In the new era of hard slots and caps on amateur spending, every win by a bad team after the trade deadline actively hurts the franchise. That’s one reason why it was surprising and disappointing to see the Padres and White Sox pass on trading away their impending free agents at the end of July. It was a gross and costly error in judgment for both teams, because neither is a real playoff contender, and only optimism raised to a pitch of delusion could have convinced them otherwise. They missed chances to trade valuable short-term assets for longer-term ones, and in so doing, they also retained talent that will make it harder for them to play badly enough down the stretch to achieve the draft position that should be their goal at this point.

August, of course, gives second chances. Some players’ trade value is totally quashed by the waiver process, but the qualifying offer system has preserved the leverage of the would-be seller even in August, at least for players good enough to be considered real candidates for an offer. The Padres have just one of those, really: Justin Upton. The White Sox have one, too, in Jeff Samardzija. In each case, though neither player would make it through waivers, the team trying to trade them can present the claiming team with the following ultimatum: make it worth our while, or we’ll just keep the guy.

Specifically, of course, “make it worth our while” means “give us more than the value of the compensatory pick the guy can get us this winter.” That value is easy enough to estimate, given the flurry of competitive-balance picks we’ve seen dealt over the last two years. So the real questions are:

  1. Which teams are most likely to claim each of Upton and Samardzija? and

  2. Could (or should) those clubs give up enough to wrest the players away from their current homes?

Let’s take them one at a time.

Justin Upton

2015 Stats: .255/.337/.447, .303 TAv, 2.8 WARP
Remaining Salary: Approx. $3.92 million

NL Waiver Order (at end of play Sunday): Phillies, Marlins, Rockies, Brewers, Reds, Braves, Padres, Diamondbacks, Nationals, Mets, Giants, Dodgers, Cubs, Pirates, Cardinals

The Diamondbacks view themselves (wrongly) as fringe contenders, but their history with Upton would certainly prevent them putting in a claim, even if the current front office isn’t the one that had him and traded him. The Nationals are an interesting case, freefalling, in turmoil, desperate for a boost … but their offensive deficiencies run much deeper than missing one bat at this point. Maybe Upton would provide enough of a surge to awaken Ian Desmond and Wilson Ramos and all the other underachieving hitters, but that’s a pretty hazy sort of speculation, and anyway, it wouldn’t fix the Nats’ starting pitching, which has been woeful lately.

If Mike Rizzo thinks the Mets will grab Upton if he doesn’t, maybe that’s reason enough for the Nationals to put in a claim, but I don’t think New York would do that, and I don’t think Rizzo thinks they would, either. So let’s talk about what happens if Upton slides past both NL East contenders.

The Giants are absolutely as far up the wire as Upton might go. Their recent success has given them a war chest they only half-heartedly open most of the time; there’s plenty of money sitting there. They would put in a claim in the blink of an eye, and then it would come down to whether San Francisco could sufficiently entice the Padres with a prospect or two, or whether A.J. Preller wants his chance to draft aggressively and rebuild the system he ravaged for nothing last winter.

It’s an interesting question, but a deal is unlikely. The Giants certainly have a prospect or two (or three or four; it doesn’t take a world-beating farm system to provide more value than a late first round draft pick) who could make the Padres pounce, but then they would have to watch that player bloom for a division rival whose resources are already on the rise, and who showed they were serious (if not exactly to be taken seriously, yet) with their wild offseason just a few months ago. In the 40ish games that would be left by the time any deal was transacted, could Upton provide enough value to change the Giants’ fortunes? It’s not impossible (Upton is really, really good, perhaps underrated at this stage of his career), but it’s certainly not a given. Without a certain, concrete benefit, can Bobby Evans justify the possibility that he’ll strengthen a divisional opponent for years to come? Maybe, but maybe not. And at the other end, Preller might reasonably think that the Giants winning a fourth World Series in six years (or anything close to that) would be bad for him in the long run, too.

It’s a bad break for the Padres that the Cubs have hit this August hot streak and raced past the Giants. Chicago could have been a much more comfortable landing spot for Upton, at both ends, especially before Kyle Schwarber cemented himself as a part of the Cubs’ outfield. Plus, there are few teams who would have been better able to offer up something just over comp-pick value without missing it. As it stands, though, it looks like Upton is stuck in San Diego. He’s certain not to be happy about that, and the Padres really shouldn’t be happy about it, either.

Jeff Samardzija

2015 Stats: 163 2/3 IP, 4.78 ERA, 4.01 FIP, 3.74 DRA, 2.35 DRA WARP
Remaining Salary: Approx. $2.65 million

AL Waiver Order (at end of play Sunday): Athletics, Red Sox, Indians, Mariners, White Sox, Tigers, Rays, Twins, Rangers, Orioles, Angels, Astros, Blue Jays, Yankees, Royals

Sometimes the way to look at these things is according to windows. Who is looking at this season and thinking they might have the best chance to win that they’ll have for several years to come? This season, in the American League, the answers to that question have to be the Orioles, the Angels, and the Yankees.

Each of those are very intriguing potential landing spots for Samardzija, but each also presents a complicated case. Baltimore would get the first crack at Samardzija if he hit the wire on Monday, but they might not have the right piece (or pieces) to get a deal done with the Sox. The two sides would have to find the right middle ground, between the few top-end Orioles prospects who would constitute far too much of a return for Samardzija, and the huge collection of stuff that wouldn’t compel the White Sox to act. Even if they found the right name or names, though, the O’s might run into trouble purely in terms of adding that money to their payroll for the final six or seven weeks. It shouldn’t be so, but with Peter Angelos, sometimes it is. The Orioles are at the end of their window, and need to capitalize. They have a crucial dearth of starting pitching depth. It seems like a perfect moment for them to make a big move, but it’s not clear whether they see it that way.

Pretty much ditto for the Angels. They have a window that’s closing fast. They have a glaring need for starters. Unfortunately, they also have a muddled and inefficient management structure, a pointlessly penurious owner, and a very weak farm system. Mike Trout deserves to play in the playoffs again, and the world deserves to watch him do so, but that might not be a good enough argument to move Rick Hahn to give away Samardzija. It’s not clear that the Angels are armed for an acquisition of Samardzija that is anything more than a freebie.

The Yankees probably won’t get a shot at Samardzija. On the other hand, if they have a five-loss week or something and he hits the wire next Monday, they’ll have a much better chance of doing so. If that happens, things get interesting. Samardzija’s salary isn’t going to slow down the Yankees. New York also has a farm system capable of coughing up the right kind of prospect without being crippled. It wouldn’t surprise me to learn that the White Sox are waiting to waive Samardzija, in the hope that they can get him as far as Brian Cashman’s spot on the wire. If it works, Samardzija could move.

What if MLB were more like the NBA?
Many things about the salary-capped, labyrinthine rule set governing NBA roster moves provide individual players with power over the processes by which they change teams. That’s profoundly untrue in MLB. The qualifying offer, though, might be one rule that starts to allow players to claim some agency. Consider: Upton and Samardzija both have a lot to gain by being traded. It’s probably worth more than $10 million over the life of a prospective deal, especially to Samardzija, to get out from under the QO. There’s no mechanism by which either player can really force a trade, of course, other than to be untenably disruptive until they’re dealt, a gambit that would probably hamstring their free-agent value as much as the QO itself.

Maybe under the next collective bargaining agreement, then, we should expect to see more paths to agency in this process for individuals, something beyond the long-standing 10-and-five rights and the no-trade clauses some teams won’t give out. In the meantime, perhaps it’s worth wondering how much a team can gain by doing a player a good turn at a time like this and dealing him. That would be a difficult benefit to quantify, but maybe it’s real. If either Upton or Samardzija does get traded this month, it will be at least trace evidence of that kind of goodwill, because a traditional trade for either is going to be hard to get done.

Thank you for reading

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I'm wondering if the Rangers wouldn't be willing to take Samardzija if he fell into their laps. True, there is no particular reason to think this year is a better opportunity than next year, but, even so, they have thrust themselves into the race and could use the pitching help. I don't know that they would offer much, but blocking him from going to Baltimore or the Angels would be reason enough I would think.
I'm not sure if there was an explanation, but if Baltimore, or any other team claims Samardzjia and can't work a deal, that's it for him being traded right? Any team ranked higher that the Orioles would never have a chance at him this month after that right?
I think you have the strategy wrong. The Nats will absolutely claim Upton, since if the D-Backs let him go, they will happily stick him in LF. Obviously, that won't happen, but they would be the only team that could negotiate any deal with them, so they could make an offer and if the D-Backs say no, they can shrug their shoulders and move on.
The same is true of the Orioles, even more so. No way they let a team above them get a shot.