It’s that time again, when Prospectus staffers assume the role of general managers for the sake of entertainment (and embarrassment). This time around, 10 writers made their best pitches to secure the services of Padres outfielder Justin Upton. Here are the actors and their characters:

Terry Ryan (Twins) – Dylan Schultz
Brian Cashman (Yankees) – Jon Shepherd
Bobby Evans (Giants) – Al Skorupa
Sandy Alderson (Mets) – Chris Mosch
Jeff Luhnow (Astros) – Dan Rathman
Jed Hoyer (Cubs) – Chris Crawford
John Mozeliak (Cardinals) – Rian Watt
Neal Huntington (Pirates) – Ian Frazer
Dayton Moore (Royals) – Kate Morrison
Chris Antonetti (Indians) – JJ Jansons

And the star of the show: Geoff Young is playing A.J. Preller.


As you know, our goals this year were twofold: to ignite fan interest in the Padres and to bring a contender to San Diego. We succeeded on the first count by adding players with name recognition to our roster but still have work to do on the second.

Upton, one of the many new players acquired over the offseason to help us reach our goals, is a free agent after 2015 and is much coveted by those that aspire to win the World Series. As we sadly no longer fall into that category, Upton’s value to the Padres now lies more in what he can fetch in trade than in what he can accomplish on the field.

We were aggressive over the winter with an eye toward competing right away, and although the results have been disappointing, we remain committed to that vision. This is not a rebuilding job.

With this in mind, while we intend to maximize our return on Upton in any trade, we are most interested in players who can contribute immediately at the big-league level. Those who have yet to reach Double-A may be exciting but are not what we are targeting.

Our top priorities, in descending order of importance, are to add

  1. a shortstop who provides a more viable short- and long-term solution than some combination of Alexi Amarista and Jose Rondon;

  2. a center fielder who can play center field;

  3. a power-hitting third baseman who is not another Will Middlebrooks; and

  4. pitching depth.

We cannot address all of these needs but are confident that a player of Upton’s caliber will bring back something of value in at least one of these areas. Let us turn to the offers.


From: Brian Cashman
To: A.J. Preller

Hey A.J.,

Let’s cut this short. The Brian wants Justin Upton and Andrew Cashner. Why? Your job is not to understand the Brian. Your job is to accept what I offer and be a winner.

Your middle infield is garbage. Trash. Take Jorge Mateo. Great runner, gives pitchers headaches. Good bat, good glove. He will take over shortstop for you in a couple of years.

Your center field is garbage. What is out there now? Literally garbage. The Brian will gift you Jake Cave and you will thank The Brian. He won’t be an All-Star, but he is not garbage. Adequate center fielder with adequate speed. Bat works and is better than garbage.

Your first baseman is garbage. The Brian has gotten six times as many home runs out of his second baseman than you have from first. Just take Greg Bird. Take him. Strong, bat-first player. You can thank The Brian now.

So be a winner. I am sending Mateo, Cave, and Bird on my private jet to San Diego. Upton and Cashner better be here on the return flight or you will hear from me in court.

–The Brian

From: A.J. Preller
To: Brian Cashman

Dearest Brian,

It is so wonderful to hear from you during these difficult times in San Diego. As you know, our plans for the summer did not unfold in the precise manner that we had envisioned, and your humor is well received as we strive to set our proud house in order. I am especially pleased at your mastery of the word “garbage” and am grateful to see by the names you have offered in trade that my beloved Padres are not alone in possessing such. Your proposed package of Mateo, Cave, and Bird amuses me to the point that my melancholy has disappeared. Thank you ever so much for that generous gift. As for the rest, court sounds lovely. Two-on-two according to the usual fashion? I shall fetch Will Venable, and we will engage in a rousing game of hoops.

Warmest regards,



From: John Mozeliak
To: A.J. Preller

Hi A.J.,

Hope you’re well. Understand you’re hoping to put something together for Upton that’ll set you up for a relatively quick turnaround in 2016. We like him for this season (the Pirates aren’t getting any further away) and want to make sure we’re in a good position to make a run at him longer term if Jason Heyward proves difficult to re-sign in the offseason.

I’ve got two packages I can offer you: Jon Jay + Tim Cooney, or Peter Bourjos + Sam Tuivailala. In either case the headliner would fit nicely in your outfield this season (despite Jay’s current injury) and is already signed through next season. Cooney and Tuivailala we both like a lot, and they can step into your rotation or bullpen, respectively, as early as next year. Let me know. Looking forward to this conversation.


From: A.J. Preller
To: John Mozeliak

Dearest John,

Your concern for my well being is touching, and I might inquire the same about you, hoping of course for an affirmation that all is well. Regarding the business at hand, Bourjos and Tuivailala would fit our needs quite nicely, not only because of their mellifluous monikers but also because we need outfielders who can cover more ground than a hen needs to lay eggs and because there is an emptiness in my heart that only a hard-throwing right-hander can fill.

Yours faithfully,



From: Jeff Luhnow
To: A.J. Preller


Hope all’s well in San Diego.

Since things haven’t gone as planned in your first season out west, we’d like to acquire Justin Upton to upgrade our outfield at the expense of a few players who could improve your outlook in the near future.

Our offer: OF Domingo Santana, LHP Josh Hader, and RHP Francis Martes


From: A.J. Preller
To: Jeff Luhnow

Dearest Jeff,

Your extreme terseness can only be described in fewer words than I have to spare. I cannot imagine what I may have done to deserve such harsh treatment from you, but I can say that although Santana intrigues us, he would intrigue us a great deal more if he played center field.

Thank you, and good day.


Mr. A.J. Preller


From: Terry Ryan
To: A.J. Preller


Let’s not beat around the bush: You’ve got a team that has a very small, if any, chance of making the postseason. Justin Upton is burning a hole in your payroll to the tune of $14.7 million and he’ll likely go elsewhere in free agency in 2016. You’re looking to build your team for the future; I’m looking to boost my offensive production and make a run at the World Series for the first time since 2010. Let’s make a deal.

In terms of what you need to feel compensated for losing Upton, I believe your organization lacks pitching talent for the future. Ours has a plethora of young exciting arms. I’m offering to exchange Justin Upton for Alex Meyer and Stephen Gonsalves. This pairing of arms gives you high-upside prospects for both the near and mid-range future. Let’s make this work.


From: A.J. Preller
To: Terry Ryan

Dearest Terry,

We are agreed that beating around the bush would be best avoided if possible. This is a promising start. Also promising is your inclusion of the name Meyer in these discussions. Although our primary needs are on the infield, Meyer would look wonderful in our rotation now and into the future. I cannot ignore that, nor the fact that Gonsalves is a San Diego product who would be welcome here at home. You tempt me most wickedly, mon ami.

Yours very truly and devoted,



From: Sandy Alderson
To: A.J. Preller

Hi A.J.,

We’ve had a rough go of it since the break but still feel like with the right upgrades on offense we can make a run at a playoff spot this year. We like Upton and feel like Will Venable could make for a good platoon with Juan Lagares in center for the rest of the year, but we’re also looking to make a deal that helps us for next year. So here’s our offer: Michael Conforto, Gavin Cecchini, and Bartolo Colon for Upton, Andrew Cashner, and Venable.

I know your farm system took a bit of a hit after all of the moves this past offseason. Adding Conforto helps you replenish the system and gives you a young player to build around for the future. Plus, he can step in at the big-league level right now if you want. We really like the steps Cecchini has made this year at Binghamton and he should be a solid infield piece for you in the future, even if he eventually has to move off shortstop. To be completely honest, I needed to get a little bit of cap relief in order for ownership to sign off, so for this to work I’m going to need you to take Colon. But he’s a great guy in the clubhouse and the fans goes nuts whenever he starts and gets to hit, so it’ll help make the last two months a little more fun even after having to sell at the deadline. Let me know what you think.



From: A.J. Preller
To: Sandy Alderson

Dearest Sandy,

I am honored by your offer of a bat-first left fielder, an offense-challenged utility infielder, and a 42-year-old pitcher for our best hitter, one of our best pitchers, and a great two-on-two basketball partner (I understand and respect your desire to be reunited with Venable, whom you drafted) but must respectfully decline at this time.

Always and forever,



From: Dayton Moore
To: A.J. Preller

A.J. –

We’re willing to send you former first-rounder Sean Manaea, former first-rounder (and Texan!) Hunter Dozier, and shortstop Orlando Calixte for outfielder Justin Upton.

All of this talent is currently in Double-A, perfectly positioned for when you inevitably complete your rebuild of that storied franchise. Yes, it hurts to send away three first-round picks, but we need an outfielder, and you need high-level talent in your farm system. Dozier’s bat hasn’t shown particularly well his first turn through the Texas League, but we believe it will play, and having an actual infielder to come up and play third base will be nice. Also nice, for you, is having a shortstop prospect; Calixte is that. Only 23, in Triple-A, and would probably be better in the majors for you than who you’re currently having to run out there. He’s a slick fielder, and the bat, while not exciting, should play better in the future than the line looks right now. Plus, next year you’ve potentially upgraded your infield by quite a bit while only losing a rental.

Sean Manaea’s the kind of pitcher that if things go well, we’ll look really bad in two years for giving him up. He’s possibly farther away from the majors than the other two, but 2016 isn’t your year, is it? You’re going to go head-to-head with the Astros in the 2017 World Series, if Sports Illustrated is to be believed, and Manaea could be your Game Two or Three starter. It’s all about the long game, yes?

Think about it, look forward to hearing back,


From: A.J. Preller
To: Dayton Moore

Dearest Dayton,

Your offer is quite compelling. Manaea’s injury history rightly concerns us, but the promise of a front-line starter is simply delightful. Dozier’s status as one who hails from Texas is almost enough to offset the resemblance of his statistical line to that of the last third baseman from that state we acquired, the strikingly strike-zone challenged Mr. Middlebrooks. As regards Calixte, we love his name and defensive ability but do not believe he represents a significant upgrade at shortstop from our current modest choices. Dozier and Calixte appear to be future bench options, which means that we would need Manaea to develop as hoped to make this work. As I said, it is a compelling package, and I thank you for your consideration.

Fare thee as well as I fare,



From: Chris Antonetti
To: A.J. Preller

Dear A.J.,

I’d like to get something done quickly, as in before the gel in your magnificent hair dries, so I’ll get to the point. You need infielders and I happen to have a few extra ones in Columbus. It’s not that we don’t like our guys currently at Triple-A—we do, we really do—it’s just that we like Giovanny Urshela and Francisco Lindor better.

We sent Jose Ramirez down at the beginning of June and he’s done nothing but hit since. He might not be as sexy a name as some prospects you’ve been offered, but you mentioned that acquiring a shortstop was at the top of your priority list and you’d be getting one that doesn’t turn 23 until September and owns a .300-plus average in the minors. I don’t have to tell you how valuable that is.

We also will send Lonnie Chisenhall your way. He could be everything Will Middlebrooks wasn’t for you. Dace Kime is a guy we’ve discussed before, and we’ll send him your way if we can get this done today. Time is running out on our season and if we’re going to do something, we need to do it now or we’ll just hold onto these guys until the winter.


P.S. I’m sure the Upton brothers have enjoyed playing together the last few seasons but that’s not happening here. Thanks though!


From: A.J. Preller
To: Chris Antonetti

Dearest Chris,

Thank you so kindly for remembering my hair. It seems like only yesterday that everyone was talking about it, but now that I am the longest-tenured general manager in the National League West, they only want to discuss baseball matters. Ah well, such is the way of the world. As regards the players you graciously mentioned, Ramirez could be of some use, although we are not convinced that his arm will allow him to remain at shortstop nor that he represents a significant upgrade from our current options. Chisenhall would be magnificent, particularly if you can send us the 2014 version and not the gentleman who wore his uniform before and after that. Kime has a wonderful name, and I am glad that you included it in your offer so that I could delight in it.

All the best,


P.S. Why do you hate brothers?


From: Jed Hoyer
To: A.J. Preller

Hi, A.J.,

Long time no see. Hope you’re enjoying San Diego, I hear they have good everything.

So, I know you guys have been playing a lot better lately, but I also know that you have two teams ahead of you in the standings and that you’re a smart guy, so I’d like to see if I can acquire one Mr. Justin Upton from you.

Our offer is. Billy McKinney, Dan Vogelbach, and Corey Black. I know that you know that I know that you know that you like guys who have a natural feel for hitting, and in McKinney and Vogelbach, you’re getting two young players who have exactly that.

McKinney possesses a plus hit tool—some on my staff argue it has a chance to be plus-plus—and while he’s not going to win any Gold Gloves in the outfield, he’s not someone you’ll have to replace late in games. The power is still developing, but if you give it time, he’s a perfect no. 2 hitter in your lineup for the next decade.

Yeah, Vogelbach can’t play defense. Yeah, he’s slower than us. But man, this kid can really hit. He’s 22 and he’s already getting pitched around. There’s a chance for two 60 tools here, and worst comes to worst, he’s great motivation for establishing the DH in the National League.

Black is a guy who we think can help our bullpen for a long time, but if it means we can get a bat like Upton in our lineup, we’re willing to sacrifice a little bit. The fastball is plus-plus—routinely in the high 90s—and the slider is pretty nasty, too. Maybe the command keeps him from closing, but you have Craig Kimbrel; you don’t need a closer. Ever.

This is two elite offensive prospects and a high-leverage reliever for a guy you lose in two months. I look forward to you saying yes.


Theo … I mean … Jed. Yeah. Definitely Jed.

From: A.J. Preller
To: Jed Hoyer

Dearest Jed,

You send my heart fluttering with names such as McKinney and Vogelbach. To dream of what they might accomplish at the plate … And yet, when I wake, I am reminded that dismissal of defensive aptitude helped create this somber situation in San Diego. I would hope that I have learned from experience to refrain from fielding a team full of well-intentioned gentlemen who do not know how to properly use a baseball glove. Thank you, but I fear we cannot make this trade.

Yours most humbly affectionate,


P.S. Give my regards to Theo. I do hope he is well.


From: Neal Huntington
To: A.J. Preller

Hey A.J.,

I’m sorry that your offseason transaction spree didn’t work out. I swear, I thought you had an explosive charge in your chest that would explode if you didn’t make a trade, like Jason Statham in Crank. But I know how you can get that tasty trade buzz again: by making a deal with us. I mean, this would all be contingent on you convincing someone to move from San Diego to Pittsburgh, but I’ll leave that to you. I mean, our ballpark’s nice! And you can still get Ballast Point out here!

Here’s what I’ll offer: Gerrit Cole. Hah, just kidding, I’d give you my left nut before I gave you him. The deal with us is that we’re a tad thin, depth-wise, in the majors. It’ll have to be prospects. I see that your infield, especially the middle part, is in desperate need of somebody, anybody, right now. I’ll give you Alen Hanson, who profiles more as a second baseman right now due to lack of polish and consistency but who could fill in at short or even stick there with a little refinement. The bat’s ready; he’s hit at every minor-league level, and could come up for a cup of coffee at the end of this year.

I’ll also give you Cole Tucker, our first-round pick from last year. He’s a tall, rangy kid who has the actions, range, and arm to stick at short, or possibly transition to the outfield if needed. The body’s still lean and he’s still working on developing usable power, let along tapping into it. But the contact ability and feel for the barrel is there, and makeup-wise, there’s nothing to worry about.

From: A.J. Preller
To: Neal Huntingdon

Dearest Neal,

Oh, you wicked man, such a trickster teasing me with promises of Gerrit Cole. My heart skipped a beat before I realized you spoke in jest. So cruel! Regarding your actual offer, the description of Hanson sounds suspiciously like that of several players currently in our organization. And while depth is always appreciated, we are more interested in players who can make an impact on something more than a big-league bench. The other man you mentioned, young Mr. Tucker, might be such a player. However, he only just turned 19 years old. Given our intention to contend sooner rather than later, I am not sure we can wait three or four years to find out what he might become. Also, you are cruel.

Farewell most heartily,



From: Bobby Evans
To: A.J. Preller


Definitely have interest in Justin Upton. He’d be a nice fit for our lineup and I’ve always thought his game would play up in our ballpark. He’s not an ideal match for what we like, but I think it will work and add another dimension to our team.

In that spirit, I’d be willing to part with Kyle Crick, Clayton Blackburn, Chris Stratton, and Ehire Adrianza for Upton and Clint Barmes. You add three upper-minors arms who can help soon. You’re going to be parting with more pitching soon, and this deal would allow you to add some solid near-ready arms to build with and ensure you don’t lose 100 games next year. You can also get cheaper at utilityman with Adrianza for the next couple years. He’s a 0–3 guy with big-league experience who will fit on your bench.

Let me know what you think.


From: A.J. Preller
To: Bobby Evans

Dearest Bobby,

Oh, you know me so well. Crick has the type of arm that makes me want to stand up and sing. I want to fill the air with melodies attached to poetry: “Hail Crick, admire how hard the ball he throws, if only he learned to control where it goes!” Blackburn may not inspire song but he does throw strikes, which I also like. He could well replace Ian Kennedy in next year’s rotation, and probably surrender fewer home runs in the process. And we will find a use for Stratton. As for the infielders, Adrianza has a wonderful name, and Barmes is not the key to our future. Three big-league-ready pitchers from a division rival is most tempting indeed. You honor me greatly with your generous proposal.

Respectfully yours with sincere gratitude,



These decisions are never easy. The heart battles the mind, and I grow weary. In some respects, choosing to part with Upton is the hardest part. In saying farewell to him, we say farewell to the promise of a dream that never became reality.

But life is ever changing, and where one dream yields another takes its place. And we believe that the players acquired for our dear Mr. Upton will help bring a championship to San Diego and its fans who have waited so patiently for their day in the proverbial sun (their day in the actual sun having come long ago and seldom departed since).

In the end, there were three possibilities that seriously tempted us. First was the Royals’ offer of Manaea, Dozier, and Calixte. The two infielders are not quite the caliber we had hoped to land, which is hardly surprising given Upton’s impending free agency. But they do provide some utility, with a chance at more. Coupled with Manaea’s high-risk/high-reward profile, this was a compelling package that could help us right away and into the future. However, the risk with Manaea was too high, while the potential reward with the others was not high enough to offset that risk.

The second offer we gave careful consideration came from the Twins. It did not address our primary needs but did address a secondary one: pitching depth. And more than just depth, their package of Meyer and Gonsalves would have provided us with impressive upside for a rental. This one was very difficult to turn down, but ultimately it fell short of the one we could not refuse.

The trade we ended up making was with the Giants. Although Crick is arguably a higher risk than Manaea and Meyer, his potential is still enough to make this worth our while. Even as a reliever, he fits the mold of others I have acquired in the past, namely Brandon Maurer and Shawn Kelley. If we can get Crick to throw strikes, I like his chances. He will continue to refine his approach at Triple-A for now and should see time with the big club in September.

Blackburn and Stratton may not be as exciting, but they will contribute next year, if not sooner. Blackburn immediately slots into our rotation, replacing Odrisamer Despaigne. As for Stratton, he will remain at Triple-A for the time being. Like Crick, he could get a cup of coffee when rosters expand. Both Blackburn and Stratton will be a part of our 2016 rotation.

We believe that the Giants provided the strongest overall package in return for Upton. However, in the interest of full disclosure, I must admit that taking those resources away from a division rival played a role in our decision to accept their offer over similarly worthy packages.


From: A.J. Preller
To: Bobby Evans

Dearest Bobby,

Your assessment of our needs and the market was flawless. I do, indeed, love power arms. And your offer was, in fact, the best of all those we received. It is therefore with great pleasure that I accept your proposal to send us Crick, Blackburn, Stratton, and Adrianza in exchange for Upton and Barmes. Best of luck to your Giants of San Francisco, and I hope we can do business again in the future.

Very respectfully,