Best MLB Trade Deadline Deals Of All-Time


Major League Baseball’s non-waiver trade deadline is at 4 p.m. ET on Monday. The fortunes of contending teams can often change dramatically thanks to last-minute deals, and this year should be no different.

With that in mind, here’s a look at the 10 best, most impactful deadline deals in baseball history. Some of which wound up working out for both teams involved.

Cespedes Goes to the Big Apple

The New York Mets needed a bat at the 2015 trade deadline and they landed a big one when they sent Michael Fulmer and Luis Cessa to the Detroit Tigers in exchange for Yoenis Cespedes. In his first 41 games for the Mets, Cespedes hit .309, with 17 home runs and 42 RBI while slugging .691. All-in-all, he finished his final 57 games of the season he posted an OPS of .941 and posted 66 hits.

Cespedes helped the Mets to the World Series, where they lost to the Kansas City Royals. Unfortunately, he hit just .150 in the series, and his 17 total postseason strikeouts were awful. Still, without Cespedes, the Mets don’t make that World Series.

Meanwhile, the Tigers didn’t do poorly, as Fulmer has the makings of an ace at just 24 years old.

The Big Unit heads to the Lone Star State

This is another deal that worked out for both teams in the long run, but the Houston Astros had to add a starting pitcher in 1998, and they unloaded a ton to secure one. Randy Johnson was sent to Houston in exchange for Freddy Garcia, John Halama and Carlos Guillen.

Johnson went 10-1 with a 1.28 ERA and four shutouts in 11 starts. He also struck out 116 hitters in 84.1 innings. The Big Unit was flat out amazing and the Astros won the National League Central on his back. Unfortunately, Houston lost Johnson’s two postseason starts (Game 1 and Game 4) in the NLDS to the San Diego Padres. He left in free agency after the season, but man was he phenomenal for the Astros. He finished 7th in NL Cy Young voting despite only being on the team for 11 starts.

Meanwhile, Garcia and Halama combined to go 28-13 and Guillen was the starting shortstop for the Mariners team that won 116 games in 2001. The trio also combined for a 33.3 WAR as members of the Mariners.

LA turns into Mannywood

The Boston Red Sox were ready to move on from Manny Ramirez and they did so on July 31, 2008. In a three-way trade the Los Angeles Dodgers got Ramirez, Andy LaRoche, Bryan Morris, Craig Hansen and Brandon Moss went to the Pittsburgh Pirates and Jason Bay went to the Red Sox.

Ramirez played 53 games during the rest of 2008 and exploded. He posted a .396/.489/.743 slash line, and had 17 home runs, 53 RBI and posted an OPS of 1.232. In eight postseason games, Ramirez hit .520 with four home runs, 10 RBI and 11 walks again four strikeouts. He also had an unholy OPS of 1.747. Were those numbers crazy for a 36-year-old? Yes. Were they steroids-fueled? Almost certainly. But still, the results are what mattered and Ramirez provided them.

Bay won a Silver Slugger and was an All-Star in 2009, but the Dodgers won this deal by a long-shot.

Diamondbacks get a Schill

The Arizona Diamondbacks landed Curt Schilling on July 26, 2000 and paired him with Randy Johnson to form one of the best pitching duos in baseball history. Schilling went 5-6 with a 3.69 ERA and a 1.10 WHIP in 2000, but the next year is where things took off.

Schilling went 22-6 with a 2.98 ERA and a 1.08 WHIP and had 293 strikeouts in 256.2 innings. He and Johnson also led the Diamondbacks to a seven game win over the New York Yankees in the 2001 World Series.

The Philadelphia Phillies received Travis Lee, Omar Daal, Vicente Padilla and Nelson Figueroa in exchange for Schilling. It’s clear the Diamondbacks got the better of the swap.

The Brew Crew gets a big man

CC Sabathia was set to hit free agency after the 2008 season, but the Milwaukee Brewers went all-in for him. They sent Matt LaPorta, Zach Jackson, Rob Bryson and Michael Brantley to the Cleveland Indians in exchange for Sabathia, who was outstanding down the stretch.

In the span of 83 days, Sabathia threw a ridiculous 130.2 innings. He went 11-2 with a 1.65 ERA, a 1.00 WHIP, with 128 strikeouts against just 25 walks. He threw seven complete games and had three shutouts. He led the Brewers to a Wild Card berth and their first postseason appearance since 1982.

The Brewers lost to the Phillies in the NLDS, but Sabathia was everything Milwaukee asked for and more.

Nomah! Helps the Red Sox win the World Series…from Chicago

The Red Sox were in a funk as the trade deadline approached in 2004, and given the drama surrounding former star Nomar Garciaparra, they needed to make a move. So Theo Epstein did the unthinkable, and unloaded Nomar in a four-team deal that netting the Red Sox both shortstop Orlando Cabrera (from the Montreal Expos) and first baseman Doug Mientkiewicz (from the Minnesota Twins). Garciaparra wound up with the Cubs, along with Matt Murton.

Cabrera and Mientkiewicz solidified Boston’s heretofore atrocious infield defense and the Red Sox wound up taking the AL wild card spot by seven games over the A’s.

The Garciaparra trade was the turning point of that season, as the Red Sox became a truly formidable team. As we all know now, they went on to win their first World Series since 1918 and broke the Curse of the Bambino. Mientkiewicz made the final putout in the clinching World Series game.

Beltran lights up Houston

Carlos Beltran landed in Houston from the Kansas City Royals in a three-way deal that saw the Astros shipping out Octavio Dotel to the Oakland Athletics and John Buck to K.C. Houston got so much out of Beltran after they acquired him on June 24, 2004.

Beltran played in 90 games for the Astros in 2004, he hit .258 with 23 home runs, 53 RBI and 23 stolen bases. He slugged .559 and had an OPS of .927. While that was great, he absolutely exploded in the postseason. In 12 playoff games he hit .435, with a postseason-record eight home runs, 14 RBI and an insane OPS of 1.557.

The Astros lost to the St. Louis Cardinals in seven games in the NLCS, but they certainly got their money’s worth with Beltran.

Sut heads to the North Side

On June 13, 1984, the Chicago Cubs acquired a big piece to their playoff puzzle. The Cubbies landed ace righty Rick Sutcliffe from the Indians in exchange for a package that included Joe Carter. Chicago was in first place at the time of the trade but needed a true ace. Sut fit the bill.

“The Red Baron” was 4-5 with the Indians, but caught fire with the Cubs. He went 16-1 the rest of the way, with a 2.69 ERA, 1.08 WHIP and 155 strikeouts in 150.1 innings. He was the unanimous choice for the NL Cy Young Award and took the victory in Game 1 of the NLCS and hit a home run during the contest.

Obviously Carter would go on to have a decorated career, but he never went to an All-Star Game as a member of the Indians (1984-1989, though he did lead the AL in RBI in 1986.

Oswalt goes to Philly

The Philadelphia Phillies had gone to back-to-back World Series heading into the 2010 trade deadline, but felt their rotation needed more help. So they sent J.A. Happ, Anthony Gose and Jonathan Villar to the Houston Astros in exchange for Roy Oswalt just before the deadline. It wound up paying off after Oswalt waived his no-trade clause to consummate the deal.

Before the trade, Oswalt was 6-12 with a 3.42 ERA and a 1.11 WHIP. After landing in Philly he took off, posting a 7-1 record with a stellar 1.74 ERA, a 0.90 WHIP and 73 strikeouts against 21 walks in 82.2 innings. In four postseason appearances (three starts) he went 1-1 with a 2.75 ERA, 1.17 WHIP and 19 strikeouts in 19.2 innings.

The Phillies didn’t return to the World Series in 2010, as they lost to the San Francisco Giants in the NLCS. But Oswalt was marvelous after the trade and a big part of Philadelphia winning its third NL East crown in a row.

Happ never truly developed in Houston and has bounced around the league since, having a decent season here and there. Gose is now trying his hand at pitching in the Detroit Tigers organization and Villar is now in the middle of a disappointing season with the Brewers.

Andrew Miller gives the Tribe a bullpen cornerstone

The Indians desperately needed a high-leverage bullpen arm down the stretch in 2016 and it cost them big-time to land one. They sent Clint Frazier, Justus Sheffield, J.P. Feyereisen and Ben Heller to the Yankees in exchange for lights-out lefty Andrew Miller. This is a trade that worked out for both sides, especially since Miller was under contract for three more years.

Miller was electric after the deal. He went 4-0 with three saves while striking out 46 and walking just two in 29 innings. Over the course of 26 games he posted an ERA of 1.55 and a ridiculous WHIP of 0.55. In the postseason he was absolutely dominant. Miller threw a record 19.1 relief innings over 10 playoff games and posted a 1.40 ERA, 0.88 WHIP and had 30 strikeouts against just five walks. He also went 2-0 with a save and allowed just 12 hits. He was the ALCS MVP and likely would have been the World Series MVP had the Indians bested the Cubs in Game 7.

Meanwhile, Frazier has lived up to his billing as a top prospect, as the 22-year-old has been solid since finally getting a call-up this summer. Time will tell on the other three players the Yankees received.

While the Miller acquisition may not seem huge in hindsight, he absolutely changed the way the Indians played games. He was a multi-inning reliever who took an enormous amount of pressure off of the team’s injured starting rotation. With Carlos Carrasco and Danny Salazar both injured, the team’s bullpen had to step up. Miller led the way.