Regrading 5 of the most lopsided deals from the 2023 MLB trade deadline

The 2024 MLB trade deadline is just nine days away as of this writing. As fun as it is to look ahead at what's to come, it's also fun to look back in hindsight and make fun of teams who made deals that look just dreadful one year later.

To be fair, hindsight is 20/20. Deals that look like fleeces now didn't all look that way at the time they were completed. Still, what's done is done, and it's appropriate to now look back at the deals that didn't quite age well.

These five trades in particular stick out as the most lopsided deals executed at the 2023 MLB trade deadline.

5) The Jeimer Candelario trade did not age as well as the Cubs had hoped

The Chicago Cubs were in the thick of the postseason race last season and acquired one of the best bats available, Jeimer Candelario, to try and get them over the hump.

At first, the deal looked like it was going to age wonderfully. Candelario had eight hits in his first nine at-bats with Chicago, with three of those hits resulting in extra bases. The Cubs scored 36 runs in their first two games with Candelario. Unfortunately, he'd struggle most of the rest of the way, and even missed a couple of weeks due to injury.

After those first two games, he slashed .188/.279/.391 with six home runs in 39 games played. The Cubs narrowly missed out on the postseason. Perhaps if Candelario swung a better bat, Chicago would've squeaked into the postseason over a team like the Diamondbacks who happened to win the NL Pennant.

What makes the deal look worse is the emergence of DJ Herz as a potential future building block for the Washington Nationals. Herz was promoted earlier this season and has a 5.17 ERA in 10 starts, but has shown flashes of brilliance in the process.

The right-hander already has a pair of double-digit strikeout performances including his third MLB start in which he fanned 13 Marlins. Sure, it's the Marlins, but that's still impressive. Overall, Herz has 41 strikeouts in 31.1 innings of work compared to just nine walks. There's more work to be done, but he has serious potential.

Kevin Made hasn't done much to make Chicago regret including him in the deal, but Herz alone is too much to give for two good games of Candelario who departed for a division rival in the offseason.

Cubs trade regrade: C-
Nationals trade regrade: B

4) Acquiring Bailey Falter proved to be a big win for the Pirates

This deal didn't generate many if any headlines at the 2023 trade deadline and still doesn't look like anything groundbreaking, but the Pittsburgh Pirates did really well here in retrospect.

Bailey Falter was an important piece for the 2022 Philadelphia Phillies who won the NL Pennant, but took a major step back in 2023. Because of that, Philadelphia traded him to Pittsburgh in exchange for Rodolfo Castro, an infielder who'd give them depth, particularly against left-handed pitching. Or so they thought.

Castro had just three hits in 30 at-bats down the stretch for the Phillies last season and has been limited to just five minor league games all of this season. In other words, he has contributed nothing since being acquired by the Phillies.

On the flip side, Bailey Falter struggled last season for the Pirates but has a 4.08 ERA in 17 starts this season for Pittsburgh. He has been rock solid at the back end of their rotation. Do the Phillies miss him? No, not really, but they should've gotten a whole lot more than Rodolfo Castro for him in retrospect. Again, hindsight is 20/20.

Phillies trade regrade: D-
Pirates trade regrade: B+

3) The Angels made several bad trades at the 2023 trade deadline

Some trades are judged harshly in retrospect that actually made some sense at the time. The Los Angeles Angels refusing to trade Shohei Ohtani when they faced an uphill battle to make the postseason made little sense and doubling down to buy only made it worse. They traded some of the only good prospects that they had in a brutal farm system only to immediately collapse and go nowhere near sniffing the postseason.

This trade with the Chicago White Sox is a prime example of just how poorly their trade deadline went.

The Angels traded their two best prospects at the time, Edgar Quero and Ky Bush in exchange for two rental pitchers, Lucas Giolito and Reynaldo Lopez. They were both gone one month later when the Angels waived several veterans in a last-ditch effort to dip back under the luxury tax when they were all but eliminated from postseason contention.

Lopez pitched well for the Angels, but he was used exclusively in relief. He has now blossomed as a starting pitcher in Atlanta. Giolito was having a decent year with the White Sox but had an ERA approaching 7.00 in his six starts for the Halos.

They got one month of both of those pitchers and gave the White Sox two prospects, one of which is the No. 72 prospect according to MLB Pipeline. Bush has seen his stock take a bit of a dip, but Quero alone makes this a fleece on Chicago's end considering what the Angels got.

Neither of these players has debuted for the White Sox yet, but once they do, the pain will be even worse for Angels fans.

Angels regrade: D-
White Sox regrade: A-

2) The Paul Sewald trade made little sense at the time and looks worse now

Despite being in a postseason race, the Seattle Mariners inexplicably traded their closer. Yes, offense was more of a need for them, and Andres Munoz is more than capable as a replacement, but did they really have to trade Paul Sewald to the Arizona Diamondbacks to get bats who aren't even all that great?

Josh Rojas is the best player that Seattle acquired and he played pretty well for them down the stretch last season, but he has just a .675 OPS this season. Dominic Canzone's OPS is at .684 this season. Ryan Bliss, a prospect at the time, didn't do much with the 31 games of MLB action he received earlier this season.

In return for this underwhelming package, the Mariners coughed up Paul Sewald, a reliever who closed games for the NL Pennant-winning Diamondbacks last season and has had another strong year in 2024.

The Mariners' biggest issue was its offense when they made this trade. Their biggest issue continues to be its offense one year later. In fact, it's worse now than it was then. The new additions haven't done much at all to make things better.

A team in contention should never trade its closer, especially when the return is as underwhelming as this one is shaping up to be.

Mariners trade regrade: D
Diamondbacks trade regrade: A

1) The Royals stole a future ace at the 2023 trade deadline

I get it. The Texas Rangers won the World Series last season, so they shouldn't really regret anything they did. Still, even the biggest Rangers fans have to admit that this deadline swap has aged horrifically, and that's after Texas was mostly praised for making the deal.

Ragans, out of nowhere, has blossomed into a legitimate ace. He was dominant down the stretch for the Kansas City Royals last season and has a 3.16 ERA in 20 starts and 116.2 innings of work this season. He was an All-Star, will almost certainly receive some Cy Young votes if he can stay healthy, and doesn't even hit arbitration until after next season.

Ragans is one of the most valuable pitchers in the American League right now and is playing a huge role in Kansas City's emergence. Meanwhile, the Rangers simply didn't get much in retrospect.

Aroldis Chapman was an upgrade for a bullpen that sorely needed it. He had his ups and downs as he always does, but he was mostly solid in the postseason for a Rangers team that, again, won the World Series.

A trade like this is hard to grade super fairly because of Texas' win, but the reality of the situation is that Texas traded a future ace with tons of club control for half a season of an inconsistent set-up man. They won the World Series so it's worthwhile and saves it from being an F, but that doesn't mean this isn't a bad trade that they made along the way.

Rangers trade regrade: D+
Royals trade regrade: A+