll let you know how the Yankees did in the postseason, and how the prospects developed for the ...

[editor whispers in my ear]

Right now? But that’s absurd. You can’t ...

[editor talks a lot louder in my ear, and frankly gets quite rude]

Well, fine, whatever, let’s grade this trade

No idea. Check back in a few years.

Aaaaaand I’m hearing footsteps, so let me clarify that. Blake Rutherford doesn’t have the most impressive stats for a 20-year-old in Low-A, but he has the tools and the pedigree, and prospect mavens are smitten with him. Ian Clarkin hasn’t missed a lot of bats in his minor league career, and he doesn’t have an upper-90s fastball, but the former supplemental first-rounder has kept runs off the board. Tito Polo was one of the prospects the Yankees got from the Pirates in the Ivan Nova deal, and while he’s the least known player in the deal, he’s proven he isn’t a fish out of water in the minors.

All three could fail to make the majors. All three could dominate and turn this into a Grady Sizemore, Bartolo Colon, and Cliff Lee-type trade. But you know this, and it’s useless for you to read the evaluations of someone uncomfortable evaluating prospects. So I’d like to grade the timing of the White Sox.

The White Sox traded Chris Sale roughly at the peak of his value. That is, at the peak of his value once it was reasonable to trade him. Once it was clear that the team had no idea how to build a winner around him, and that they wouldn’t figure out how to do that until he was much closer to free agency, they traded him for a stellar package that included a radar-breaking flamethrower and one of the very best prospects in the game, if not the consensus best. They timed it perfectly.

They traded Adam Eaton roughly at the peak of his value. His low-cost contract, gaudy WAR, and the leverage held by the White Sox forced the Nationals to give up a couple of their best prospects. The White Sox timed it perfectly.

They traded Jose Quintana a few months after the peak of his value. But, somehow, emerging from the murky offseason waters made teams a little more desperate, a little more aware of their acute needs, and that made teams bid even harder? The White Sox timed it perfectly, even after it looked like they screwed up the timing.

They traded Todd Frazier long after the peak of his value, and I’m not sure how much value David Robertson really had with his big contract, but they turned a minor deal for Tommy Kahnle back in 2015 into another prospect windfall, escaping from some of Robertson’s contract and getting value for Frazier after all. They didn’t wait for Kahnle to remember that he wasn’t supposed to throw strikes, and they didn’t do the classic rebuilding mistake of holding on to their best relievers to protect leads they weren’t going to have. They timed it perfectly.

The White Sox might be years away from contending, but when I wrote about the Astros back in 2014, I looked at the struggling teams with top-five farm systems and how they fared in subsequent years.

We’re dealing with a small sample -- just 15 teams. But in the last decade, there have been 15 teams who placed in the top five of a Baseball America farm-system ranking, and only one of them didn’t make the playoffs within four seasons. The one that didn’t made it in the fifth season. Only three of the 15 weren’t over .500 four seasons later.

That isn’t to say that a prospect ranking is something that guarantees success. But it’s the sign of an organization that’s doing something right, and an organization that does something right is more likely to do several things right. The White Sox targeted the best prospects in baseball, and they nabbed them in an era when teams are extremely reticent to trade them. That’s evidence that the White Sox front office possess a level of craftiness and skullduggery that will serve them well.

Grade (for the whole thing, the timing of it all): A

I won’t even drop a “wait until they make the postseason” on you. Because you’ll really need to wait until the deadline to see if the can add another pitcher, or a first baseman who can push Chase Headley to the bench.

If they get a first baseman (or, I guess, another third baseman and move Frazier to first), they’ll have an even more absurd lineup. If they get another starter to replace Michael Pineda, they’ll have the support they were counting on in the first place. And if they have some or all of that, they’ll be in solid position to make the postseason.

And if they make the postseason, oh, buddy. This is the template. This is the dream. The Indians made it to Game 7 of the World Series with one ace and a bullpen of doom. The Royals won two pennants and a World Series with a bullpen of doom. While Aroldis Chapman is a lot dodgier than he should be, here’s what the Yankees are hoping for:

Fourth inning: Aaron Judge swats a dinger to give the Yankees a 4-3 lead
Fourth inning: CC Sabathia gets out of trouble, is exhausted
Fifth inning: Tommy Kahnle strikes out four batters
Sixth inning: Tommy Kahnle strikes out five batters
Seventh inning: David Robertson strikes out two batters, walks one
Seventh inning: Judge’s homer lands
Eighth inning: Dellin Betances strikes out six batters
Ninth inning: Aroldis Chapman walks three, strikes out three, as studio audience gasps, then applauds

How short can the Yankees make these postseason games? They can bring a closer-quality arm in from the fifth inning on if they’re willing to stretch one of them out for two innings. Heck, if they feel that two of those pitchers are good for a couple innings, they can essentially have a closer in the game from the fourth inning on.

That’s a mess for an opposing team, and the extra rest of the postseason will allow them to do it a whole bunch.

They just have to get to the postseason first.

So I’ll give them a provisional A, but the final grade will be reliant on how strong they make the team for the stretch run. The Yankees still have obvious holes and a dynamite farm system. The smart move is to target players who will help them now and in future seasons, like Kahnle, to minimize the hit to their farm system in the short term. Because this core is built to last a long time, and they’ll be the scariest four-inning postseason team in recent memory.

If they get to the postseason.

It’s about time the Yankees had something go their way, though. They’ve been quiet for way too long.