When Oakland’s Billy Beane and San Francisco’s Brian Sabean moved on to more senior, advisory positions in the past few years, Brian Cashman became the longest-tenured executive running day-to-day baseball operations for one team.
And it isn’t really close. Cashman became the Yankees’ general manager in 1998 and the next on the list is Texas’ Jon Daniels, who began in 2005.
In all that time – two decades and counting – Cashman has made trades of just about every type you can imagine: small, large, medium; for starters, relievers, sluggers. But you know what he has never done?
Obtain a prime-aged position player in his walk year before the non-waiver trading deadline — something that looks like Manny Machado.
In fact, he has never done it at any time on the calendar. The best position players he has traded for in the offseason, Alex Rodriguez and Giancarlo Stanton, were in the midst of what at the time were the largest contracts in major league history. Nick Swisher and Curtis Granderson also were acquired in the offseason. The best players close to their prime Cashman acquired in July, David Justice (2000) and Bobby Abreu (2006), also were in the midst of multi-year contracts.
Big-named players in their walk year obtained pre-deadline by the Yankees such as Ivan Rodriguez, Lance Berkman and Ichiro Suzuki were well beyond their primes. In recent years, the best of the walk-year lot have been Chase Headley (2014) and Todd Frazier (2017), and in the case of Frazier, he was the third piece in a trade and the White Sox insisted he be included for financial reasons.
During Cashman’s GM term, it isn’t like the landscape has been littered with elite position players still performing at or near their peaks who were traded during the season and before the non-waiver deadline. And it has become less frequent in recent years, with the best being Mark McGwire and Mike Piazza (1998), Scott Rolen (2002), Carlos Beltran (2003), Nomar Garciaparra (2004), Carlos Lee (2006), Mark Teixeira (2008), Matt Holliday (2009), Yoenis Cespedes (2015) and J.D. Martinez (2017).
In most of those seasons, the Yankees had a strong position group and no urgency to dabble — a case you could make as the 2018 non-waiver deadline approaches July 31 at 4 p.m.
Cashman — like all seasoned negotiators — attempts to create leverage by convincing the other side he is not feeling huge pressure to do a deal. When he actually has that leverage, Cashman has followed a similar path to acquisition. Namely, he makes offers he can tolerate then lets the ticking clock work, and if teams have nowhere else to go, they often turn back to the Yankees. This is how the Yanks landed Abreu and Stanton, for example.
The Orioles pretty much must trade Machado in the next two-plus weeks. He is in his walk year, Baltimore is not going to re-sign him, and the Orioles can do better than a compensation pick after the first round of the 2019 draft, which is all they would receive by giving him the qualifying offer and having him sign for more than $50 million elsewhere as a free agent. But because the Orioles held Machado to his walk year, his value has dropped below his talent. Teams have generally become more hesitant to include blue-chippers for a rental, particularly a positional rental.
But with several teams such as the Brewers, Diamondbacks, Dodgers, Yankees and others involved, the Orioles will attempt to play one against the other to improve offers.
Even in these situations, particularly as Hal Steinbrenner’s ownership has become more entrenched, the Yanks have been rare to blink.
My gut on where the Yankees are right now is this: They are coming to peace that the high-end starter they crave and would pay lavishly for is not going to be available. For protection and depth, they will still almost certainly obtain a starter from the Michael Fulmer, J.A. Happ, Lance Lynn, etc., bin.
Without the ace type, the Yanks will also prioritize protecting the rotation even more by adding another high-end reliever to what already is arguably the majors’ best pen. The Yanks will look to shorten games with every starter not named Luis Severino.
Therefore, it is possible if the Yankees trade with the Orioles, it would be for Zach Britton.
But that doesn’t mean it is impossible they land Machado. No one saw the Yanks coming for A-Rod, and they were mostly bystanders for Stanton until a week before the deal. However, if Cashman’s history is the guide, he will make an offer then wait to see if the market collapses and the ticking clock toward a deadline motivates a must-act team back to the Yankees.