Let’s take J.A. Happ as the kind of starter the Yankees will fixate on as the trade deadline approaches.
As opposed to, say, Jacob deGrom, Happ is going to be traded in the next five weeks. Toronto is run by executives who look at the game from 20,000 feet, and what Mark Shapiro and Ross Atkins see is an AL East landscape in which the Red Sox and, especially, the Yankees will be ascendant for at least a few years.
Thus, the best counterattack is to build a substantial young talent base and then augment with money. In third baseman Vladimir Guerrero Jr. and shortstop Bo Bichette, the Blue Jays have two of the game’s elite prospects. Meanwhile, Toronto will remove its three largest contracts after this year (Josh Donaldson), next year (Russell Martin) and the year after (Troy Tulowitzki).
Before the season, Donaldson and Roberto Osuna were viewed as the main July 31 trade chips. But Donaldson has failed to stay healthy or familiarly productive while Osuna is now in the midst of a 75-game suspension for violating MLB’s domestic abuse policy — a ban that carries beyond the trade deadline.
That leaves Happ, concluding a three-year, $36 million pact, as Toronto’s most valuable trade asset. So what can the Blue Jays get for him?
The most similar thirtysomething lefty starters recently traded at the deadline in their walk years were Scott Kazmir in 2015 and Rich Hill in 2016 — both by Oakland. Kazmir and Hill — like Happ — had enjoyed a later-in-career rise. At the time they were dealt, Kazmir and Hill had a better ERA-plus and Win Above Replacement in those seasons than Happ is taking into his Monday night start against the Astros.
Kazmir went to Houston for catcher Jacob Nottingham and starter Daniel Mengden. Hill went along with Josh Reddick to the Dodgers for three pitchers: Jharel Cotton, Grant Holmes and Frankie Montas. It could be assumed Hill would have fetched two of those pitchers by himself.
In fact, walk-year starters recently have brought back mainly pitching, whether it was high-end types such as Johnny Cueto or David Price, or someone lesser such as Jaime Garcia, who was traded twice last July for three pitchers in all. Yu Darvish was the rare walk-year starter whose main piece back was a position player (Willie Calhoun).
A Happ-level starter in his walk year has basically returned two good, but not elite starters. The Yankees will not be alone in trying to land Happ if he is arguably the best starter available. But the way the Yankees are structured gives them ammunition. For their area of organizational depth is now pitching.
Plus, Brian Cashman has in recent years used trades, including at the deadline, to preemptively address 40-man roster issues. The pruning has left the Yankees looking at less clutter this coming offseason. Except for one area: starting pitching.
Chance Adams, Josh Rogers, Justus Sheffield, Erik Swanson and Dillon Tate must be put on the 40-man roster this offseason or be vulnerable in the Rule 5 draft, and all but Tate (at Double-A) are already at Triple-A. Prospects Albert Abreu and Domingo Acevedo were added last offseason. The Yankees also must have on their 40: Luis Severino, Masahiro Tanaka, Sonny Gray, Domingo German, Jordan Montgomery (who in the offseason has to be put back on the 40-man from his current 60-day DL designation), Jonathan Loaisiga and Luis Cessa.
It is unlikely the Yanks go into the offseason with all 14 of those starters on their 40-man roster and have enough room for everything else they need to do.
Unless it is for a starter such as deGrom, the Yanks would not make Sheffield available and would be hesitant with a few others such as German or Abreu. They do have positional depth at Triple-A with Brandon Drury, Clint Frazier, Billy McKinney and Tyler Wade. But pitching might be easier for them to dole out because they believe they have a group emerging, headed by Luis Medina, that does not yet need to be placed on the 40-man roster.
So if the Yankees try to land a starter such as Happ and/or a lefty reliever such as San Francisco’s Will Smith or Tony Watson, I would suspect part of the deal would be starters either on the 40-man roster now or who need to be protected come this offseason.
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