At this time of year, we all become baseball general managers in our minds. We undertake the fun exercise of crafting theoretical trades that could shake things up ahead of the stretch run as teams look to bolster their rosters in hopes of making a deep postseason run.

Sometimes those trades that we think should happen actually do materialize. And then there are our proposals that don’t become a reality even though we think there’s every reason for the deal to be struck.

• The latest MLB Trade Deadline rumors

With Tuesday’s 6 p.m. ET Trade Deadline fast approaching, and in the spirit of this annual rite, we asked five MLB.com writers to weigh in with trades they think should definitely happen, but for one reason or another, won’t.

*All stats are entering play Friday

The Pirates add power to get Skenes and McCutchen into the playoffs

Pirates get: 1B Vladimir Guerrero Jr. and C Danny Jansen
Blue Jays get: 2B Termarr Johnson (Pirates’ No. 2 prospect, No. 74 overall), LHP Anthony Solometo (Pirates’ No. 3 prospect, No. 75 overall) and LHP Hunter Barco (Pirates’ No. 12 prospect)

Why it should happen: The Pirates, who are just 2 1/2 games out of a Wild Card spot after eight consecutive losing seasons, aren’t quite in “all-out-go-for-it” mode just yet — but that doesn’t mean it needs to be “wait ‘til next year” yet again, either. Imagine what it might look like in October if they could manage to sneak into a postseason spot, then roll out a starter group of Paul Skenes, Mitch Keller, Luis L. Ortiz (two earned runs in four starts since moving to the rotation) and/or Jared Jones, who should return from injury in August. It’s the kind of stuff wild and unexpected postseason runs are made of.

But it will remain a fantasy, both for this year and the ones to come, if the Pirates can’t find some bats. While Bryan Reynolds has been strong and Andrew McCutchen good enough, this has been a bottom-five offense in 2024, and even recent resurgences from Oneil Cruz (who has posted an .813 OPS after a slow April) and Rowdy Tellez (.931 OPS since June 15) have only managed to turn the July Pirates into a middle-of-the-pack unit.

It is, to be clear, not a good enough lineup — especially from the right side — and while you’d like to think they have several years to figure that out around their talented young pitching, it should be clear by now that counting on young, healthy pitching to remain young and/or healthy for long is risky at best. It’s not now or never, but now isn’t that far away from now, either.

That, then, positions them perfectly for a wild move that would help both this year and next, by acquiring Guerrero Jr. from the flailing Jays. For a time, Vlad felt so overrated that he is now underrated, in that he’s been fantastic for months (.325 BA and .928 OPS since May 1), yet never seems to get the credit for it given that he hasn’t matched his wonderful 2021.

Imagine Guerrero’s bat filling out a top-four along with McCutchen, Reynolds and Cruz. Imagine getting the lefty Tellez into a 1B/DH/PH rotation, rather than absolutely counting on him to continue a run out of step with the rest of his career. Imagine Jansen, who despite a slow season has been for several years a righty power bat, stepping in to replace the declining 35-year-old Yasmani Grandal (46 OPS+).

Imagine, mostly, the idea of Skenes starting a playoff game as a rookie at PNC Park with franchise legend McCutchen leading it off. It can be real.

Why it won’t: Though the Blue Jays seem like clear sellers, it’s still more likely than not that they’ll retain Guerrero, who still can’t be a free agent until after 2025, and if they do decide to trade him, it might also set forth some dominoes in the Toronto front office, adding only more chaos to the situation. So, he might not even be available, but even if he is, there’s also the matter of the likely-more-than-twenty-million-dollars he’ll make in his final year of arbitration next year. It might be that the outfield is a larger Pittsburgh problem to solve, anyway.

— Mike Petriello

Reds surprise with blockbuster that helps in 2024 and beyond

Reds get: LHP Garrett Crochet, OF Luis Robert Jr.
White Sox get: 3B Noelvi Marte, RHP Rhett Lowder (Reds’ No. 1 prospect, No. 20 overall), 3B Cam Collier (Reds’ No. 3 prospect, No. 83 overall), RHP Luke Holman (No. 71 overall pick in 2024 MLB Draft) and SS/3B Ricardo Cabrera (Reds’ No. 8 prospect)

Why it should happen: The thought of adding the 25-year-old Crochet to a rotation that already includes emerging youngsters Hunter Greene (24), Nick Lodolo (26) and Andrew Abbott (25) is incredibly enticing from the Reds’ perspective. And while Cincinnati is fairly well off in the infield, especially with Matt McLain on his way back from left shoulder surgery, the team’s outfield could use some star power. Reds outfielders have posted a .691 OPS in 2024, the 16th-highest mark in MLB.

At 50-53, the Reds are trending toward selling at the Trade Deadline, but this trade is just as much about the future as it is 2024. Crochet is controllable through 2026, while Robert can be retained through ’27 if both of his club options ($20 million each in 2026 and 2027) are picked up.

Adding Crochet and Robert would set up the Reds to be a viable contender in a winnable division over the next couple of years. The Reds also aren’t fully out of it in 2024, so this trade would keep them in the mix for an NL Wild Card spot, even if they still decided to sell off some of their veterans.

In exchange for Crochet and Robert, the White Sox get back what is essentially three MLB Pipeline Top 100 prospects (Marte has graduated from the list but was the No. 21-ranked player coming into 2024) plus two other young pieces. It may seem like a steep package, but that’s likely what it would take to get Chicago to move Crochet and Robert in the same trade.

Why it won’t: Although Crochet and Robert both have multiple years of team control remaining, this still seems like a “win-now” move, and it’s unclear if the Reds are ready to take such an aggressive swing for the fences while they are still trying to establish themselves after a rebuild.

The White Sox, meanwhile, will likely want to trade Crochet and Robert separately to maximize the return.

— Thomas Harrigan

Yanks fill a gaping hole at third and address their problem hitting lefties

Yankees get: 3B Ryan McMahon and C Elias Díaz
Rockies get: RHP Chase Hampton (Yankees’ No. 3 prospect, No. 81 overall), RHP Will Warren (Yankees’ No. 7 prospect), 2B Jorbit Vivas ( Yankees’ No. 15 prospect) and LHP Caleb Ferguson

Why it should happen: The Yankees need offensive production outside the dynamic duo of Aaron Judge and Juan Soto. And the Bronx Bombers need that production from third base, in particular — they’ve gotten a .228/.290/.308 slash line from the hot corner so far this year. Enter the 29-year-old McMahon, who is having a career year at the plate to match his well-established defensive prowess. He hit his 15th home run of the season on Wednesday and has an .802 OPS.

The left-handed-hitting McMahon also hits lefties well, something the Yankees have had trouble with in 2024, slashing .228/.326/.370 this season against southpaws. McMahon has an .844 OPS against left-handers this season and could provide some much-needed punch in New York’s lineup behind Judge and Soto, whom opponents have been able to pitch around with relative impunity.

The same goes for Díaz, who could be a solid addition behind the plate for New York, especially with Jose Trevino still sidelined with a left quad strain. Díaz is one of the better hitting catchers in the NL. He’s also hitting .282 in 78 at-bats against lefties this season.

For the Rockies, this is a chance to do something they like to do in Colorado — stockpile pitching. The trouble at the moment is that most of their better pitching prospects are in the low Minors, not coming up to help in the big leagues any time soon. Dealing McMahon, who has three years remaining on his contract, could net a fairly substantial return. Acquiring a pair of top pitching prospects from the Yankees, as well as a veteran left-handed reliever in Ferguson, could be a golden opportunity.

Why it won’t: The Rockies tend to hold onto homegrown players. Colorado had the opportunity to trade shortstop Trevor Story and right-hander Jon Gray — each on an expiring contract at the time — prior to the Trade Deadline in 2021, and dealt neither (though Story’s elbow injury certainly may have had something to do with it in his case). And last year, veteran Charlie Blackmon, who posted an .852 OPS over 171 second-half plate appearances, apparently wasn’t shopped as a potential DH for a contending team.

The Rockies signed McMahon to a six-year extension in 2022, and he’s owed $44 million over the final three years of the contract. That’s an attractive contract for a club looking to acquire him, but McMahon and inquiring teams have reportedly been told he isn’t going anywhere. Díaz may certainly be moved, but it appears McMahon will be manning the hot corner for the Rockies the rest of this season and beyond.

— Manny Randhawa

Braves add good bat and defensive versatility

Braves get: OF/IF Ian Happ
Cubs get: P AJ Smith-Shawver (Braves’ No. 1 prospect, No. 65 overall), C Drake Baldwin (Braves’ No. 10 prospect)

Why it should happen: The Braves are in desperate need of offense, especially in the outfield. Since April 27, they’ve hit .227 as a team with a .665 OPS. Both marks rank last in the NL and 28th in MLB during that stretch, in which they’ve gone 36-41. Much of the lack of outfield production can be blamed on the season-ending injury to 2023 NL MVP Ronald Acuña Jr. and the loss of center fielder Michael Harris II for what will end up being about two months. But with Atlanta still aiming for a postseason berth and a deep run into October, and with Adam Duvall (.184 average, .560 OPS) and Eddie Rosario (.182 average, .552 OPS) really struggling in the corner spots, a productive bat at the Deadline is a necessity.

Happ, meanwhile, is having a strong year for the Cubs and would give the Braves’ lineup a big boost. His 16 homers and 121 OPS+ would both rank second among the Atlanta starting nine. Plus, his ability to play outfield and infield spots would give the Braves options should they want to rest guys down the stretch. The switch-hitting Happ would also be under team control for two more seasons.

On the Cubs’ side, Smith-Shawver, Atlanta’s No. 1 prospect who’s looked good in spots in his limited MLB work, could give them a young and exciting rotation arm for 2025 and beyond. The Braves are obviously high on Smith-Shawver but believe he needs a little more seasoning to tackle command issues. But his high-90s fastball, strong slider and solid changeup could make for an electric combo.

Baldwin, the Braves’ No. 10 prospect, has the potential to be a good MLB catcher with pop. He has good plate discipline and has developed into a better hitter as he’s ascended through the Minors. In 82 games this season between Double-A and Triple-A, Baldwin has 10 homers and a .745 OPS. But since his promotion to Triple-A, he’s hit .284 with an .898 OPS in 30 games.

Why it won’t: Depending on who’s talking, it would be an overpay or an underpay. The Braves seem unlikely to part with Smith-Shawver, given his upside and some rotation issues after this season (Max Fried’s free agency, Charlie Morton’s potential retirement). But the bigger issue might be what Atlanta would do with Happ after this season. With Acuña, Harris and Jarred Kelenic all signed for the long haul in the outfield, Happ could be the odd man out, even with his defensive versatility. Second base and third base, Happ’s other positions — though he hasn’t played either since 2021 — are spoken for next season with Ozzie Albies and Austin Riley, respectively. Also, given that it’s a seller’s market, the Cubs might want more certainty in the return for the productive Happ.

— Jason Foster

Dodgers get the answers they need for October … from their rivals

Dodgers get: LHP Blake Snell, 3B Matt Chapman
Giants get: LF Miguel Vargas, RHP River Ryan (Dodgers’ No. 4 prospect), SS Trey Sweeney (Dodgers’ No. 21 prospect), SS/2B Noah Miller (Dodgers’ No. 26 prospect)

Why it should happen: The Dodgers are in World-Series-or-bust mode (as always). They’re looking for a top-flight starting pitcher, and the left side of their infield is decimated by injuries. The Dodgers aren’t looking for stopgaps, though. With their lofty goals, they need proven, “postseason difference-maker” players to get them through October, not just to October.

The Giants have the solutions the Dodgers need. Snell’s looking more like his Cy Young self with every start, and he’s a lot more experienced than someone like Garrett Crochet, who hasn’t even started until this year, let alone started for a postseason run. Chapman is a rock at third base who could lock it down even if Max Muncy returns down the stretch. The Dodgers would have the flexibility to play Muncy at second if they want his bat in the lineup, like they’ve done in previous seasons, or they can keep Gavin Lux there if they want a better defender.

The Giants hoped Snell and Chapman would jump-start the team into playoff contention this year when they snapped them up on short-term bargains. But they’ve fallen to five games under .500 at 50-55. They’re not catching the Dodgers in the NL West, and they’re not in great shape in the Wild Card race either, with a whole mass of teams between them and the last spot. So why not take this opportunity to set up for a 2025 playoff push by adding young Major League-ready players? San Francisco might want to make that push with Snell and Chapman, but they would have to hope a reigning Cy Young winner and Gold Glove third baseman exercise their player options to stay in San Francisco.

The Dodgers can afford to take a chance on Snell and Chapman to get two impact players for the 2024 postseason, and they have a wealth of those young, big league-ready players that would help the Giants. The 24-year-old Vargas is already in the Majors and was MLB’s No. 37 prospect a year ago; he could take over in the corner outfield with veteran Michael Conforto set to become a free agent. The 25-year-old Ryan just got called up and shined in his Major League debut; he’d help replace Snell. Sweeney is 24 and has 13 homers and 15 steals at Triple-A; he could jump in on the left side of the infield going forward. And the 21-year-old Miller is an upside trade chip to round out the deal, who’s farther away from the big leagues but could (ideally) become a Brandon Crawford-type player for San Francisco.

Why it won’t: These two teams just don’t trade with each other. The Dodgers and Giants have made a grand total of three trades since they moved to California. The most recent one was in 2007, and it wasn’t near the blockbuster this one would be — the Giants sent Mark Sweeney to the Dodgers for a player to be named later.

This trade would be one of the biggest splashes of the Deadline, and to make it happen, two longstanding division rivals would have to come together and swap some big pieces. Are the Giants really willing to give up two star players during the same season they brought them in, and do it when they’re still “only” 5 1/2 games out of the playoffs? Do the Dodgers, who seem to turn so many prospects into rising stars, give up a whole haul of them for players they passed over as free agents in an offseason where they made the biggest free-agency splash of all time? Maybe not, but it would be cool to see.

— David Adler