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Deal or No Deal: Will Cherington Open a Case Full of Trades?

by Emmet Mahon

Photo of Rich Hill courtesy of The Boston Globe.

There is less than two weeks until Major League Baseball’s annual trade deadline, August 1 at

6:00 P.M. Most attention between now and then will understandably be on the Anaheim Angels

and their otherworldly talent, Shohei Ohtani. There will be other deals of varying magnitude, but

one franchise guaranteed not to make any seismic transactions is the Pittsburgh Pirates.

The unexpected hot start by the Pirates had fans viewing this deadline as an opportunity for the

club to add talent that could hoist them to a post season berth. The sobering and epic collapse

that followed has fans recalibrating their expectations.

The Pirates do not have trade candidates that are high end talent with expiring contracts that

could fetch a handsome return. Any deal that General Manager Ben Cherington engineers would

result in complimentary or depth pieces. That does not preclude an acquisition that will provide

Major League talent. Last season’s deadline deal of pitcher Jose’ Quintana netted the Pirates

pitcher Johan Oviedo and infielder Malcom Nunez. Oviedo has already shown great promise this

season in the Majors. At age 25, there is still upside on an already evident tool set. Nunez, still

only 22 at AAA, possesses intriguing power. Though struggling in his first extended stint at

Indianapolis, and plagued by injuries, Nunez remains on the periphery of the Draft 412 Top 20

Pirates' prospects.

As rewarding as that low-key trade appears, it is an even lesser noticed trade that buoys fans'

hopes. The trade of Tony Watson to the Dodgers in 2017 at the deadline brought back a little-

known Class A shortstop by the name of Oneil Cruz. Not all trades turn out this well, but if even

one trade this year does, it will further their youth movement that they pivoted to weeks ago.

So, who might find themselves catching an Uber across the three rivers on the way to Pittsburgh


The most likely candidate is veteran pitcher Rich Hill. The fiery lefthander has qualities a

contender might covet to get them over the playoff threshold. First is his relentless competitive

spirit. Hill wants to win. Always. He wants his teammates to win. Always. This could lead to

uncomfortable dugout moments; however, those moments will be out of a desire to win. Hill will

give you all he has for every start. He will squeeze every pitch he has on any given day. So

dedicated to improving and competing, he recently added, at age 43, a split-fingered fastball to

his arsenal. His veteran presence will be helpful with young staff that find themselves in a

playoff hunt for the first time. A Hill trade could yield players similarly obtained in the Quintana

trade. However, the qualities that make Hill desirable to contenders could be useful to the

suddenly Young Bucs and minimize the growing pains they will experience in the season’s

closing months.

A team with post-season aspirations can always use a veteran presence on the field and in the

locker room. If that veteran is a switch hitter that provides premium defense, that is a player you

would like to graft onto your contending roster. Enter Carlos Santana. While his .230 average is

disappointing to some Pirate fans, it does represent an increase of almost forty points over his

2022 production. Santana is no stranger to playoff drives and high stakes playoff action. A

Santana trade could bring back two to three mid-level prospects that, if things break right, might

provide the Pirates with more talent throughout the system that might facilitate future


Two other players who have performed well below expectations, catcher Austin Hedges and

1B/DH Ji Man Choi, can be the type of players that a contender might acquire in hopes of

catching lightning in a bottle. The best that the Pirates could hope for in that scenario is lottery

tickets. If the prospect does not develop, then nothing of value was sacrificed. However, if that

prospect keeps on scratching and reveals three matching symbols, then jackpot! Like Hill, the

front office might view Hedges' mentoring ability to the young catching corps as more important

long term than taking a flyer on a kid that may never get out of the Dominican Summer League.

The name "David Bednar" is floating about the rumor mill as the piece Cherington could move for

a haul of prospects. In makes sense to consider it. Someone that can reliably close out games is

invaluable in the post season. While public relations should never be a consideration with any

transaction, moving hometown hero Bednar while the team is nosediving in the standings might

be too much to tolerate for even the most patient and loyal fans. The time to move Bednar is in

the offseason when Cherington will have twenty-nine suitors as opposed to a handful.

There is no way of knowing if any of these players might be part of a deal. However, the likeliest

deal would be prospect for prospect. The Pirates are facing severe roster crunches with their

middle infielders and pitching depth. The attempts to try middle infielders elsewhere has not

been pretty. The logical solution is to seek out teams with similar crunches at positions the

Pirates lack. Cherington would be wise to move his prospects blocked by better players in the

system. Other organizations may view them as upgrades over their current prospects. He should

seek outfielders, players showing power potential, or the ability to change innings around with

speed and superior base running. If any of those players can lead off and be table setters, that

would be a bonus. The never-ending revolving door at the top of the order needs to end


In the next week and a half, Pirate fans will be frequently visiting Twitter and sites like MLB

Trade Rumors to stay abreast of the latest news to see what Cherington has up his sleeve.

Consulting Baseball America and MLB Pipeline to evaluate future Bucco’s will occur. Armchair

GMs will exchange texts, emails and barstool conversations concocting the next big Pirates'

trade. It will be fun. More fun than they have had in the last few months.

Emmet Mahon can be contacted at

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