The Diamondbacks negotiated a trade with the Mariners last week, one that would have netted a strong package of young talent. But when the two teams finally agreed to the deal, the trade’s centerpiece vetoed it. Which means the D-backs are right back in the same position they’ve been in for much of the past several months: trying like mad to trade Justin Upton.

There are several perfectly defensible reasons to deal him. The Diamondbacks have the National League’s biggest outfield logjam, with Jason Kubel, Cody Ross, Gerardo Parra, and top prospect Adam Eaton all joining Upton in being major league–ready outfielders seeking regular playing time. We’ll ignore for the moment that said logjam is largely self-imposed, that after flipping Chris Young and his eight-figure salary to Oakland (thus giving the A’s the AL’s deepest outfield) Arizona figured it’d make sense to give Ross a three-year deal to fill a hole that didn’t exist. The D-backs also have bigger holes to fill elsewhere, with adequate but uninspiring incumbent Chris Johnson this season’s projected starting third baseman; shortstop isn’t ideal, either, with banjo-hitting veteran Cliff Pennington the expected Opening Day starter and all-glove/little-bat prospect Didi Gregorius waiting in the wings, but surely GM Kevin Towers isn’t so trigger-fingered that he’s going to make a third trade for a shortstop in three months, right? Finally there’s Upton himself, a maddeningly inconsistent player if you look at his year-to-year numbers since taking over the everyday right-field job five years ago:

There are mitigating factors here. A shoulder injury hurt his production in 2010, and an early-season thumb injury was so debilitating at the start of the year that Upton was hitting just .221/.317/.328 as late as mid-May. Still, there might be something more at play. Industry buzz claims Diamondbacks GM Kevin Towers isn’t a big Upton fan; no one knows exactly why, though some rival executives have speculated that D-backs brass don’t see Upton as a “winning player,” whatever that means.

His sometimes unpredictable numbers aside, Upton is still a 25-year-old masher with ample upside and three years and $38 million left on his contract, making him one of the most desirable trade commodities in the game. So when Arizona’s obsession with trading Upton advanced beyond the rumor stage, we probably shouldn’t have been surprised to see the Mariners reportedly offering a package that would have contained one of Seattle’s top three pitching prospects (Taijuan Walker, James Paxton, or Danny Hultzen), top shortstop prospect Nick Franklin, plus a pair of live-armed relievers in Charlie Furbush and Stephen Pryor. With that trade rejected, you have to wonder: Have the Diamondbacks lost their leverage?

On one hand, the rest of baseball now has to figure that Arizona really wants Upton gone, lest nothing happen and the young star return to the desert for a fiesta of awkwardness. On the other, teams make it known all the time that players are on the trading block. As long as those players have actual value and are attractive to multiple teams, the seller will always retain a healthy amount of leverage.

To see if the Diamondbacks should be expected to land a handsome return — at least one that rivals what Seattle supposedly offered — let’s dig up some precedents. We’re not looking for standard-issue fire sales: No Padres shopping Fred McGriff in ’93, no Marlins every-15-years Apocalypse Clearance, no John Wetteland for Fernando Seguignol and a lifetime of self-loathing. Instead, we’re seeking situations more similar to Upton’s, in which a quality player signed to a reasonable-or-better contract is being shopped hard, for reasons ranging from “we don’t like that guy’s attitude,” to “collect underpants.”

Acknowledging the risks of smallish sample size and selection bias, let’s see if we can at least find some anecdotal evidence of some kind of trend that could tell us what the D-backs might get back if they do find a taker for Upton (thanks to Rany Jazayerli and others for some of these suggestions):

June 15, 1977: Mets trade Tom Seaver to Reds for Doug Flynn, Steve Henderson, Dan Norman, and Pat Zachry

Seaver’s skills had slipped a little from peak levels in his 20s, but he was still coming off a season in which he tossed 271 innings, led the league in strikeouts, and posted an ERA that was 26 percent better than league average. A dispute over money was in play, as Seaver lobbied for compensation that at least rivaled the best pitchers in the league, while notoriously ornery Mets GM M. Donald Grant dug in his heels. Still, the two sides put aside their differences and coexisted reasonably well for a while. Until, that is, New York Daily News shit disturber Dick Young started lobbing Molotov cocktails on the situation. A sample of Young’s regard for Seaver:

Tom Tewwific [is] a pouting, griping, morale-breaking clubhouse lawyer poisoning the team.

By the summer of ’77, Seaver had had enough, informing the Mets in no uncertain terms he wanted out immediately. For a pitcher of Seaver’s caliber, you’d think that any potential for a lack of leverage would be overpowered by rampant demand from other teams. Turns out, not so much. The Mets got a grab bag of mostly mediocre talent from Cincinnati, with none of the players coming back fitting the top-prospect mold you’d expect to find in today’s youth-and-service-time-obsessed game.

March 26, 1992: Brewers trade Gary Sheffield and Geoff Kellogg to Padres for Ricky Bones, Matt Mieske, and Jose Valentin

Sheff wasn’t anywhere near the destroyer he’d become later in his career, his best year a .294/.350/.421 effort through the first three-plus seasons of his career. Of course the Brewers had also called him way too soon at age 19. A combination of injuries, Sheffield lacking an obvious defensive position, and Milwaukee’s periodic refusal to play him also held back his progress. Still, the raw talent was there, and the Brewers might’ve held onto the no. 6 overall pick longer if not for a gigantic rift that emerged between player and team. Sheffield accused the Brewers of racism multiple times, particularly when they pushed him off shortstop to third base in favor of mediocre, pigment-challenged infielder Bill Spiers. Things got so bad that Sheffield eventually started chucking throws into the stands, admitting later he was deliberately making errors so management would give up and ship him to another team.

He’d run into problems with multiple other employers, with eight stops over his 22-year career. But the Padres might’ve made out best of all in terms of value, probably less because of Milwaukee’s lack of leverage than because of other teams’ fears that the guy might be a little crazy. Turns out he was … and any team would have been lucky to have him anyway.

July 14, 2010: Braves trade Yunel Escobar and Jo-Jo Reyes to the Jays for Tim Collins, Alex Gonzalez, and Tyler Pastornicky

I didn’t get it. There were rumors that Escobar didn’t take instruction well at best and was a pain in the ass at worst. All I saw from the outside was a 27-year-old asset going through a brief rough patch who’d shown he could be solidly above average both offensively and with the glove. We’ve gained some insight since then. Escobar chafed his next employer, this time through a much more public gaffe.

Of all the players on this list, Escobar’s the one whose trade value was most clearly damaged by off-field factors, especially in that first trade. If the D-backs end up being forced to sell Upton at such a steep discount, something’s gone terribly wrong.

July 27, 2011: Cardinals trade Colby Rasmus, Trever Miller, Brian Tallet, and P.J. Walters to the Jays for Octavio Dotel, Edwin Jackson, Marc Rzepczynski, and Corey Patterson

There are Tony La Russa’s guys, and then there are the guys Tony La Russa wishes could be demoted to the Cardinals’ rookie-ball affiliate in Sao Tome and Principe. Rasmus fell into the latter camp. The two clashed frequently during Rasmus’s time in St. Louis; and then there was the public buzz surrounding Rasmus and his dad fighting with La Russa over how the young outfielder should be handled, while privately … we probably don’t know the whole story. A decade earlier, La Russa had grown disenchanted with another talented, mid-20s hitter just starting to hit his stride, in that case over perceived problems with effort and conditioning. Turns out the problems over Fernando Tatis’s effort and conditioning were warranted, and Tatis’s career started evaporating on the first day he took the field for the Expos. The book is still very much wide open on the 26-year-old Rasmus, though through 189 games with the Jays he’s hitting a cool .213/.273/.384, triggering cries among some nervous Nellies for Anthony Gose, Lloyd Moseby, Mats Sundin, or anyone else.

But we’re here to discuss the return. And despite the cries and wails of many in the analytical community, it’s tough to argue with the results. The Cardinals went from having one of the worst bullpens in all of baseball to one of the best by the time they hoisted their second World Series trophy in six seasons, partly due to the maturation of Jason Motte and other incumbents, but also via addition by subtraction, jettisoning the likes of Miller, Tallet, and Walters, and adding an excellent righty-lefty setup combo in Dotel and Rzepczynski. Jackson made the rotation deeper, Jon Jay took the everyday center-field job and ran with it, and thanks to one of the most memorable postseasons runs of all time, La Russa got the best retirement gift a manager could ever have. It’s not standard practice to flip a mid-20s center fielder stuffed with tools for a walk-year number-three starter, some bullpen arms, and a pinch-runner. But the pieces sure as hell fit.

July 30, 2011: Rockies trade Ubaldo Jimenez to the Indians for Alex White, Drew Pomeranz, Matt McBride, and Joseph Gardner

When news first broke that this trade had gone down, it was nothing less than a shocker — a pitcher who’d been one of the league’s best a year earlier signed to an incredibly attractive contract. Only later would we find out that the Rockies were fielding offers from multiple teams for their ace right-hander. If you dug deep, you could see a few signs of erosion. His fastball was down a couple ticks, though we shouldn’t necessarily hang our hats on four months of data. His home-run rate was up, though you could have argued that as predictable regression after a ludicrous 2010 season in which he allowed 10 in 33 starts. Really, from a distance, you could have excused pullbacks across the board given the Cy Young–caliber effort he’d put up a year earlier. Turns out there was a lot more going on. Jimenez’s fastball velocity dropped again in 2012, as did his swinging strike rate. His command, never perfect, left him completely last season, his walk rate climbing to a career high of 4.8 per nine innings.

So did the Rockies get good value for the pitcher few publicly (but many privately) knew was being shopped? Tough to say. The two supposed gems of the deal, White and Pomeranz, rode a season-long roller coaster. If all they’d had to do was ride the shuttle from Colorado Springs 70 miles north to Denver, that’d be one thing. If all they’d had to do was deal with mile-high elevation and the least-friendly environment for pitchers, that’d be another. But White and Pomeranz, like other Rockies starters, also dealt with changing roles throughout the year, as the staff flipped from a traditional five-man to four and back. If in some parallel universe Jimenez were a Padre, and San Diego had bagged that much loot in a trade, we might very well be evaluating the deal in a different light. Then again, if Jimenez is reduced to a low-90s-throwing walk machine who can’t get through six innings, then any return could be a big plus.

OTHERS

• Randy Johnson was two months away from free agency when Seattle traded him to Houston at the 1998 deadline, but there Upton-like circumstances were involved, too. The Mariners announced they wouldn’t give him a contract extension because of concerns over his back. He’d struggled with a sub-.500 record and a 4.33 ERA, seeing spikes in his walk and home-run rates, but also suffering from some bad luck due to an elevated batting average on balls in play. Johnson’s suitors were plentiful anyway, and a return of Freddy Garcia, Carlos Guillen, and John Halama was a strong one for two months of the Big Unit, both at the time and in the years that followed.

• Manny Ramirez was a better comp, a free-agent-to-be but also someone who was unwanted by his team despite remaining highly productive at the time of the deal. Boston had to give up Manny as well as young right-hander (and once highly regarded prospect) Craig Hansen as well as lefty-swinging corner man Brandon Moss for Jason Bay. This was before Bay’s career went up in smoke, and the Sox got 45 homers in 200 games for their trouble, albeit with an LCS loss in 2008 and a first-round sweep at the hands of the Angels the next.

• Trevor Bauer was another case of a team becoming frustrated with a player perceived to be tough to coach and rein in. As with Upton, Bauer’s name had been floated repeatedly for months, a shocker for a first-round pick whose big league career was just getting started. In Bauer’s case, the Diamondbacks actually pulled the trigger, landing Gregorius but also setting up the Indians as potentially huge winners in the deal.