Manny Machado is reportedly a Dodger, likely taking this year’s biggest trade chip off the market. However, you never know what’s going to happen in advance of the MLB non-waiver trade deadline. The Machado trade immediately registers as one of the biggest deadline deals of the last 20 years, but everyone knew from the time the first pitch of the 2018 season was thrown that he wouldn’t end this year with the Orioles. That isn’t the case of every trade made at the deadline.
With that, we present the five biggest trade deadline moves going back to 1998. You want a deal that makes the baseball world stop in its tracks? These ones did just that.
5. Carlos Beltran to the Astros, June 24, 2004
By 2004, Beltran had developed into one of the brightest stars in baseball. He was working on his fourth straight season with at least 24 homers, 30 steals, 100 RBI and a .500 slugging percentage, and it was looking like it would be his best yet. He was also an impending free agent and it was clear that the Royals were not going to meet his contract demands in the offseason. This transaction came across the wires as a major shock, though, given that there were still more than five weeks until the deadline. The Astros swooped in as part of a three-team deal with the Royals and A’s that netted the Royals Mark Teahen, Mike Wood and John Buck. All they had to give up to secure Beltran’s services was Buck and Octavio Dotel.
Beltran was hitting .278/.367/.548 with 15 homers, 14 steals and 51 RBI at the time of the trade. He’d go on to slash .258/.368/.559 with 23 bombs, 28 steals and 53 RBI, lifting the Astros from fifth place in the NL Central on the day of the trade (though just five behind first-place St. Louis) to a 92–70 record and the NL Wild Card. The Astros would eventually lose to the Cardinals in the NLCS, but Beltran was fantastic in that series, going 10-for-24 with four homers, four steals and eight walks in the seven games.
4. David Price to the Blue Jays and Yoneis Céspedes to the Mets, July 30 and 31, 2015
The Tigers sat at 49–52 on July 29, 2015, 3.5 games behind the Twins for the second Wild Card in the AL. It wasn’t the season the team expected to have, but there was still good reason for optimism. Céspedes, Miguel Cabrera and J.D. Martinez were all having excellent seasons. Price was in the midst of a year in which he would finish second in AL Cy Young voting. And after missing the first 10 weeks of the season with an injury, Justin Verlander was back and starting to round into form. It may have been a slog through the first half of the year, but the second half could potentially be special.
And then, they blew it all up. They started by sending Price to the Blue Jays on July 30 for Daniel Norris, Matt Boyd and Jairo Labourt. The next day, after some serious “will-they-or-won’t-they” intrigue, they dealt Céspedes to the Mets for Michael Fulmer and Luis Cessa. At the time of their respective trades, neither the Blue Jays nor Mets were that much better than the Tigers by win-loss record. The Blue Jays were 51–51, while the Mets were 52–50. They would go in radically different paths the rest of the season.
The Tigers ended the year at 74–87, last place in the AL Central. The Blue Jays and Mets, on the other hand, won their respective divisions, with the Mets surging to the World Series where they fell to the Royals in five games. Price was just as good for the Blue Jays as he was for the Tigers, going 9-1 with a 2.30 ERA, 1.01 WHIP and 87 strikeouts in 74 1/3 innings across 11 starts. Céspedes, meanwhile, hit .287/.337/.604 with 17 homers and 44 RBI in 57 games with the Mets. He liked his time so much, that he signed with the team as a free agent in the offseason.
3. Manny Ramirez to the Dodgers, July 31, 2008
The second of three deadline day deals that made the cut, Ramirez making the cross-country trip to Los Angeles from Boston was momentous on both coasts. In the East, it advanced the turning of the page from Boston’s curse-breaking era. David Ortiz, Tim Wakefield and Jason Varitek were still there, but Ramirez joined Pedro Martinez, Curt Schilling, Johnny Damon, Kevin Millar and Keith Foulke as the heroes of ’04 who were then former Red Sox. In Los Angeles, meanwhile, it signaled that the Dodgers, who were then just one game over .500, were all-in on the 2008 season.
Ramirez may have been 36 years old at the time, but he still mashed with the best of them. He hit .299/.398/.529 with 20 homers before the trade. That somehow paled in comparison to what he did once he put on the Dodger blue. In 229 plate appearances across 53 games with the Dodgers that season, Ramriez slashed .396/.489/.743 with 17 homers and 53 RBI. He was just as good in the postseason, going 5-for-10 with two homers and four walks in a three-game sweep of the Cubs in the NLDS, and 8-for-15 with two more jacks, seven walks, and seven RBI in the five-game NLCS loss to the Phillies.
2. CC Sabathia to the Brewers, July 7, 2008
This one happened well before the deadline, but that doesn’t mean it was any less astounding when it went down. After blowing a 3–1 lead in the ALCS to the Red Sox the previous season, the Indians had bottomed out, and were in last place in the AL Central at the time of the trade. Sabathia was an impending free agent, and it was already clear 2008 would be his last year in Cleveland. This trade, more than three weeks before the deadline, hit like a thunderbolt in a crowded NL Central race.
The Cubs entered play on July 7 at 53–36, 3.5 games ahead of both the Cardinals and Brewers. The trade spurred the Cubs to answer the very next day by trading for Rich Harden. The Brewers, meanwhile, were trying to end a postseason drought that stretched back to 1982, when they lost to the Cardinals in what is still the franchise’s only World Series appearance. Adding Sabathia made that all the more possible.
Sabathia was in solid, though substandard, form at the time of the trade, pitching to a 3.83 ERA and 1.23 WHIP in 122 1/3 innings with the Indians. He was lights out from the moment he put on a Brewers uniform, going 11-2 with a 1.65 ERA, 1.00 WHIP and 128 strikeouts in 130 2/3 innings across 17 starts. He threw seven—seven!—complete games with Milwaukee, including three shutouts. It was fitting, then, that he was on the mound when the team clinched the Wild Card and its first trip to the postseason in 26 years.
1. Randy Johnson to the Astros, July 31, 1998
Seattle’s trade of the Big Unit to the Astros, which happened nearly 20 years ago and just barely makes the cut, remains the standard in monster deadline deals. The fact that it was a deadline day deal gives it bonus points. This one truly went down to the wire. The Astros were clearly a World Series contender, but, at 64–44 entering the day of the trade, they had the worst record among NL division leaders, trailing the 72–37 Braves and 70–38 Padres. They were also just 3.5 games ahead of the Cubs in the Central. Adding Johnson instantly gave them breathing room in their own division, and brought them even with, if not ahead of, the Braves and Padres.
Nevermind that Johnson was 9–10 with a 4.33 ERA and 1.29 WHIP at the time of the trade; he was still one of the most feared, dominant pitchers in the majors. He went on to carry Houston to a 102-win season, going 10–1 with a 1.28 ERA, 0.98 WHIP and 116 strikeouts in 84 1/3 innings across 11 starts. The Astros lost to the Padres in the NLDS and Johnson signed with the Diamondbacks in the offseason, but the trade will always be remembered as one of the most momentous deadline deals in MLB history.
This one also gets bonus points because it happened way back in the 90s. There was no constant news cycle. There was no Twitter or MLBtraderumors.com. In-home internet was still in its nascent stages. At one point on July 31, 1998, there was no news for the regular civilian about Johnson, and then suddenly he was an Astro, shifting the balance of power in the NL. That’s what a huge deadline deal is all about.