If the Yankees are going to reach the postseason again in 2021, general manager Brian Cashman likely needs to ace the Trade Deadline.

It’s been an up-and-down season in the Bronx, but the team is maintaining a win-now philosophy, and reinforcements are necessary to shake up a problematic roster.

We asked five MLB.com writers each to come up with a realistic trade proposal that could put the Bronx Bombers back on the path to success this season. Here are those proposals.

New York Story

Yankees get: SS Trevor Story, RHP Jon Gray
Rockies get: SS Oswald Peraza (Yankees' No. 4 prospect), RHP Albert Abreu (No. 18)

Why it could work: Luke Voit has been unable to stay healthy for most of the season, leaving a void at first base. There’s an easy solution that would make the Yankees’ infield better on multiple fronts: get a shortstop. Adding Story would enable Gleyber Torres to return to second base, while DJ LeMahieu would shift to first base. The Yankees are believed to be interested in signing one of the big-name free-agent shortstops this winter, so getting a two-month look at Story in pinstripes could work to their benefit. Oh, and they get a starting pitcher (Gray) in the deal, too!

For the Rockies, Peraza is a toolsy 21-year-old shortstop who could eventually replace Story in a year or two. The Yankees’ No. 4 prospect (and No. 96 on MLB Pipeline’s overall Top 100 list), Peraza would be expendable if New York plans to ink a free-agent shortstop to a long-term deal, though the club has three other shortstops in its Top 15 prospects. Abreu (the Yankees’ No. 18 prospect) is a hard-throwing righty who may still wind up working as a reliever, but he would give Colorado another young arm in its arsenal.

Who says no: Nobody. The market for Story is limited and the Yankees need to make some short-term moves to get back into contention. Make it happen!

-- Mark Feinsand

Yanks shake things up with J-Ram blockbuster

Yankees get: 3B José Ramírez, OF Bradley Zimmer
Indians get: SS Gleyber Torres, RHP Luis Gil (Yankees No. 5 prospect), OF Kevin Alcantara (No. 12)

Why it could work: Yes, the Yankees need outfielders more than infielders right now, but this trade is as much about 2022 and ’23 as it is about this season. New York’s roster is fundamentally flawed, with too many plodding right-handed hitters and little flexibility. It would hurt to give up on Torres, who is still just 24 years old and produced 62 homers with an .849 OPS over his first two seasons, but the Yanks need to do something bold to salvage their current core’s title hopes.

Ramírez, a switch-hitter and well-rounded star who finished among the top three in the AL MVP Award voting in 2017, ’18 and ’20, would be the spark the franchise needs. The Yanks already have a third baseman in Gio Urshela, but they shouldn’t let that stop them from acquiring a player of Ramírez’s caliber. Besides, with Luke Voit hurt again, the Yankees are going to need DJ LeMahieu to handle first base, leaving an opening at second that Ramírez can fill. This trade also helps New York address its center-field issue. Zimmer doesn’t have much power, but he’s a speedy player who can handle center, bats from the left side and has reached base at a .368 clip over the past two seasons.

In recent years, the Indians have been able to trade key players from their Major League roster for younger and less expensive assets without going through a full rebuild, and this deal would be in a similar vein. Ramírez can be retained for two more seasons via an $11 million club option in 2022 and a $13 million club option in ’23, but he can test free agency after that. Torres is four years younger and controllable through 2024. The other two players Cleveland would get haven’t reached the Majors yet, although Gil is projected to get there by next season.

Who says no: MLB Network insider Ken Rosenthal reported this week that Cleveland will need to be “overwhelmed” to trade Ramírez, and it’s unclear if this deal rises to that level. That said, the Yankees are more likely than the Indians to pass on this one, if only because it would necessitate additional moves, leaving an immediate opening at shortstop and creating a future logjam at third base between Ramírez and Urshela that would need to be addressed in the offseason.

-- Thomas Harrigan

Bombers bring Bucs All-Star to Bronx

Yankees get: OF Bryan Reynolds
Pirates get: RHP Luis Medina (Yankees' No. 7 prospect), RHP Alexander Vizcaino (No. 9)

Why it could work: No one player would fix what ails the Yankees, but they desperately need bodies in the outfield. Bryan Reynolds would be a legitimate boost. He ranks in the 94th percentile in outs above average, for one. He runs well, which few Yankees do. And that’s before you look at his profile as a hitter. He has 17 home runs, which would be the second-most on the Yankees. He’s among the league leaders in expected batting average, slugging percentage and weighted on-base average, speaking to the overall quality of his contact. He’s also been about the same guy since his debut in 2019, which is hard to say about a 26-year-old. If the Yankees need anything, it’s quality contact and a consistent approach. And maybe, if at all possible, fewer ground balls in the middle of the order. (Reynolds’ ground-ball rate is lower than that of Judge, Urshela, LeMahieu and Torres, in case that’s important.)

The Yankees farm system isn’t exactly loaded, but they can probably spare a few right-handers -- the flame-throwing Medina looks like a future big league starter, and Vizcaino’s fate will largely depend on his ability to develop a consistent third pitch. The Pirates have a pretty strong track record in developing young pitchers -- the Yankees themselves can attest to that. Plus, these clubs have spent the better part of the last decade passing players back and forth, even after the transfer to new management in Pittsburgh. That can’t hurt, even if they’ve mostly been dealing in catchers to this point.

Who says no: The Pirates. According to reports, Reynolds is the guy this club wants to build around. And why wouldn’t they? He’s 26 years old, still pre-arbitration and immensely talented. If this is Bryan Reynolds before he’s even hit his prime -- and his consistency would suggest it is -- Pittsburgh has no business moving him, and the front office seems to agree.

-- Shanthi Sepe-Chepuru

A Marte Par-tay in New York

Yankees get: OF Starling Marte
Marlins get: RHP Alexander Vizcaino (Yankees' No. 9 prospect), RHP Albert Abreu (No. 18)

Why it could work: The Yankees desperately need 1) left-handed bats, 2) outfielders and, especially, 3) a center fielder. Although he’s a righty, Marte would fill the biggest hole as a solid defender in center with power and speed -- a dynamic the Yankees lack. The 32-year-old is having another strong season with career highs in OPS+ (128) and walk rate (11.8%) to go with 19 steals. That said, he’s due to hit the open market, so his cost of acquisition shouldn’t be exorbitant (unlike, say, the other Marte: Ketel of the D-backs, who is under club control potentially through 2024). From the Marlins’ perspective, they would add to their stable a pair of hard-throwing righties in Vizcaino (a 24-year-old at High-A with a plus heater and changeup) and Abreu (a 25-year-old with big league bullpen experience). Bonus? This would be another deal between Yanks GM Brian Cashman and his former player-turned-Marlins CEO Derek Jeter.

Who says no: The Marlins. While Miami appears interested in extending Marte, those efforts have yet to come to fruition and there’s enough of a trade market for him -- including possibly the Astros and Phillies, among others -- to drive up the prospect price. With the Yankees on the fringes of the playoff picture, they may not be willing to surrender the type of high-caliber youngster who could be required to acquire Marte.

-- Jason Catania

Whit a fit in pinstripes

Yankees get: OF/2B Whit Merrifield
Royals get: OF Estevan Florial (Yankees' No. 10 prospect), 2B Ezequiel Duran (No. 15)

Why it could work: Merrifield is a DJ LeMahieu type whom the Yankees could use in multiple roles. The easiest fit is to play him in center field (or in the corner), considering the Yankees' big need in the outfield. But they could also play him at second base and put LeMahieu at first, which would make sense since Luke Voit is hurt. Merrifield is about contact and speed on offense, making him a different type of hitter than some of the bigger slugger types in the Bronx Bombers lineup. On the Royals' side, Florial could play in the Majors with them right away. And Kansas City doesn't have a second baseman among its Top 30 prospects, so add in Duran.

Who says no: Maybe the Royals. Merrifield is 32, but trading him doesn't really help the Royals from a contract perspective (he's making $6.75 million this year and $2.75 million in 2022, with a club option for 2023). The two-time All-Star also means a lot to the Royals.

-- David Adler