Skip to main content
Come Fan with UsSaturday, June 20, 2026

Yankees trade for Chase Headley, should stop there

Despite myriad injuries and disappointing performances by veterans, the Yankees have hung in the AL East race. While they still have a chance to win a weak division, they need their prospects more than a shot at the title.

How is it the zombie Yankees aren’t dead yet? Usually it’s not good writing form to just let a question hang like that, but I’m guessing that someone somewhere will read this and think, “The indomitable spirit of the captain, Derek Jeter,” and I don’t want to deprive anyone who believes that of their right to a mystical faith in super-heroes. After today’s trade, that same hypothetical reader might also have gained a mystical faith in former Padres’ third baseman Chase Headley. That reader would be equally wrong on both counts.

It’s not that, though. Jeter may very well be having the best season in the history of 40-year-old starting shortstops, but that’s damning him with faint praise and according him a purely mythological status: The only reason he’s a starting shortstop is because the Yankees say he is, or because a farewell tour may be as financially valuable as winning a pennant. As for Headley, he was the right kind of acquisition, a buy-low short-timer on his way to free agency who the Padres actually sent cash to pay for while costing the Yankees merely a utility type in Yangervis Solarte and a 23-year-old High-A pitching prospect in Rafael De Paula, who throws hard but whose future likely lies among the International Relievers Benevolent Marching and Chowder Society. Barring further trades of this nature, the Yankees should stop there.

At this writing, the Yankees are 50-48 and in a statistical tie with the dying Toronto Blue Jays for second place in the soft AL East. The Orioles currently lead, but they’re on an unimpressive 89-win pace. If the Orioles’ stay on that pace, the Yankees would have to play .625 baseball the rest of the way to overhaul them. That’s a 101-win pace over a full season. It’s not impossible -- teams have gotten hotter than that over short spans of time -- but in their case seems especially unlikely. Baseball Prospectus’s playoff odds give them a mere 22 percent chance of playing into October. ESPN gives them a 16 percent chance.

And yet, and yet, if you just squint a bit, you can almost see it happening, see the beating heart beneath the zombie veneer. First, the projected record is a bit distorted by the nature of Yankees' losses. The Rangers and Rockies have each had 10 games in which their pitchers have allowed 10 or more runs. The Phillies and Astros have had nine such games (I initially mistyped that as "suck" games, which I probably should have left), and then next comes the Yankees and the White Sox with eight 10-run games apiece.

That would normally suggest the obvious, a bad pitching staff, but there are some extenuating circumstances here. Of those eight disaster games, two were started by Ivan Nova, who is broken and can no longer affect things, three were begun by Vidal Nuno, who is now the Diamondbacks' problem, for good or ill. Two blowouts were started by Hiroki Kuroda, but Kuroda has seemingly righted himself -- he's made nine starts since the calendar turned to June and put up a 3.10 ERA in 58 innings. The remaining 10-plus game belonged to David Phelps, who has made three consecutive quality starts and, at the risk of picking arbitrary endpoints, has been solid in six of his last seven appearances.

So, the Yankees rotation that created that negative run differential is now dead. To quote John Cleese, it has ceased to be; it has shuffled off this mortal coil. The downside of this is that pitchers who contributed to the positive aspect of it, especially Masahiro Tanaka, are also dead. Michael Pineda and his 1.83 ERA are slated to come back in August, but as is always the case with Pineda the questions are (1) "Are you sure about that?" and (2) What kind of pitcher will he be after yet another round if idleness and possibly-debilitating injuries?

The current Kurodaettes currently include Brandon McCarthy, who has been great so far, and away from the Diamondbacks he might stay that way, albeit not at a 1.42-ERA level. Shane Greene has been solid, with intriguing stuff -- right-handed hitters have struck out about a third of the time against him (he allowed four runs in 5.2 innings on Monday but might have gotten away with two had runners he bequeathed to Matt Thornton been stranded). Chase Whitley, the converted reliever, probably needs to be converted back, but perhaps Pineda will take his place in a relatively short period of time. If you want to look at the Whitley glass as half-full, he hasn't been any worse than CC Sabathia was.

Brett Gardner and Ichiro Suzuki. Yankees outfielders have combined to hit only 25 home runs. (Photo credit: Robert Deutsch-USA TODAY Sports)

At the same time, the reasons for pessimism seem obvious. If you just take a surface look at the stats, the Yankees don’t seem to deserve to be where they are now. Their projected record based on runs scored and runs allowed is only 46-52. The Yankees also haven’t hit much -- their OPS+ is only 92, and despite hitting in a home-run-happy ballpark are just ninth in the league in that category. They’re also ninth in batting average and 11th in both on-base percentage and slugging average.

It takes a starting rotation to make it, and as has often been pointed out, Kuroda is the last man standing from the Opening Day rotation. On Thursday of last week, Yankees general manager Brian Cashman said in a telephone interview with ESPN’s Andrew Marchand that the Yankees “have to try to improve, reinforce and upgrade” their pitching. When your starting rotation going forward is Kuroda, McCarthy, Whitley, Greene, and David Phelps, you’ve not only struck an iceberg and are taking on water, you’ve sunk.

Naturally, the first move was for a third baseman instead. Headley is a nice upside play; if he can get back to being the player he was prior to last year, the switch-hitter will help the Yankees add some of that needed pop ‘n’ patience from the left side, and his defense at the hot corner should be a plus regardless. Yet, as Cashman’s water-is-wet statement correctly states, the team’s melange of post-A-Rod third baseman was hardly its biggest problem.

The breakdown of the starting rotation, particularly the loss of Tanaka, is the bigger issue. The good news is, the Yankees don’t have to replace him at the same level, because while it’s nice to have Christy Mathewson or Pedro Martinez in your starting rotation, it’s such a long fall from there to the average pitcher that it leaves plenty of room for some acquisition to be simply competent. In other words, you don’t need Tanaka II, you just need the next guy to be better than Whitley, assuming all else remains equal.

... Which you can’t assume. Pitchers are fickle. A long, long time ago, the Yankees had a right-handed starter named Hank Borowy, who had been very good for them, but midway through the 1945 season, for reasons that seem bogus even knowing the baseball culture of the time (the proffered explanation was he hadn’t pitched enough complete games) the then-ownership put him on waivers. Somehow no AL team bit and he wound up with the Cubs for the $100,000 waiver price. Once in Chicago, he went 11-2, won the NL ERA title, and pitched the Cubs into the last World Series that franchise has seen. Once there, the Cubs’ manager, Charlie Grimm, went insane and somehow maneuvered Borowy into taking four decisions in a seven-game series, pitching him in Game 1, on three days’ rest in Game 5, in relief on no rest in Game 6, and started him again on one days’ rest in Game 7.

Hank Borowy (center) in 1945 (Photo credit: Getty Images)

As Grant Brisbee wrote on Monday: Cubs.

The Cubs would one day repay the Yankees by trading them Steve Trout for three pitchers, one of whom turned out to be Bob Tewksbury. The Yankees would have been better off sending the players home for the season, burning Yankee Stadium, and collecting the insurance money, but strange good things can happen with pitchers as well: see McCarthy right now (perhaps), or the random role of the 20-sided die that was Aaron Small’s 10-0 2005 season, or that Edinson Volquez has a 2.52 ERA in his last six starts for the Pirates. We’re not meant to understand.

When it comes to bolstering the rotation, then, anything can happen. The problem is that whatever the Yankees need, whatever the availability of Cliff Lee (at the risk of judging from one start, “trading for Cliff Lee” may not mean the same thing it used to), the Yankees cannot trade. The reason they went 85-77 last year is the same reason they’re struggling to about the same record this year except with a more expensive pile of 30-and-over mercenaries: They have done an exceptionally poor job of drafting and development (and don’t use the “the always win so they have bad draft position” excuse; somehow that doesn’t apply to the Red Sox). As the old guys have failed or gotten hurt, they have had no internal replacements.

That’s less true than it used to be, but not as a function of time. That is, they recovered some good-looking prospects from the 2013 amateur draft, players such as third baseman Eric Jagielo, outfielder Aaron Judge, and left-hander Ian Clarkin. Some lesser prospects have had decent years as well. Few of them are ready, though, or are in line for the positions at which the Yankees need the most help. If they deal for a Lee or a John Danks (rumored today, and woof -- Danks may have hit his sell-by date four or five years ago, is owed $28.5 million over two more seasons, and a home-run happy pitcher in Yankee Stadium is a bad fit, left-handed or not), that would mean drawing from the 2013 pile, and that in turn would perpetuate the cycle of superannuated old guys signed to contracts that last far longer than can be productive.

In short, they’d be where they are now, but worse off, and with no guarantee that any acquisition they can make would make them a good bet to win it all.

It says above that it’s better to have an arm and a dream than a dream alone. In this case, barring an exceptionally cheap pickup (the White Sox might be willing to give Danks away at this point, and whereas you get what you pay for, at that point what the hell) it might be smarter to just go with the dream, hope that a ragtag, fugitive fleet of arms (to borrow from the old “Battlestar Galactica” closing narration) can get the job done in a year when the division is wide open. Think not of domination, but of the 1973 Mets, an 82-win team that made it to the seventh game of the World Series.It’s a tenuous hope for the present but would make for a better future.

See More:

More in MLB

MLB
Oklahoma-Georgia gave us an incredible family moment at the Men’s College World SeriesOklahoma-Georgia gave us an incredible family moment at the Men’s College World Series
MLB

Kolby Branch’s final collegiate swing capped off a bittersweet night for the Branch family in Omaha

By Mark Schofield
MLB
Men’s College World Series 2026: Schedule, scores, and how to watchMen’s College World Series 2026: Schedule, scores, and how to watch
MLB

Here is everything you need to know about the 2026 Men’s College World Series, from the full schedule to how to watch

By Mark Schofield
MLB
Owen Hull and UNC knock off West Virginia to advance to the MCWS FinalsOwen Hull and UNC knock off West Virginia to advance to the MCWS Finals
MLB

UNC is headed to the Men’s College World Series Finals after knocking off West Virginia in Omaha

By Mark Schofield
MLB
Men’s College World Series: Joey Volchko dominates as Georgia knocks off TexasMen’s College World Series: Joey Volchko dominates as Georgia knocks off Texas
MLB

Georgia’s Joey Volchko was dominant as the Bulldogs knocked off Texas to open their MCWS

By Mark Schofield
MLB
Men’s College World Series: Gavin Gallaher, Colin Hynek deliver for UNC vs. Ole MissMen’s College World Series: Gavin Gallaher, Colin Hynek deliver for UNC vs. Ole Miss
MLB

Gavin Gallaher’s first career MCWS hit came at a perfect time for UNC against Ole Miss

By Mark Schofield
MLB
Men’s College World Series 2026: One key player for each teamMen’s College World Series 2026: One key player for each team
MLB

Here is one key player to watch on each team at the Men’s College World Series

By Mark Schofield