The 5 biggest Trade Deadline prospect deals of past decade

With the Trade Deadline quickly approaching on Monday, and rumors swirling around teams looking to make a deep run into October, we thought we would take a look back at the biggest Trade Deadline prospect deals of the past 10 years.

Here's a look at the number of Top 100 prospects that have been dealt at the Trade Deadline each year over the past decade:
2016: 8
2017: 9
2018: 2
2019: 5
2020: 0
2021: 4
2022: 7
2023: 4
2024: 2
2025: 3

On the MLB Pipeline Podcast, Jim Callis and Jonathan Mayo, with host Jason Ratliff, identify the Top 5 biggest trades of the past decade in terms of prospects involved, and with enough time having passed already, the experts weigh in on who won or who lost or if it was a draw -- in some cases, did both sides win or lose?

5. (2021) Nats send Max Scherzer and Trea Turner to Dodgers for a package headlined by two Top 50 prospects: Keibert Ruiz (No. 41) and Josiah Gray (No. 42).

Mayo: Neither Gray nor Ruiz have, I think, lived up to the expectations of where we had them ranked. Ruiz is fine. He's a solid catcher. But, I think if we're grading this trade now, you have to give the Dodgers the win, probably.

Callis: I'm gonna call it a draw. Well, I mean the Dodgers were in "Win World Series or bust" mode. They didn't win the World Series with those guys. Scherzer was there for 11 starts. They held on to Turner, but not long term. I don't think they got what they wanted out of it. This did not put them over the top. And you know, not that Gray and Ruiz became All-Stars, but Gray actually had a couple of nice seasons for the Nationals before he got hurt. And Ruiz, as you point out, he's kind of on the bubble between a regular catcher and a backup catcher. He's been OK, but I bet if you look at -- and I have not done the calculation -- WAR accrued by the teams, the players they received, I think the Nationals might have gotten a little bit more out of it than the Dodgers. So I'm gonna say it's a draw.

4. (2017) A's send Sonny Gray to the Yankees for three Top 100 guys: Jorge Mateo (No. 47), James Kaprielian (No. 58), Dustin Fowler (No. 77).

Callis: I don't think either team enjoyed this trade in retrospect. I mean, Sonny Gray has pretty openly talked about how much he hated playing in New York while he was there. He was there for the end of 2017 and the entire 2018 season. And I think it even came up again this year when he signed with the Red Sox, how much he hated playing in New York and Brian Cashman fired back at him. And then at the same time, none of the players that the A's received: Mateo, Kaprielian or Fowler ever did a whole lot. Kaprielian couldn't stay healthy. He had some moments. You know, Fowler, Mateo, had some flashes. Mateo's had the longest career, but you know, has had essentially one season in the Major Leagues as a regular, and that was with the Orioles, which was a couple teams after he was with the A's. And he's more of a backup utility type. So, I think that was one that at the time there was probably a lot of excitement. The Yankees are like, 'Yeah, we're getting an ace caliber guy.' A’s are like, 'Yes, we're getting three Top 100 prospects' and it didn't work out the way either one of them wanted. So I will again pronounce that a draw. Nobody's happy.

Mayo: I will say the Yankees made it to the ALCS. Sonny Gray pitched very well in the League Championship Series. So, you can make the argument that they get a slight edge just because they did get some value there. He was a big league starter for them for a year-plus and then they were a step away from the World Series and he contributed. [They] won his one start in the ALCS. I'm not saying it's an overwhelming ‘W’ for the Yankees. I'm just saying that might give them a slight edge.

3. (2016) Yankees send Aroldis Chapman to the Cubs in deal headlined by Gleyber Torres (No. 24).

Mayo: This was an interesting one because it's rare that you see a closer go for that high level of a prospect, although it did happen last year in the Mason Miller deal (between the Padres and the A’s) and Leo De Vries. And that was even more rare because De Vries was already in the top five at the time.
I remember thinking at the time that this (Chapman) trade worked for both teams. I feel like this could be a draw just because they both got what they wanted out of it. You know, Torres has gone on to be a big leaguer for a long time, Aroldis Chapman seems to be indestructible, you know.

Callis: This is a win-win. The Cubs won the World Series, which they would not have without Aroldis Chapman. So, they would make this trade a thousand times. And Gleyber Torres soon after that was the best prospect in baseball, and has had a long career. I mean the funny thing is Chapman went back and re-signed with the Yankees in free agency that offseason. So they basically only lost him for two months and they got the best prospect in baseball and they got Adam Warren back and Billy McKinney. So, I think that's one that did exactly what both teams wanted it to.

2. (2017) White Sox send José Quintana to the Cubs for Eloy Jiménez (No. 8) and Dylan Cease (No. 63).

Callis: This trade did not necessarily work out like the Cubs hoped. Quintana never won a playoff game for the Cubs. So, he didn't help them win another World Series. You know, he was with them through the pandemic. But, Eloy Jiménez was the big get in this trade at the time, and he kind of underachieved and he showed flashes but never really, you know, lived up to his billing as one of the very best prospects in baseball. But, it was actually Dylan Cease who turned out to be the real keeper in this trade and who's still going strong. He didn't make his full-season debut till three years after he was drafted because of the Tommy John surgery, but he wound up being the best of them all. He is having another good year this year too. So, I would pronounce that one a win for the White Sox.

1. (2022) Nats send Juan Soto to the Padres for a package headlined by CJ Abrams and MacKenzie Gore (former Top 10 overall prospects who had just graduated from prospect status), Robert Hassell III (No. 21), James Wood (No. 88), Jarlin Susana (Padres No. 14) and Luke Voit.

Mayo: In terms of just the sheer numbers, it's got to be at the top of the list, and this is a really interesting trade because Soto wasn't there for that long in San Diego. I think A.J. Preller does enjoy making huge blockbuster trades and letting guys go. So, Soto was on the move in December of 2023 in another large trade. So, this is a tough one because Soto was a very, very good player for the Padres, but they didn't reach the promised land, then he was gone again. So, I think for the amount of players that were traded, even though the Nationals are still trying to kind of build back, given what James Wood has turned into and Abrams and Gore have established themselves. Even though Hassell was a big name who hasn't panned out and has moved on. I think I give the Nationals the edge in this trade.

Callis: I think it's a clear win. Just to get three building blocks that you controlled for as long as they controlled them. I mean, I know they traded Gore this season, and it's funny because at the time I wrote that I thought even though the Padres gave up a lot, I think you win if you get the best player in the trade. And Juan Soto was 23 at the time, which is why they were able to command so much for him. But, I think the Nationals won this trade.
Also, I mean, I don't know that we'll ever see that much young talent in one trade again because I just don't think you're gonna see a 23-year-old, a player that young and that good, be traded. It just doesn't happen.