The Trade Deadline arrives on Friday at 4 p.m. ET, and one of the things that makes this time of year so exciting is its unpredictable nature.

Sure, many of the deals that go down will be ones with some connection to rumors that have been percolating over the previous weeks. Yet there are also always those moves that come out of left field, so to speak.

So while there is no shortage of realistic trade rumors out there, it doesn't hurt to have some fun and go out on a limb, too. To that end, got together five writers and had each cook up a trade proposal that some might call a little crazy. These are the trades that almost certainly won't happen -- but perhaps should.


Motion for the Judge

Braves get: OF Aaron Judge
Yankees get: OF Drew Waters (MLB’s No. 25 prospect), LHP Kyle Muller (Braves’ No. 5 prospect), OF Michael Harris (Braves’ No. 9 prospect)

Why it should happen: The Yankees have sleep-walked their way through a strange and ultimately unsatisfying season in which they are still in contention but showing no real signs of being a threat to win the AL East. They haven’t done enough to display they are worthy of a big acquisition.

So how about a big shakeup?

Judge is a free agent after 2022, and capitalizing on his enormous trade value while bringing in controllable pieces with high upside might actually make sense. The 22-year-old Waters, the 2019 MVP in the Double-A Southern League, is a switch-hitter who is better from the left-hand side (yes, Yankees fans, there is such a thing as batting from the left-hand side), has the skills to play anywhere in the outfield and is on the cusp of the bigs. The 23-year-old Muller has bounced back and forth between the Majors and Triple-A this season and is a long-term rotation piece. The 20-year-old Harris is much farther away but has a really intriguing speed and power skillset.

That’s a lot for the Braves to give up, but … you get Aaron Judge. Ronald Acuña Jr.'s ACL injury was a huge blow to the Braves' NL East chances, which had already been affected by the Marcell Ozuna suspension. But the division is still very winnable, and Judge’s arrival would bandage that gaping wound and keep Atlanta’s World Series hopes alive. Though the newly acquired Joc Pederson is a pending free agent, Judge is still around to pair with a hopefully healthy Acuña (and a hopefully re-signed Freddie Freeman) to give Atlanta a truly monster lineup in 2022.

Why it won’t: The Yankees’ play might not justify a splashy add, but they’re not likely to punt, either. And while Braves GM Alex Anthopoulos isn’t afraid to think big, robbing the top end of the farm system to this extreme is probably a step too far for a 2021 team that just hasn’t lived up to expectations.


A big NL Central swap

Brewers get: OF Bryan Reynolds, RHP Richard Rodríguez
Pirates get: INF Brice Turang (MLB's No. 74 prospect), LHP Aaron Ashby (Brewers' No. 7 prospect), OF Tristen Lutz (Brewers' No. 12 prospect)

Why it should happen: The Brewers rank 10th in the National League in center field OPS thanks to underwhelming seasons from Jackie Bradley Jr. and Lorenzo Cain, each of whom is signed through 2022. Reynolds would be an upgrade for the Brewers, who have a pitching staff capable of a deep postseason run but would benefit from a boost to the lineup. The 2021 All-Star entered Monday slashing .312/.394/.528, and he is not set to reach free agency until after the '25 season.

Turang is expendable given the presence of Willy Adames and Kolten Wong (not to mention Keston Hiura), giving Milwaukee a prime trade chip to deal. Ashby and Lutz would also give the Pirates two players close to being ready for the Majors, while Rodríguez would make a solid Milwaukee bullpen even stronger for the stretch run.

Why it won’t: For Pittsburgh, dealing Reynolds within the NL Central and having to see him in a Brewers uniform 19 times a year for the next four years would be tough. The Pirates are unlikely to deal Reynolds at all given his club control, but for a roster in need of so many upgrades, he’s their best asset. Like all GMs, Ben Cherington likely believes his team can contend in the near future, making Reynolds one of the centerpieces of the rebuild.