The top 5 Best MLB Trade Deadline Trades of All Time

The top 5 Best MLB Trade Deadline Trades of All Time

The top 5 Best MLB Trade Deadline Trades of All Time

Photo by MIKE FIALA/AFP via Getty

The MLB Trade Deadline is a turning point for many major league teams which often turn things around with different chances to work their rosters. In this post, we countdown the top five MLB trade deadline deals in league history as well as evaluate both team transactions and player movements of such monstrous proportions.

1. Randy Johnson to the Houston Astros (1998)

  • Teams Involved: Houston Astros, Seattle Mariners
  • Players Traded: Randy Johnson (to the Astros), Freddy Garcia, Carlos Guillen (to the Mariners)

Context and Circumstances

The Astros were busy trying to compete for a playoff push and certainly needed an ace. The Astros traded for Johnson just before the start of the July 31st deadline, sending Freddy Garcia and Carlos Guillen to Seattle in exchange.

Analysis of the Trade

It is considered by many one of the greatest trades in MLB history based on Johnson's immediate success. He joined the Astros and went 10-1 with a minuscule ERA of just above 1.00 in 11 starts, which took them to the NL Division Series. Even in a playoff defeat, Johnson's showing further established him as one of the top pitchers on the planet.

Garcia and Guillen were central players for the Mariners during those years, highlighted by their 116-win season in but Johnson was a big trade that marked an Astros team not afraid to go all-in on winning. It would end up being just the first of many Cy Young Awards Johnson won, validated him as a Hall of Famer and added to mythos.

2. Nomar Garciaparra, Chicago Cubs (2004)

  • Teams Involved: Boston Red Sox, Chicago Cubs, Montreal Expos, Minnesota Twins
  • Players Traded: Nomar Garciaparra - Chicago Cubs
  • FLoip LHPs : Orlando Cabrera and Doug Mientkiewicz (to the Red Sox)

Context and Circumstances

The 2004 trade deadline brought several trades that were set in motion halfway around the league, but its biggest deal was arguably a four-team blockbuster headlined by the swap of Red Sox icon Nomar Garciaparra to the Cubs. The Boston Red Sox were hoping to change their fortunes after a lengthy title drought. 

Analysis of the Trade

The deal is looked back upon favorably because of how quickly it helped Boston win games. Cabrera at short and Mientkiewicz as a late-game pinch hitter helped the Red Sox lock down their first World Series title in 2004. The trade was a fateful moment in Red Sox history as Garciaparra, although still productive with the Cubs, never did make it back to meaningful postseason action.

3. CC Sabathia - Milwaukee Brewers (2008)

  • Teams Involved: Cleveland Indians, Milwaukee Brewers
  • Players Traded: CC Sabathia (to the Brewers), Matt LaPorta, Michael Brantley, Zach Jackson, Rob Bryson (to the Indians)

Context and Circumstances

The Brewers were in the thick of a playoff chase, front-ending their rotation was among their primary needs and they would compete mightily but eventually fall short of contention later that season. The Indians sent ace CC Sabathia to the Brewers after deciding they needed a full overhaul in exchange for prospects. When healthy, Sabathia was in the midst of a Cy Young-caliber season and thus one of baseball's most sought after assets.

Analysis of the Trade

The effect of Sabathia was immediate and far-reaching. He went 11-2 with a 1.65 ERA in 17 starts for the Brewers, who made it to the playoffs that season for the first time since '82. It secured his team a Wild Card spot, and it solidified one more trait of CC's game: the ability grind through high-leverage situations.

The Indians, of course, have gotten a ton out of the deal as well, with Michael Brantley eventually solidifying himself into an All-Star caliber outfielder for them in addition to their prospects. The long term implications aside what Sabathia did that summer was historic and made this one among baseball's most unforgettable trades ever. This was never more apparent than when he joined the starting rotation down the stretch in 2010, and suddenly, one player could turn around an entire team's fortunes.

4. Manny Ramirez to the Los Angeles Dodgers (2008)

  • Teams Involved: Boston Red Sox, Los Angeles Dodgers
  • Players Traded: Manny Ramirez, Dodgers, Jason Bay (to the Red Sox)

Context and Circumstances

The Red Sox wanted to shake up their roster in 2008 and were not getting on with Manny Ramirez. The Dodgers sought help in the power department. It was also a three-team trade that the Dodgers got in on, acquiring Ramirez and turning him into an instant success.

Analysis of the Trade

Manny vibrated through the Dodgers like lightning. He hit .396 with 17 home runs and 53 RBIs in only fifty-three games, propelling the Dodgers into postseason play while earning NL Player of the Month recognition on multiple occasions.

The Red Sox got Jason Bay, who did not slump for years afterward and was overshadowed when he played in Boston because the deal would go down as that time Manny Ramirez turned into a god among mortals out west. It was proof of a player with such immense gifts, when paired with the best team in baseball could shift everything and provide jolt to an organization.

5. Max Scherzer and Trea Turner, Los Angeles Dodgers (2021)

  • Teams Involved: Washington Nationals, Los Angeles Dodgers
  • Players Traded: Max Scherzer and Trea Turner (to LAD), Josiah Gray, Keibert Ruiz and others (to NATS)

Context and Circumstances

Going into the 2021 trade deadline, Scherzer and Turner were two of Washington's top bargaining chips as they drifted through a rebuild. Both players were traded in a classic July deadline deal that saw the Dodgers make an aggressive bid to strengthen their roster for a run at the playoffs.

Analysis of the Trade

However, the trade to acquire both Scherzer and Turner was a game changer for the Dodgers. Scherzer, a future Hall of Famer, supplied an ace for the rotation while Turner brought speed and flexibility into the lineup. Together, the two led to a Dodgers playoff berth and a long postseason run.

Though the Washington Nationals netted a pair of blue-chip prospects from Los Angeles, Scherzer and Turner immediately made this deal one excellent trade for MLB posterity, at least in terms of how it helped bring home another trophy to Chavez Ravine. All three of these players played an important role in the Dodgers' journey to yet another championship, which is amazing how small acquisitions can ultimately change a team's fate.


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