Ranking the Big Winners of the 2021 MLB Trade Deadline

| August 6, 2021 7:06 am PDT

The following teams made great moves at the 2021 MLB trade deadline and set themselves up for future success. That future success could come as early as this year or in the next few years, but either way these teams are better off than they were before the trade deadline.

It is always hard to predict how impactful prospects will be down the road, but all great players were once prospects. Nowadays especially, you can see the top tier teams have had great farm systems and are a big reason why they are successful today.

With that being said, let’s look at the MLB trade deadline winners for 2021, ranking the top seven.

7. Chicago White Sox

The White Sox made a couple of trades with their crosstown friends and now have possibly the best bullpen in all of baseball.

The Cubs weren’t doing very well this season, but their strong suit was their bullpen. Craig Kimbrel is back to his dominant form and Ryan Tepera was having a great year as well.

Both went from the North Side to the South Side at the deadline in separate trades, and now the White Sox add to their already top tier bullpen.

Going back to the Cubs were players 2B Nick Madrigal, RHP Codi Heuer, and LHP Bailey Horn. The White Sox didn’t have to give up a bunch of highly rated prospects to have possibly the best bullpen in baseball.

They will be very dangerous when the postseason comes around.

The White Sox also added some depth to their lineup with acquisitions of 2B Cesar Hernandez from the Indians and C Deivy Grullon from the Rays. They sent LHP Konnor Pilkington to Cleveland and cash to Tampa Bay.

6. Toronto Blue Jays

The Blue Jays acquired some talented players at the 2021 MLB trade deadline this season.

Their biggest acquisition comes from Minnesota. Jose Berrios is one of the young starting pitchers in the league who had potential of being traded this year, and Toronto was able to grab him.

Berrios is pitching to a career low ERA of 3.31 in 2021 and doesn’t become a free agent until 2023. The Blue Jays ended up having to trade away their second and fourth best prospects for Berrios.

SS/OF Austin Martin is now second ranked for the Twins, while RHP Simeon Woods Richardson gets bumped up to the third spot.

The Blue Jays also added two bullpen pitchers, LHP Brad Hand from Washington, and RHP Joakim Soria from Arizona. Both become free agents at the end of the year.

The Blue Jays have two of the league’s best young stars. SS Bo Bichette and 1B Vladimir Guerrero Jr. are both a major part of the team’s future.

Guerrero Jr. is an MVP candidate this year and will probably be in the conversation every year he plays.

Toronto’s star talent and win-now mentality are why they wanted to grab Berrios, who has more than half a season left on his contract.

5. Washington Nationals

The Nationals were another team who got a lot of good prospects at the deadline. They had to bite the bullet and trade away their ace, Max Scherzer, who was due to become a free agent at the end of this season.

The same goes for the speedy shortstop, Trea Turner.

Turner and Scherzer are both free agents at the end of this season and the Nationals flipped them for great prospects.

As I mentioned earlier, the Nationals return included the Dodgers first, second, 10th, and 27th ranked prospects.

The Nationals also flipped several other veterans.

  • C Yan Gomes
  • 2B Josh Harrison
  • SP Jon Lester
  • RHP Daniel Hudson
  • OF Kyle Schwarber
  • RP Brad Hand

Gomes, Josh Harrison, and cash were sent to the A’s for prospects C Drew Millas, RHP Seth Shuman, and RHP Richard Guasch. Millas and Guasch rank within the Nationals top 30 prospects at 24th and 30th, respectively.

Lefty Jon Lester was sent to the Cardinals for outfielder Lane Thomas, as well. Thomas was ranked as the Cardinals 14th best prospect in 2020, but only batted .104 in his first 32 games this season. That is still a good return for Lester, who was on a one-year deal.

The Nationals sent RHP Daniel Hudson (who becomes a free agent after this season) to the Padres for RHP Mason Thompson and SS Jordy Barley. Thompson is now the Nationals 16th ranked prospect, while Barley is 28th.

Next, the Nationals shipped OF Kyle Schwarber to Boston. Schwarber was another player who was on a one-year contract and the Nationals traded him for RHP Aldo Ramirez. Ramirez is now the Nationals 11th ranked prospect.

Lastly, the Nationals sent Brad Hand to the Blue Jays for C Riley Adams. Adams is now ranked 13th in the Nationals system.

The Nationals were very busy at the deadline, and they got a great return for most of their players who were becoming free agents at the end of
the season.

They can now build around their young star outfielder, Juan Soto, who is under control until 2025.

4. Miami Marlins

The Marlins were going nowhere this year. They currently sit in last place in the NL East and decided to flip some players on their active roster for some prospects.

They shipped away OF Starling Marte, OF Adam Duvall, Closer/RHP Yimi Garcia, and RHP John Curtiss.

The reason why they are 2021 MLB trade deadline winners in my book is because of the quality prospects they got in return.

For Starling Marte, the A’s sent the Marlins pitcher Jesus Luzardo.

Luzardo was the highest ranked prospect in the A’s system last year and has huge upside. The A’s ended up trading Luzardo in favor of Starling Marte, who becomes a free agent at the end of this year.

This move was very puzzling to me because of how high Luzardo was ranked as a prospect and he was flipped for an outfielder who will only be on the team for half of the 2021 season. Luzardo is 23 years old and doesn’t become a free agent until the 2027 season.

This is a huge steal for the Marlins, especially if Luzardo can reach his ceiling as an MLB player.

The other prospects they got include C Alex Jackson, C Payton Henry, RHP Austin Pruitt, and OF Bryan De La Cruz.

The Marlins capitalized on trading away their players who were not a part of the team’s long-term success and did well at the MLB trade deadline.

3. New York Yankees

The Yankees made some surprising moves at the deadline this season. They sat 8.5 games back of first place with a 44.4% chance of making the playoffs on July 29th.

New York was undeniably one of the most disappointing MLB teams from the first half of the season.

Nonetheless, they were buyers at the deadline. They made their 2021 roster better at the deadline, but if they don’t make the postseason, that could turn them into losers.

The Yankees acquired big lefties Anthony Rizzo and Joey Gallo.

Rizzo becomes a free agent at the conclusion of this season, while Gallo becomes a free agent the following year in 2023.

Rizzo and Gallo fit perfectly in the Yankees lineup with heavy hitting righties, Giancarlo Stanton and Aaron Judge. Their offensive resurgence can be exactly what the Yankees needed to make the postseason in 2021.

Along with Gallo, the Yankees also got LHP Joely Rodriguez and cash. The Yankees had to give up 2B Ezequiel Duran, SS Josh Smith, IF/OF Trevor Hauver, and RHP Glenn Otto.

The new prospects already rank within the Top 30 on the MLB Pipeline. Here is how they are currently ranked.

  • 7. SS Josh Smith
  • 8. 2B Ezequiel Duran
  • 18. IF/OF Trevor Hauer
  • 25. RHP Glenn Otto

They also had to give up their ninth and 12th ranked prospects in RHP Alexander Vizcaino and OF Kevin Alcantara in order to get Rizzo from the Cubs.

The Yankees were able to acquire LHP Andrew Heaney from the Angels and RHP Clay Holmes from the Pirates. They sent RHP Janson Junk and RHP Elvis Peguero to the Angels for Heaney and IF Diego Castillo and IF Hoy Park to the Pirates for Holmes.

These were costly moves for the Yankees, but they are all in on 2021 despite being in third place in the AL East.

2. Los Angeles Dodgers

The Dodgers made huge moves at the deadline with the intention of being the first team to repeat World Series victories since the 1998-2000 Yankees. 

The biggest trade they had was the acquisition of Max Scherzer and Trea Turner from the Nationals.

The price was steep, but this was the biggest single trade throughout the entire deadline.

The cost for the three-time Cy Young winner and talented shortstop was enormous. It cost them their number one and two prospects, and two others.

Here’s the total haul Washington got in the deal.

  • C Keibert Ruiz
  • RHP Josiah Gray
  • RHP Gerardo Carrillo
  • OF Donovan Casey

Ruiz and Gray were the top prospects the Dodgers had, while Carrillo ranks as the Nationals number 10 prospect and Casey ranks as their number 27 prospect.

The Dodgers weren’t done there. They made a deal with the Royals, acquiring LHP Danny Duffy and cash for a Player to be Named Later. Duffy is currently on the 10-day IL with a forearm injury and will make his Dodgers’ debut later this season. Duffy has pitched 61 innings this year to an impressive ERA of 2.51.

The Dodgers also acquired outfielder Billy McKinney from the Mets for prospect outfielder Carlos Rincon and cash. McKinney will be extra outfield depth for the Dodgers as the Mets get a lower ranked prospect in return.

In total, the Dodgers emptied out a lot of their prospects and now only have one within the top 100 on the MLB pipeline.

That said, they got what they needed to repeat in 2021.

They had some issues with their big free agent signing last season, Trevor Bauer. Bauer is currently on the MLB’s Administrative List and could be out for the remainder of the season.

Scherzer and Turner will be immediate impact players for the Dodgers as they prepare for a close race in the NL West with the Giants and Padres. Turner will be playing second base instead of shortstop with the return of Corey Seager from the 60-day IL.

1. Chicago Cubs

Cubs fans are going to hate this, but the Cubs made the right decision at the 2021 MLB trade deadline.

They traded away their beloved players in favor of young prospects. No matter which way you look at it, the Cubs core has underperformed since their World Series victory in 2016.

The following big names got sent packing.

  • Kris Bryant (3B)
  • Anthony Rizzo (1B)
  • Javier Baez (SS)

All three of these guys were due to become free agents at the end of this season and the Cubs sit in fourth place in the NL Central. This team would have had an enormous hill to climb, especially when the first place Brewers have had one of the best records in the MLB in the past couple months or so.

Instead of trying to fight a very tough battle, the Cubs made the move to set themselves up for future success. If the Cubs didn’t trade their superstars, they could have ended up missing the playoffs and losing their core to free agency anyways.

The Cubs had a 1.3% chance to make the playoffs on July 28th, according to Fangraphs.com.

Here is a breakdown of the trades the Cubs made before the trade deadline.

Traded Away Traded For Trade Partner
OF Joc Pederson 1B Bryce Ball Braves
RP Andrew Chafin OF Greg Deichmann
RHP Daniel Palencia
RP Ryan Tepera LHP Bailey Horn White Sox
1B Anthony Rizzo RHP Alexander Vizcaino
OF Kevin Alcantara
OF Jake Marisnick RHP Anderson Espinoza Padres
RP Craig Kimbrel 2B Nick Madrigal
RHP Codi Heuer
White Sox
SS Javier Baez
RHP Trevor Williams
OF Pete Crow-Armstrong Mets
3B/OF Kris Bryant OF Alexander Canario
RHP Caleb Kilian

If there was a representation of “it’s a business,” this is it right here. The Cubs talked about extending their core earlier this season but ultimately none of them agreed to an extension.

The offers the Cubs gave probably weren’t going to change after the season because they opted to trade them away while they still could.

The Cubs prospect outlook is much better with this massive haul. Here is a look at how some of these prospects are ranked in the Cubs’ prospect rankings.

  • 6. OF Pete Crow-Armstrong (from Baez)
  • 7. OF Alexander Canario (from Bryant)
  • 8. RHP Alexander Vizcaino (from Rizzo)
  • 11. OF Kevin Alcantara (from Rizzo)
  • 16. RHP Caleb Kilian (from Bryant)
  • 20. OF Greg Deichmann (from Chafin)

Codi Heuer and Nick Madrigal have already made their major league debuts from the Craig Kimbrel trade, but the rest of the prospects look to be a few years away from the major leagues.

It will be very interesting to see how the return will be from this massive collection of trades in the next decade or so.

In my book, the Chicago North Siders are set up for a brighter future than they were before the trade deadline. It was unfortunate for the Cubs to deal such fan favorites, but they came away as the biggest 2021 MLB trade deadline winners because of it.

Other 2021 MLB Trade Deadline Winners

  • San Francisco Giants
  • Texas Rangers

The above seven teams have set themselves up for future success by making smart moves at the 2021 MLB trade deadline. Even though these two teams below didn’t make the cut, they are worthy of honorable mention.

The Giants traded for one of the biggest names on the market in Kris Bryant. They also added LHP Tony Watson from the Angels. They didn’t have to give up a prospect ranked within their top eight as well.

The Rangers got a great haul of players for Joey Gallo. All four of the players acquired from the Yankees now rank within the team’s top 30 prospects, as mentioned earlier.

Although they did well with their trade with the Yankees, it seems like they didn’t get enough for their trade with the Phillies.

They sent RHP Kyle Gibson, RHP Ian Kennedy, and RHP Hans Crouse. Gibson has 2.86 ERA on the year, while Kennedy has an ERA of 3.41. They were having solid seasons so far, but the questionable part comes with Hans Crouse. Crouse was ranked as the Rangers ninth best prospect, but now he ranks fourth on the Phillies.

The cost for these Rangers players were RHP Spencer Howard, RHP Kevin Gowdy, and RHP Joss Gessner. Howard was a second-round pick in 2017 and was once a highly rated prospect, but Gowdy and Gessner do not rank within the Rangers’ top 30 prospects.

The return for Joey Gallo was amazing, but the trade with the Phillies makes them less of a “winner” at the deadline.

Ultimately, these are the biggest winners at the 2021 MLB trade deadline. Of course, only time will tell just what that translates to when it comes to playoffs and championships.

Anthony Haage

Anthony is a sports writer for GamblingSites.com covering the NFL, NBA, MLB, NHL, and more. He also covers other various topics such as entertainment, general sports betting tips, and more.

His favorite teams are the Chicago Bears, Bulls, Cubs, and Blackhawks. He also will be a temporary fan of any team if it means winning him bets.

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