A Conversation With the ‘Angel and Devil’ on the Shoulders of Five GMs

MLB’s trade deadline is fast approaching. For teams in the postseason hunt, is it time to buy in or sell high on stars?

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We are less than a week away from the trade deadline, but we’ve hardly seen any activity on the transaction wire (the Mets’ acquisition of Daniel Vogelbach is notable but hardly the stuff of fever dreams). That’s partially because the amateur draft was later than usual this year, not occurring until last week, which commanded attention from front office executives that would otherwise be spent on preparing for trades. The expanded playoff field may also be contributing to the standstill, giving hope to teams who may otherwise have started looking toward next year and beyond—at the beginning of play Wednesday, 18 of 30 teams were within 3.5 games of a division lead or wild-card spot. With only 12 playoff teams, that number would’ve been 15.

Enough with the excuses, though. It’s high time for everyone to commit to a strategy and give us some action. So let’s sort through the decisions these fringe contenders face about whether to buy or sell. For the second straight year, I’ve laid out the arguments in a conversational format. On one side, there’s the optimistic buyer. On the other is the cold, calculating seller. I like to think about it as the trope with an angel and devil on either shoulder of the protagonist. It’s impossible to tell now whether the buyer or seller is the angel who will lead to salvation. But let’s do our best to distinguish the best way forward.

San Francisco’s division-winning dominance from last year hasn’t carried over into this season, mainly because its bullpen and defense have been atrocious. Should the Giants try to upgrade those two areas or deal a few players with the goal of contending again in 2023?

AP Photo/Ross D. Franklin

San Francisco Giants

Seller: We’ve officially hit a new low. Our loss to the Diamondbacks on Tuesday night put us below .500 for the first time this season and extended our six-game losing streak. We’re closer to the last-place Rockies in the NL West standings than we are the second-place Padres. As for the Dodgers? Don’t ask. We can forget about defending our division title.

Buyer: We’re still only 2.5 games out of a wild-card spot. And our 51–46 Pythagorean record, which is based off of run differential, suggests we are a playoff team. Plus, the Braves just won the World Series last year when they were under .500 on Aug. 4!

Seller: Yeah, but the Braves were still just a few games back of the Phillies and Mets at that point. We’re 16.5 games behind the Dodgers—I told you not to ask—and heading in the wrong direction. Plus, after everything went right for us last year, it feels like the opposite has been true in 2022. Breakouts from last year such as LaMonte Wade Jr., Steven Duggar, Tyler Rogers, Zack Littell and Dominic Leone have badly regressed.

Buyer: We knew that was bound to happen with some of those guys. And we’ve managed to dig up some other diamonds in the rough like Luis González, Jakob Junis and John Brebbia.

Seller: A bunch of veterans we hope we could depend on (Evan Longoria, Brandon Crawford and Tommy La Stella) are currently on the injured list—and the latter two haven’t been particularly valuable when healthy. Even All-Star starting outfielder Joc Pederson has been one of the league’s worst hitters in July (his 20 wRC+ ranks 196th out of 198 players with at least 60 PAs this month) while continuing his abysmal work in the field. And he’s not alone there. Just about every all-encompassing defensive metric grades us as one of the league’s worst fielding teams.

Buyer: Our defense could definitely use some work. But our rotation has been the best in baseball according to FanGraphs’ version of WAR, which values how good we’ve been at limiting home runs. And we’re tied for fifth in runs scored. The real problem has been our bullpen, which has been a bottom-five unit by ERA (4.38) and not much better by the metrics. That’s the easiest unit to upgrade in July.

Seller: Much of the bullpen’s issues trace back to the poor glovework, which is much tougher to turn around midseason—especially when it’s been an issue all around the diamond. Despite our solid offense, center field is the only position where we’ve accumulated a positive mark in wins above average. That’s a direct result of shoddy defense just about everywhere. We may have underestimated the importance of that aspect of the game when constructing this team.

Verdict: SELL, except if you’re getting Juan Soto. Carlos Rodón is almost assuredly opting out of his contract in the offseason and would immediately become the top pitcher on the block if San Francisco makes him available. Pederson should be much more sought after than he was last summer despite his recent swoon. Perhaps he’d be a good luck charm if nothing else, as he’s seeking to become the only player in MLB history to win three consecutive World Series titles with three different teams.

Pablo López is the most likely trade candidate among Miami’s talented group of young starting pitchers. With the Marlins deal from their surplus of quality arms to improve their lineup for the next few years?

AP Photo/Lynne Sladky

Miami Marlins

Seller: Why would we buy this year? We only have a 3.1% chance to make the postseason, per FanGraphs, and have gone just 20–31 against teams currently holding a playoff spot, the worst mark of any NL team within five games of a postseason berth.

Buyer: You’re right! We probably won’t qualify for the playoffs this year.

Seller: So … you give up? Just like that? You think we should sell?

Buyer: Nope. Who do you want us to sell? We couldn’t get teams to take the big salaries of Avisaíl García or Jorge Soler—who’ve both been extremely disappointing in the first year of their newly signed contracts—with the way they’ve been hitting. It’s probably the same story with Jesús Aguilar, with his career-low marks in walk rate and exit velocity—and he’s the only person on our roster who’s certain to enter free agency in the winter.

Seller: This is true. We’re seriously outgunned on offense. Our 95 wRC+ ranks 21st in MLB. So what do you suggest we do?

Buyer: There’s not much use in shopping for rentals. But there’s plenty of room for improvement up and down the lineup, which gives us flexibility to acquire hitters with a lot of variety in how they’re viewed on the market, as long as they have multiple years of team control remaining. Miguel Andújar and Dominic Smith present buy-low opportunities with multiple years of arbitration remaining, while All-Star Ian Happ could slot in anywhere in our uninspiring outfield and excite our fan base. That’s just to name a few.

Seller: Alright, fine. Just don’t forget we’re still a couple of years away from our contention window.

Verdict: BUY, but for the future. Use some pitching prospects the front office isn’t internally as high on as other teams are to get hitters who could help for multiple years.

Woof, things have been a brutal recent stretch for Boston. Over the past decade franchise has been known for quickly rebuilding its roster after one or two rough seasons. Is that the right course for the 2022 Red Sox?

AP Photo/Michael Dwyer

Boston Red Sox

Seller: Someone from our team told ESPN’s Jeff Passan that we should wait and see how we did against the Blue Jays, Guardians and Brewers coming out of the All-Star break before determining what do it. If that’s a significant factor in our decision making, the choice should be clear. We were swept by Toronto in a three-game set and split our first two games against Cleveland, and were outscored 49–16 in those five games.

Buyer: We shouldn’t let a handful of games dictate our long-term outlook.

Seller: Yeah, you’re right. But the big picture isn’t much prettier. We’re now in last place in the AL East—yes, even behind the *shudders* Orioles—and are sitting at 49–49. We have the worst record against winning teams (31–40) of any AL contender. Since July 4, we have the worst record (4–14) and run differential (-73) in the majors.

Buyer: Our schedule has been brutal over that stretch. We’ve only played the Yankees, Rays, Blue Jays and Guardians in that time. They’re all looking like playoff contenders.

Seller: Yeah, and we haven’t looked like we’re in the same stratosphere as them.

Buyer: We were in the ALCS just last season!

Seller: This isn’t the same team. We let Kyle Schwarber, Eduardo Rodriguez, Adam Ottavino and Martín Pérez walk in free agency, then dealt Hunter Renfroe for Jackie Bradley Jr. in a trade that hasn’t worked out. Chris Sale is out indefinitely after his freak broken finger accident. Trevor Story has been a below-average hitter by wRC+ (and is also injured at the moment). James Paxton never threw a pitch for us before he was declared out for the year. We basically had one fantastic month in June (20–6) and three others that exposed our weaknesses and lack of depth.

Buyer: Our pitching has been our clear weakness. If we get a good starter to pair with Sale once he’s back, we could turn things around.

Seller: Luis Castillo and Frankie Montas are the only obvious difference-making starters on the market. Even if we get one of them, our pitching staff is more than just a starter away from being World Series-worthy. The overall staff ranks 23rd with a 4.31 ERA, and the bullpen actually ranks even lower than the rotation when compared to other teams. Even our offense is a roughly average unit. We just don’t have enough here to merit a push.

Verdict: SELL. The good news is that Boston boasts plenty of soon-to-be free agents who would be attractive rentals for potential trade partners. Nathan Eovaldi and J.D. Martinez could fetch significant returns. Perhaps even Xander Bogaerts would waive his no-trade protection to go to a contender and upend the position player market. Others include starters Michael Wacha and Rich Hill, catcher Christian Vázquez, utilityman Kiké Hernández and reliever Matt Strahm.

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The Guardians have a throwback roster that favors contact, baserunning and defense over home runs, but that doesn’t mean they shouldn’t add some thump, so long as they prioritize controllable players over rentals.

AP Photo/Nam Y. Huh

Cleveland Guardians

Buyer: We’re 2.5 games back in both the AL Central and the wild-card race! It would look pretty pathetic if we threw in the towel now, barring a catastrophic conclusion to our road trip through Boston and Tampa Bay. What’s there to debate here?

Seller: Look, all I’m saying is that Shane Bieber’s free agency isn’t that far off (after the 2024 season). He’s only going to get more expensive for our tight-fisted owners, and we have a tendency to recoup what we can for our elite starters before they reach the open market. What do you say?

Buyer: Not again! Not yet! Given the shallow state of our rotation, it is absolutely necessary we keep Bieber for this season if we’re to make a playoff run. Plus, his strikeout rate has taken a massive hit over the past couple of seasons, from 41.1% during his shutdown Cy Young campaign in 2020, to a reduced yet still impressive 33.1% last season to a downright pedestrian 24.3% this year. Trading him now wouldn’t make a lot of sense because we wouldn’t get as strong of a return.

Seller: Fine. What do you want, then?

Buyer: Well, we could use a catcher who can hit a lick, another starter, another bat … and who couldn’t use another reliever?

Seller: Slow your roll.

Buyer: I’m not saying we should acquire all of those pieces. But putting a dent in our long-term shopping list would be nice. A’s catcher Sean Murphy, who’s set to enter arbitration for the first time this winter, would fit our organization’s M.O. of valuing catchers with top-tier defensive chops—while providing a sizable upgrade on offense over Austin Hedges, whose 48 wRC+ ranks 28th of the 30 catchers with the most plate appearances. Really, any bat with team control beyond this season would suffice. Franmil Reyes, our 6’5”, 265-pound DH with two 30-home run seasons under his belt, has hit fewer homers than Andrés Giménez, who entered this season with eight career dingers across parts of two seasons. That’s left a big hole in our lineup.

Verdict: BUY. None of the needs are acute given the organizational timeline, but they are aplenty.

The Orioles are the talk of the league right now after their surprising surge has trusted them into the playoff race. Are they contenders or pretenders?

AP Photo/Julio Cortez

Baltimore Orioles

Buyer: After beating Tampa Bay on Tuesday, we have a winning record almost 100 games into the season. I think it’s fair to say neither of us expected this.

Seller: Yeah, I thought this would be one of my easiest sell jobs of the year. Had visions of sending Trey Mancini out of Baltimore by now, his deep connection to the city notwithstanding. Maybe even Austin Hays or Cedric Mullins. Now even I’ll admit I’ll be lucky to get Jorge López out of here.

Buyer: You sure would be. Not only are we the toast of Baltimore at the moment, but we’re also the toast of the league. Everyone wants to see us do well. No one wants to see the mighty O’s dismantle their first competitive team to emerge from one of the biggest teardowns in MLB history.

Seller: Even you must admit this team is still not built to win this year. The No. 1 starter is Jordan Lyles, who’s on his sixth team in as many years. The offense’s 94 wRC+ ranks 22nd in the majors, the worst placement of any realistic playoff contender. And FanGraphs still gives us just a 3.1% chance of making the playoffs.

Buyer: Perhaps not. In a world where we were truly going for it this year, the obvious advice would be to shop for rotation help. But that’s easier said than done in this starter-starved market, and I realize it doesn’t make sense to gamble the farm for a quick fix after all these years. That being said, there are some minor upgrades we could pursue. Believe it or not, the only offensive position where we account for negative wins above average is second base, where Rougned Odor was meant to boost his value before a summer selloff. Instead, his production has been below replacement level. So why not bring in Cincinnati’s Donovan Solano to displace him? Solano has virtually even splits for his career and could cheaply improve the most glaring weakness in our lineup. If he’d cost too much prospect capital, perhaps Whit Merrifield could be acquired as at least a platoon split and perhaps more if he starts to resemble his former self.

Seller: I’m not sure Baltimore is the destination to convince Merrifield to get vaccinated in the name of suiting up for a contender. And we still have six more games to play in Toronto.

Buyer: That would be unfortunate. But honestly, Merrifield would cost next to nothing, and trading for someone like him would be more about showing the fans that we’re ready to move into the next phase of our rebuild and keep them coming out to Camden Yards.

Seller: Ugh, I hate symbolic gestures. If you insist on something like that, why don’t we sell high on a reliever or two while we’re at it? Baseball’s top insiders have been suggesting some teams could be looking to both buy and sell, and we look like a good candidate for that approach. We’ve somehow cobbled together MLB’s best bullpen, at least in terms of wins above average, win probability added and fWAR. Relievers are popular around this time of the season, but they have the most high-variance propositions from year to year. We really have no clue if López, Keegan Akin, Cionel Pérez or Félix Bautista will be this good when we’re a bonafide playoff threat. So let’s strike while the iron is hot.

Verdict: The rare measured, double-pronged approach of BUY AND SELL seems like a solid one for the O’s.

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