The 10 Things You Need to Know About the MLB Trade Deadline

The MLB non-waiver trade deadline — the busiest transaction period of the regular season and the de facto start of the stretch run — isn’t until July 31, but several contenders have already started loading up for their march to October. We’re just getting started, though, and you’re going to need to be familiar with several people, things, and concepts in order to understand all the trades, both real and rumored, over the next week and a half. Here are 10 that are worthy of special note.

1. Sonny Gray

One consequence of each team using at least five starting pitchers is that just about every club could stand to upgrade its rotation. But with so many teams in the wild-card hunt, particularly in the American League, there are relatively few sellers. Most teams would want to hold onto their top starting pitchers because they’re close enough to talk themselves into making a run, and typically, the teams that are completely out of the race aren’t exactly teeming with top-end starting pitching.

One such team, the White Sox, dealt staff ace José Quintana to the Cubs last week, leaving Gray as the biggest name on the starting pitching market, at least for the moment. A 27-year-old with a top-three Cy Young finish under his belt, Gray has been linked to the Brewers, Yankees, Royals, Astros, Cubs, Braves, and Indians just since Monday. He’s pitched like a no. 1 starter within the past three years, and at his age, and with two more years of team control beyond 2017, he’d make an attractive target for anyone with designs of making the playoffs in the near future.

The question of just how attractive is a little more complicated. Following that third-place Cy Young finish in 2015, Gray made just 22 starts with a 5.69 ERA last year, thanks to a strained trapezius and a strained forearm, and then a strained lat muscle cost him all of April this year. Since returning, Gray’s got a 3.72 ERA with 79 strikeouts in 84.2 innings, which is pretty good, but it’s not exactly ace-level production.

But with so many suitors and few other pitchers with Gray’s track record on the market (at least until someone else falls out of the race), Oakland has to convince only one team that Gray is worth somewhere between what the White Sox got for Quintana (a top-10 global prospect plus three other guys) and what the Phillies got for Cole Hamels in 2015 (three top-50 prospects plus Jerad Eickhoff, Alec Asher, and Matt Harrison).

2. Rental Ace

Gray and Quintana are both under team control for several years, but there’s a proud tradition of playoff-bound teams trading for two months of a top-level starter in the hope that they’re one arm from getting to the playoffs, or even the World Series. More often than not, the rental ace doesn’t make all the difference, but sometimes the heat of the pennant race brings out the best in both pitcher and team, and the rental ace becomes a mythical figure in team folklore.

Some notable examples:

• 1984: Free agent–to-be Rick Sutcliffe moves from Cleveland to the Cubs in June as part of a seven-player trade. Sutcliffe wins 16 of his 20 starts and wins the NL Cy Young, while the Cubs make the playoffs for the first time since 1945. Sutcliffe re-signs with Chicago in the offseason.
• 1992: Toronto trades Jeff Kent to the Mets for half a season of David Cone, which would be a tough pill to swallow if Cone hadn’t helped the Blue Jays win their first World Series.
• 1998: Houston trades Freddy Garcia, Carlos Guillen, and John Halama to Seattle for Randy Johnson, who goes 10–1 with a 1.28 ERA down the stretch and gets two NL Cy Young votes for 11 starts. The Astros finish 102–60, but lose in the first round to San Diego as Johnson goes 0–2 despite allowing just three earned runs in two starts.
• 2008: Milwaukee trades four prospects, including Michael Brantley, to Cleveland for CC Sabathia, who goes 11–2 with a 1.65 ERA, with seven complete games, three of them shutouts, in 17 starts, the last three of them on three days’ rest. Sabathia finishes fifth in Cy Young voting and sixth in MVP voting for half a season’s work. Milwaukee makes its first playoff appearance in 26 years, but loses in the first round to the Phillies.
• 2010: Texas pries Cliff Lee from Seattle in a six-player deal. Lee sets the AL record for K/BB ratio, strikes out 13 in eight scoreless innings in Game 3 of the ALCS, and starts the first World Series game in franchise history.
• 2015: David Price posts a 2.30 ERA in 11 starts for Toronto after coming over from Detroit at the deadline, then starts the Jays’ first playoff game since 1993. The Jays finished short of the World Series, but had some fun along the way.

When the rental ace works out, it generates a citywide frenzy that might be my favorite thing in baseball. There’s something about a team not only getting over the hump, but rewarding its fans by landing a big-name pitcher. If the Rangers fall off in the next week, we could see this happen again, since free agent–to-be Yu Darvish has the capacity to put together a two-month run like the ones listed above.

3. Brad Hand

As a team with no pretentions of contending in the short term, the Padres are probably in a position where a relief pitcher is more valuable to them as a trade chip than in any other capacity, and they’ve got a good one in lefty Brad Hand. He was waived by the Marlins last April, but since arriving in San Diego, Hand has been superb: a 2.92 ERA with a 30.5 percent strikeout rate in an MLB-leading 82 appearances last year, then a 32.1 percent strikeout rate and a 2.25 ERA in 48 innings so far this year. And Hand isn’t just a LOOGY: He’s been tougher on righties than lefties this year, and he’s recorded four or more outs in 33 of his 125 appearances since joining the Padres. Hand will almost certainly move, and whoever picks him up might get a poor man’s Andrew Miller.

4. Buying in Bulk

The Louisiana Purchase wasn’t supposed to involve more than 800,000 square miles’ worth of territory. American envoys Robert Livingston and James Monroe were tasked with buying just the key port city of New Orleans, until French Foreign Minister Talleyrand came back to them and asked how much they’d pay for the whole of Louisiana.

Over the past few weeks, negotiations for bullpen help have taken a similar course as contending teams have started buying bullpens more or less wholesale: Washington picked up both Ryan Madson and Sean Doolittle from Oakland, while the Yankees went to the White Sox hoping to acquire Tommy Kahnle, and came home with Kahnle, David Robertson, and third baseman Todd Frazier.

This approach suits not just the Nationals, who actually needed an entire bullpen, but the modern playoff pitching staff in general. In 2014, the Royals rode a starting rotation of James Shields, Yordano Ventura, and “we’ll figure out the rest later” to Game 7 of the World Series because they could call on five knockout relievers to pitch as many as six innings a night. Just last year, Cleveland sent four prospects, including top-100 guys Clint Frazier and Justus Sheffield, to the Yankees for Miller despite having top-end closer Cody Allen in the fold already. That approach allowed them to survive injuries that decimated their starting rotation and get to within a few outs of winning the World Series.

When everyone needs five good relievers, sometimes it’s just easier to get all your shopping done in one place rather than try to wrangle several trade partners in separate deals.

5. The Mighty Giancarlo Stanton’s Contract

Not every trade involves a contender: Ken Rosenthal of Fox Sports outlined a potential blockbuster trade between the moribund Phillies and the moribund Marlins. Philadelphia’s five years into a rebuild and has the worst record in baseball, with a big league roster that has some interesting young pitchers but produces fewer runs than a truckload of hard-boiled eggs. Miami, meanwhile, is interested in liquidating future financial liabilities in advance of the sale of the franchise.

There is no greater financial liability than TMGS, who’s in Year 3 of the richest contract in the history of North American team sports. Rosenthal’s rumored trade would involve the Phillies taking on TMGS and Christian Yelich, two outstanding outfielders aged 27 and 25, respectively, in exchange for taking on some $339.5 million in outstanding salary over the next decade, in addition to sending a collection of prospects to Miami.

The Phillies, a big-market team with almost no long-term commitments at the moment but a history of spending to the luxury tax in the past, are uniquely suited to take on that kind of contract, though a deal like this would be as unprecedented as the contract that caused it.

6. Ground Control

In the heady days of the Best Breach in Baseball, back in 2014, nearly a year’s worth of Astros internal trade discussions were leaked to the public. Some of the highlights included a “TMGS for Carlos Correa and George Springer” trade, but the Astros were ridiculed for a couple of outrageous trade asks, including either Xander Bogaerts or Jackie Bradley Jr. for Bud Norris, and Lucas Giolito for Lucas Harrell.

The lesson here is twofold. The first is that we all know the guy who calls in to local sports radio asking why the Cubs can’t get Mike Trout for Jeimer Candelario (a good prospect, but not a great one), Jason Heyward (a contract the team wants to get rid of), and “two B-level prospects.” It’s not like teams don’t try to make trades like that, it’s just that opposing GMs are usually too smart to get suckered anymore. The second lesson: Everything is a negotiation. If it seems like a team’s asking for the moon for a player who isn’t that good, it’s because that team’s GM wants to make sure the Bogaerts-for-Norris trade isn’t out there before retreating to a fallback position.

7. Peter Angelos

The Orioles owner is famously hands-on, occasionally undermining GM Dan Duquette by nixing signings after Duquette agreed to terms with free agents. Angelos is usually reluctant to go into rebuilding mode, but according to Rosenthal, he has given Duquette his blessing to shop outfielder Seth Smith and Baltimore’s top relief pitchers.

Baltimore has an abundance of top relievers. Brad Brach has a 172 ERA+ with 224 strikeouts in 198.2 innings since 2015. Mychal Givens has a 211 ERA+ in 48.1 innings this year, while Richard Bleier has a 325 ERA+ in 33.2 innings. The best of the bunch, however, is Zach Britton, who’s just returned from a forearm injury. Britton’s allowed 35 earned runs in 224 innings since the start of the 2014 season. For comparison, San Diego’s Jered Weaver allowed 35 earned runs in 42.1 innings this year.

If you’re looking for top-end relievers in bulk, Baltimore is the place to go.

8. Rafael Devers

The Red Sox have a great rotation, the best closer in the game in Craig Kimbrel, and a solid lineup top-to-bottom, with the exception of third base where, as The Ringer’s Zach Kram wrote, the situation is dire. Last year’s starter, Travis Shaw, was traded to Milwaukee in the offseason, and Pablo Sandoval was just DFA’d after hitting .212/.269/.354 this year. The Red Sox player with the most starts at third this year is 26-year-old Deven Marrero, who’s hitting .211/.255/.324. That’s better than Cleveland got from its catchers last year en route to the World Series, but Boston would probably like to head into October without an automatic out in the lineup.

The Sox were reportedly in on Frazier, who as a free agent–to-be, would’ve been able to plug the hole temporarily without representing much of a future commitment, but now he’s in pinstripes two states south. The Red Sox could pursue another external option — and it wouldn’t take much for them to upgrade — or they could promote from within.

Devers was no. 5 on the Baseball Prospectus midseason top 50, seemingly the only prospect team president Dave Dombrowski didn’t trade for Kimbrel or Chris Sale since he took over. Devers hit .300/.369/.575 at Double-A before he was promoted to Triple-A last week, and at age 20, he’s still got some development left. In a perfect world, Boston would probably like to keep him in the minors through the end of the season.

But in a perfect would, Marrero wouldn’t have a 52 OPS+, and considering the recent tradition of young third basemen being pressed into service in an emergency (Manny Machado in 2012, Bogaerts in 2013), at some point, Devers might be the best of a set of imperfect options. If Dombrowski doesn’t agree, look for Boston to make a move for any third baseman he can get his hands on.

9. David Stearns

Milwaukee’s lost 4.5 games in the standings to the Cubs since the break, but life is still good for baseball’s youngest GM. For the Brewers, being in first place this late in the season is found money — nobody expected Milwaukee to be this good or the Cubs and Cardinals to be this bad.

The sell-off portion of the rebuild ended last year with trades of Jonathan Lucroy and pitchers Will Smith and Jeremy Jeffress, but this season, Stearns has to figure out how heavily he wants to reinforce his current position. The Brewers could use some middle infield help or another starter, and everyone needs another relief pitcher, but if Stearns decides he wants to be a player for the likes of Gray, it could complicate everyone’s deadline plans.

10. The End of the Royals

The Royals are .500, and 1.5 games out of both the division and wild-card lead. They’re poised to lose their top starter, Jason Vargas, to free agency, along with center fielder Lorenzo Cain, third baseman Mike Moustakas, first baseman Eric Hosmer, and shortstop Alcides Escobar. Their best reliever, Mike Minor (which is a clause that requires some unpacking), has a $10 million mutual option for next season, which is a lot of money for a middle reliever. Several other players, most notably starter Danny Duffy, are due raises next year, which would dampen the Royals’ ability to find top-notch replacements in free agency. Meanwhile, the farm system isn’t barren, but it’s not exactly teeming with ready replacements in the upper minors.

No matter what, next year is going to suck, and GM Dayton Moore has two options: He could sell off his free agents–to-be now, figuring his team isn’t that great, and retool, if not for 2018, then for 2019 or 2020. Or he could go all in now and add players at the deadline, chasing the 11.8 percent chance of a playoff spot Baseball Prospectus gives him, since that’s the best shot he’s likely to get for a few years.

It’s a difficult decision made more so by the involvement of the core of the 2014–2015 teams, and depending on how Kansas City’s next week goes, it could become another suitor for Gray, Darvish, or Lance Lynn, or it could flood the market with Vargas, Moustakas, and Cain. I don’t know what Moore’s going to do. Not only that, I don’t know what I’d do if I were Moore.

All stats updated through Thursday night.