2019 MLB trade deadline retrospective: Revisiting the Zack Greinke blockbuster, Nick Castellanos swap, more

The 2024 MLB trade deadline is one week and four days away, but the action has already begun. Luis Arraez was traded more than two months ago now, and in recent weeks we’ve seen other deals involving Aaron Civale and Hunter Harvey. There will be more trades between now and then. Many more, I assure you.

After the trade deadline, we’ll rush to judgment and anoint winners and losers. There’s value in evaluating things based only on what we know at the time. There’s also value in looking back and seeing how things played out, and that’s what we’re going to do now. We’re going to get in the time machine, go back five years, and look at what happened at the 2019 deadline.

Five years isn’t that long ago in the grand scheme of things but it is an eternity in baseball years. The Wild Card Game was still a thing in 2019, so there were fewer postseason spots and also a greater incentive to win the division. I miss the Wild Card Game, honestly. It was Game 7 without the fuss of Games 1-6.

Anyway, let’s go back and examine the 2019 trade deadline, shall we? Here are the biggest moves, the not-so-big moves, and a five-years-too-late scolding of the teams that didn’t do enough.

The last-minute blockbuster

Astros get: RHP Zack Greinke and $24 million
Diamondbacks get: 1B/OF Seth Beer, RHP JB Bukauskas, RHP Corbin Martin, UTIL Josh Rojas

The biggest trade of the 2019 deadline came in after the buzzer. The trade was reported after the deadline — it was completed with the league before the clock ran out, of course — and it was a blockbuster. The Astros added Greinke, who to that point had made 23 starts with a 2.90 ERA, to a stacked rotation that already included Gerrit Cole and peak Justin Verlander.

“A little reminiscent of the (Verlander trade in 2017) and obviously with a hard deadline this year, it was important we get something done,” then-GM Jeff Luhnow said after the trade (via MLB.com). “… For us, Zack Greinke was at the very top of our list in terms of players that we thought could impact our chances to win the World Series this year and could really fit in well on this club for the next couple of years while we still have our entire offensive unit together.”

Houston had a comfortable 7.5-game division lead on the morning of the trade deadline. Adding Greinke was not about winning the AL West or getting to the postseason. The Astros brought in Greinke to put them over the top in October. To give them a fearsome 1-2-3 rotation punch with Cole and Verlander. Three Hall of Fame talents, all of whom were at the top of their game at the time.

A rotation addition was necessary too. Cole and Verlander were great, obviously, and Wade Miley was a fine No. 3. Otherwise, the Astros had cycled through No. 4 and 5 types all season. Cole, Verlander, and Miley led the team in starts. Brad Peacock was fourth with 15 starts. Greinke’s 10 regular season starts were the fifth most on the club. He halted the revolving door.

In those 10 regular season starts, Greinke pitched to a 3.02 ERA, and the Astros cruised to the division title. His postseason was a bit more uneven: 4.68 ERA in five starts, though he was excellent in Game 7 of the World Series. Greinke held the Nationals to two runs in 6 2/3 innings on only 80 pitches, and exited with a one-run lead. He did his job that night. The bullpen did not.

Greinke had two years remaining on his contract at the time of the trade and 2020-21 didn’t go quite as well: 4.12 ERA and 2.3 WAR in 238 innings. Solid production, but not a frontline starter. The priority was elevating the 2019 team and Greinke did that even though the Astros fell short in the World Series. The next two seasons were something to worry about later.

For the D-backs, the trade was as much about clearing payroll as accumulating talent. They were 16.5 games behind the Dodgers at the deadline and 3.5 games behind the second wild-card spot, though there were four teams ahead of them. Simply put, the club was not playing well. The D-backs lost 21 of their 38 games leading up to the trade deadline.

The four players Arizona received in the trade were all solid prospects, and all four would eventually play in the big leagues with the D-backs, though only Rojas had staying power. The Diamondbacks covered $24 million of the $77 million or so remaining on Greinke’s contract, so all told, the trade netted them four young players and $53 million in savings spread across 2019-21.

“I know where we are relative to the standings. We haven’t played very well recently,” D-backs GM Mike Hazen said after the trade (via the Arizona Republic). “But I also feel like we were able to satisfy some longer-term needs — spread out some of those needs — while at the same time we didn’t touch our position player group. And we feel like this team has a chance to compete.”

The D-backs backfilled Greinke’s innings by bringing in veteran Mike Leake in a trade with the Mariners and, to their credit, they did not pack it in after the deadline. Arizona went 31-22 the rest of the way and ultimately ended the year with an 85-77 record. They finished four games out of a wild-card spot. Do they make the postseason if they keep Greinke? I don’t think so but I can’t say for certain.

To their credit, the D-backs put the cash savings back into the roster, just not in the best way. A few weeks after Greinke and the Astros lost the World Series, the Diamondbacks signed Madison Bumgarner to a five-year, $85 million contract. It was reported at the time that ownership drove the signing, not Hazen. Bumgarner had a 5.23 ERA with Arizona before being released last April.

In the end, the D-backs turned Greinke into Rojas and however much of the Bumgarner signing you want to attribute to the cash savings. Arizona did that while Greinke helped the Astros get to within a few outs of a World Series championship. I think we can all agree which side won this trade. The D-backs weren’t wrong to trade Greinke. It just didn’t work out all that well. So it goes.

The missing piece

Nationals get: RHP Daniel Hudson
Blue Jays get: RHP Kyle Johnston

The pitcher who threw the first pitch of Game 7 of the World Series was traded at the deadline (Greinke) and so was the pitcher who threw the last pitch of Game 7 of the World Series. The Nationals lost 31 of their first 50 games in 2019 and there were rumblings they could sell at the deadline. Instead, they got molten hot during the summer, and became buyers come deadline time.

Bullpen help was an obvious need and, to bolster the relief unit, the Nationals picked up Hudson in a trade with Toronto. The veteran rental had a 3.00 ERA for a Blue Jays team that eventually lost 95 games. With Washington, Hudson had a 1.44 ERA during the regular season, and went 4 for 4 in save chances in October. Seven of his nine postseason appearances were scoreless.

With a 6-2 lead in Game 7, Hudson was called upon to pitch the ninth inning, and he went 1-2-3 with a pop up (George Springer) and two strikeouts (Jose Altuve and Michael Brantley) to secure the first World Series title in Expos/Nationals franchise history. Who saw that coming when the trade was made?

Johnston, a sixth round pick in 2017, was in Single-A at the time of the trade. He reached Triple-A with Toronto in 2021 but never made it to the big leagues. He currently pitches for the Cleburne Railroaders of the independent American Association.

The great trade that still wasn’t enough

Cubs get: OF Nick Castellanos
Tigers get: RHP Alex Lange, RHP Paul Richan

After the 2016 World Series, it was easy to think the Cubs had a chance to be a dynasty given how young and talented their roster was at the time. It didn’t work out that way. Chicago lost the NL Wild Card Game in 2018 and, on the morning of the 2019 deadline, they were a game behind the Cardinals in the NL Central and in a virtual tie for the second wild-card spot. They were just trying to get into the postseason. So, to bolster their offense, they picked up Castellanos, a rental, from the Tigers.

Castellanos was everything the Cubs could have hoped after the trade. He slashed .321/.356/.646 with 16 home runs in 51 games with Chicago, but it still wasn’t enough. The Cubbies had a worse record and scored only slightly more runs per game after the trade than before:

Castellanos held up his end of the bargain. He was great. The rest of the Cubs were not. Chicago went from tied for the NL Central lead on deadline day to finishing seven games out in the division, and missing a wild-card spot by two games. Castellanos had the desired impact but it wasn’t enough to get the Cubs into the postseason. He signed with the division rival Reds after the season. 

As for the Tigers, Richan never made it to the big leagues, and Lange reached the show in 2021. He’s been a mostly solid bullpen option (occasionally great, occasionally terrible) who saved 26 games in 2023. All things considered, turning one of the top rental bats at the 2019 deadline into a good but not great reliever is an L for the Tigers. Castellanos put up 1.8 WAR in 51 games with the Cubs. Lange is at 1.4 WAR in parts of four seasons with Detroit.

The challenge trade

Marlins get: SS Jazz Chisholm Jr.
Diamondbacks get: RHP Zac Gallen

The D-backs were very active at the deadline. They unloaded Greinke on the Astros just before the buzzer, picked up Leake to fill the rotation spot, and also made one of the most fun trades in recent memory: Chisholm for Gallen, straight up, one for one. The rare prospect for prospect trade. Gallen did make his MLB debut earlier that year and had made seven starts with Miami, though he was still rookie-eligible and thus prospect-eligible at the time of the trade. Prospects are like children, you love yours more than you love everyone else’s, so prospect for prospect trades are extremely rare.

“We like his ability to throw strikes,” Hazen said about Gallen after the trade (via MLB.com). “We like his ability to pitch. We like his ability to strategize. He’s got good secondary stuff. We think he’s durable. He does a lot of things that we like in a starting pitcher.”

“I think you can put whatever ceiling you want on him,” Marlins then-GM Michael Hill said about Chisholm (via the Miami Herald). “When you talk about his tool package and what he brings to the table, it’s Gold Glove defense. It’s power from a position that you don’t expect power from. It’s athleticism. I think the sky’s the limit when you talk about what he can do on a baseball field.”

Each team traded from a position of depth to address a weakness. The D-backs were about to add Rojas and had Geraldo Perdomo coming, so the infield was not a top priority. They needed arms. The Marlins were blessed with a ton of young pitching (Sandy Alcantara, Braxton Garrett, Edward Cabrera, Trevor Rogers, and Sixto Sánchez were all in the farm system at the time), so they used some of it to land the high-upside bat they lacked. An old-school challenge trade.

It’s fair to say the D-backs are winning this trade, not that Chisholm has been a dud. He’s gone to an All-Star Game (2022) and has been an above-average hitter these last three years. Injuries have slowed him a bit though, and he’s shifted from shortstop to second base to center field. Chisholm is still only 26 and under team control through 2026, so there’s plenty of time for him deliver on his talent. That said, the Marlins are yet again rebuilding. Chisholm is trade bait at the moment.

Gallen, meanwhile, has become one of the best pitchers in baseball with Arizona. He’s received Cy Young votes in three seasons and has two top-five finishes in the voting (2022 and 2023). He’s been roughly 30% better than the league average pitcher with the D-backs once adjusted for ballpark and other factors. Gallen has more than doubled Chisholm’s WAR since the trade and he’s still under team control through 2025.

So many trades these days are prospects for big leaguer, and I get it. Rebuilding teams sell and want prospects, contenders want to upgrade their MLB roster without sacrificing pieces. It’s sensible. And it happens so much that big leaguer for big leaguer trades have a little extra juice, and prospect for prospect trades even more. We almost never see them. It happened at the 2019 trade deadline though. Chisholm for Gallen in the most notable prospect for prospect trade in recent memory.

Buying and selling at the same time

Cleveland gets: LHP Logan Allen, LHP Scott Moss, OF Yasiel Puig, OF Franmil Reyes, 3B Victor Nova
Reds get: RHP Trevor Bauer
Padres get: OF Taylor Trammell

On the morning of the 2019 deadline, the Padres (50-57) and Reds (49-56) were out of the postseason race and building toward the future, Cincinnati for 2020, San Diego more long-term. Cleveland was three games behind the Twins in the AL Central and in the top wild-card spot, though three other teams were within four games. In theory, they had pitching to trade, and they needed offense. The rotation depth chart at the time looked like this:

1. RHP Corey Kluber (out until August with a broken arm)
2. RHP Trevor Bauer
3. RHP Carlos Carrasco
4. RHP Shane Bieber
5. RHP Mike Clevinger
6. RHP Danny Salazar (would make 2019 debut a few days after the deadline)
7. RHP Zach Plesac (debuted that May)

Carrasco and Kluber were beginning to age out as elite pitchers, but Bieber and Clevinger (and to a lesser extent Plesac) were fully breaking out, so the rotation was in good hands. Up to that point in his career, Bauer was maddeningly inconsistent. Had a few stretches that put him among the best pitchers in the game, and other stretches when he was only so-so. He had a 3.74 ERA in 24 starts before the trade. 

Trading a starter for a bat made sense for Cleveland at the deadline and Bauer was an obvious candidate to go. Not only was it no secret Cleveland would be unable to re-sign him as a free agent after 2020, but Bauer was frustrating coaches and manager Terry Francona. The final straw seemed to happen on July 28, when Bauer got tagged for eight runs in 4 1/3 innings in Kansas City. He was upset when he got pulled and threw the ball over the center field wall. Remember this?

Three days later, Cleveland traded Bauer to the Reds for the above package of five players. Just to sort it all out: The Reds traded Moss, Trammell, and Puig for Bauer. The Padres traded Allen, Nova, and Reyes for Trammell, who was considered one of the 25 or so best prospects in the game at the time. Cleveland used their rotation depth to add two MLB bats (Puig and Reyes) and bolster their organizational depth. San Diego added a top-flight prospect. The Reds got Bauer to help them contend in 2020.

“Over the last several weeks, we explored the trade market in an effort to enhance our competitive position, both by supplementing our Major League roster and infusing young talent into the organization,” Indians POBO Chris Antonetti said in a statement after the trade. “We appreciate Trevor’s contributions to the organization in his time with us, and while it’s never easy to part with a player of his caliber, we feel we’ve traded from an area of depth to help bolster our Major League club for this year and the foreseeable future.”

At the time of the trade, Cleveland was tenth in the American League in runs scored and ninth in slugging percentage. They badly needed an infusion of power. Puig, a rental, hit 22 homers in 100 games with the Reds. Reyes came with long-term control and had slugged 43 home runs in 186 games with the Padres from 2018-19, though he was essentially a full-time DH. Puig brought some defensive value in the outfield. As for how things played out, what do you think? Here are their numbers after the trade:

Reyes provided power and not much else. Puig hit 22 home runs with the Reds and then only two with Cleveland, though he did hit for average and get on base. Cleveland finished the season eighth in runs and sixth in slugging percentage in the AL, so the offense did tick up after the trade. It wasn’t enough to get them to the postseason though. Cleveland went 30-25 after the deadline and was unable to pass the Twins in the AL Central or secure a wild-card spot. They missed the postseason for the first time since 2015.

Puig departed as a free agent after the season while Reyes slugged 58 home runs in parts of four seasons with Cleveland. Allen showed promise early in his career but never did carve out a long-term role. Moss and Nova have yet to reach the big leagues. For all intents and purposes, Cleveland traded a year and a half of Bauer for half a year of Puig and parts of four seasons of Reyes. They also saved money by trading Bauer, and rid themselves of player who had become a headache. Cleveland was a buyer and a seller at the 2019 deadline. They subtracted from their rotation to improve the lineup.

Bauer won the NL Cy Young during the pandemic-shortened 60-game season with Cincinnati in 2020 and helped the Reds reach the postseason, though they were swept in the Wild Card Series. When he left as a free agent after 2020, the Reds received the No. 30 pick in the 2021 draft as compensation. They used that pick on high school outfielder Jay Allen, who MLB Pipeline ranks as the organization’s No. 24 prospect. Long story short, the Reds gave up nothing they miss and got a Cy Young season from Bauer. That worked out as intended even if it didn’t lead to any postseason success.

Trammell’s stay in San Diego was short. He never played in the big leagues with the Padres and they traded him to the Mariners at the 2020 deadline in the big Ty France/Andrés Muñoz/Austin Nola deal. Trammell’s been unable to carve out a big-league role and has bounced around on waivers. The Padres were the third wheel in this trade.

Other notable trades

Mets, Blue Jays make a win-win trade: It was no secret Marcus Stroman hoped to land with the other New York team at the 2019 deadline, but he wound up with the Mets, and proceeded to talk trash about the Yankees on social media in the following weeks. (The two sides buried the hatchet this offseason.) Ultimately, this trade worked out nicely for both teams. The Mets got Stroman, who pitched to a 3.21 ERA from 2019-21 (he opted out of the 2020 pandemic season), and the Blue Jays received pitching prospects Anthony Kay and Simeon Woods Richardson. Woods Richardson was later used to acquire José Berríos. 

A’s beef up their rotation: The Athletics are a laughing stock now, but between 2012 and 2020, only the Dodgers made more trips to the postseason. On the morning of June 14, the A’s were one game out of a wild-card spot. Later that day, they sent infield prospect Kevin Merrell to the Royals for Homer Bailey, then on deadline day they sent outfield prospect Jameson Hannah to the Reds for Tanner Roark. Roark was heading to Atlanta for the Reds’ upcoming series with the Braves when he found out about the trade.

Bailey and Roark combined to make 13 starts with a 4.42 ERA for the A’s. That was a huge upgrade over the guys they replaced: Tanner Anderson, Aaron Brooks, Marco Estrada, and Daniel Mengden had a 5.90 ERA in 37 starts in 2019. The A’s did reach the postseason thanks in part of Bailey and Roark. Alas and alack, they lost to the Rays in the Wild Card Game. Neither Hannah nor Merrell has reached the big leagues.

The annual Marlins-Rays trade: Doesn’t it seem like these two teams make a trade every few months? They’ve made nine trades since 2019. This one sent righties Nick Anderson and Trevor Richards to Tampa for righty Ryne Stanek and outfield prospect Jesús Sánchez. Anderson became one of the best relievers in the game for a few years after this trade, though he’s perhaps best remembered for blowing Game 6 of the 2020 World Series after Blake Snell was pulled early. Anderson allowed nine runs in 14 2/3 innings that October. Richards was sent to the Brewers a year later as part of the Willy Adames trade. Stanek didn’t work out with the Marlins and got non-tendered in 2020. Sánchez is still with Miami and is kinda sorta carving out a role as a platoon bat.

Cubs, then Astros get Martín Maldonado: Say what you want about Maldonado’s bat, but there’s no denying Astros pitchers loved throwing to the guy. He finished 2018 with Houston, signed with the Royals after the season, then Kansas City traded him to the Cubs for lefty Mike Montgomery on July 15, 2019. Two weeks later, the Cubs traded him to the Astros for Tony Kemp. That time the Astros didn’t let him leave as a free agent. Maldonado remained with Houston through the 2023 season.

Astros get Aaron Sanchez: This trade is notable only because Sanchez started a combined no-hitter in his first appearance with Houston. He threw the first six innings and Joe Biagini, another part of this trade, tossed an inning later.

The Astros got Biagini, Sanchez, and minor-league outfielder Cal Stevenson from the Blue Jays for outfielder Derek Fisher. Biagini and Sanchez combined for a 7.65 ERA with Houston. Fisher put up minus-0.5 WAR in parts of two seasons with the Blue Jays.

Teams that needed to do more

Sometimes the best trades are the trades you don’t make, and sometimes the worst mistakes are the trades you don’t make. Here are three teams that had clear needs going into the 2019 deadline, but did not address them.

Dodgers: Los Angeles was a juggernaut in 2019 — 70-39 on deadline day with a 15-game lead in the NL West — though the bullpen was a sore spot, and it was not addressed. The Dodgers make several smaller pickups at the deadline (Jedd Gyorko, Adam Kolarek, Kristopher Negron, Tyler White), then watched their bullpen surrender 14 runs in 18 2/3 innings in the five-game NLDS loss to the Nationals. Clayton Kershaw came out of the bullpen in Game 5 and allowed back-to-back homers to Anthony Rendon and Juan Soto to tie the game. The Dodgers eventually lost when Joe Kelly served up a 10th-inning grand slam to Howie Kendrick. In the decisive Game 5, the bullpen that was not reinforced surrendered six runs in 3 1/3 innings.

Twins: The Twins and Cubs were the only teams in baseball to have five pitchers make at least 26 starts each in 2019, but, going into the deadline, the AL Central-leading Twins needed a starter. José Berríos and Jake Odorizzi formed a solid 1-2 punch, and the staff behind them (Kyle Gibson, Martín Pérez, Michael Pineda) was a bit shaky. Minnesota did not add a starter, won the AL Central anyway, then got swept by the Yankees in the ALDS. Their starters (Berríos, Randy Dobnak, Odorizzi in that order) allowed seven runs in 11 innings in the three ALDS games. Sergio Romo was the club’s big deadline addition.

Yankees: New York imported Edwin Encarnación in a trade with the Mariners on June 15, and that was it. The Yankees sat out the deadline (other than an inconsequential swap of minor-league pitchers with the Rockies) even though they had a need for rotation help. The Yankees advanced to the ALCS and had to start a gassed Chad Green as an opener with their season on the line in Game 6 because their rotation was shorthanded. Like the Dodgers and Twins, the Yankees did eventually win their division in 2019, and also saw their season end earlier than they would have liked because a roster deficiency was not addressed at the trade deadline.