Will the Astros’ massive trade for Zack Greinke pay off in a World Series?

The Houston Astros didn’t win the World Series on Wednesday, but it certainly felt like they won something.

By being the bravest, boldest and most aggressive team in baseball at the trade deadline, the Astros vaulted themselves into instant championship favoritism and sent some high heat directly at the chins of their main rivals.

As 72 players headed for new homes on an explosive and unexpected final day before the cutoff, Houston landed themselves the best of all those needing to be measured up for new uniforms. Zack Greinke, acquired from the Arizona Diamondbacks in exchange for four prospects, gives the 2017 champions yet another arm from the gods and ensures their postseason roster will have a truly terrifying look.

Greinke will be paired in the rotation with Justin Verlander and Gerrit Cole. Using baseball’s endless mnemonic stat counters, they are either the No. 1, 3 and 5 pitchers in baseball (WHIP) or 1, 3 and 8 (ERA). By any measure, they are a fearsome front-end rotation — and amid the fuss, the Astros also quietly bolstered their bullpen. There will be nowhere to hide.

“We really don’t have any holes right now,” Houston general manager Jeff Luhnow said. “If we stay healthy, this team is as good as any team I’ve ever seen.”

The upside of making seismic moves late in the deadline window is obvious. Make the right one and it can take you all the way to the promised land. The Astros went big in 2017, swooping in during the final seconds of the Aug. 31 playoff roster window to get Verlander. They wound up winning it all, completing a transformation from being the worst team in baseball for years.

In 2016, Aroldis Chapman got the Chicago Cubs over the line, his thunderbolt arm providing the ultimate salve for all that generational franchise anguish. A year earlier, the Kansas City Royals had two deadline acquisitions, Ben Zobrist and Johnny Cueto, to thank for monumental postseason performances that resulted in winning the Series.

For whatever reason, acquired players have come up big time and again on title-bound teams. Travis Ishikawa’s walk-off for the San Francisco Giants in the 2014 NLCS. Jake Peavy’s clutch pitching for the Red Sox in 2013. Hunter Pence’s relentless slugging and all-around positivity during the Giants’ 2012 run.

Why didn’t the Yankees make a big move at the deadline, and can they win the World Series with what they have?@The_ChrisMyers – @Sweendog9 – @jonmorosi pic.twitter.com/02e6LtLowG

— FOX Sports: MLB (@MLBONFOX) August 1, 2019

Yet while often it is a trade that makes all the difference, it is not always the obvious blockbuster. Last year, the Boston Red Sox grabbed Nathan Eovaldi’s arm from Tampa Bay at the deadline, then watched as he did his best Iron Man impersonation down the stretch to overcome a Dodgers team led by deadline acquisition headliner Manny Machado.

Of course, sometimes the biggest deadline moves don’t even pay off. Houston’s big move for Randy Johnson in 1998 generated headlines aplenty, and the Big Unit played superbly. But those Astros didn’t make the World Series, and the pieces sent to the Seattle Mariners in return — Carlos Guillen, Freddy Garcia and John Halama — were outstanding for years in the Pacific Northwest. Eric Gagne was the big prize at the 2007 deadline, and although the Red Sox went on to win the World Series, the reliever was injured and didn’t contribute much to the accomplishment.

Then there is perhaps the greatest cautionary tale of all — started by a trade but cemented by a subsequent free-agent signing — that has morphed into the dread associated with teams flipping prospects for established stars with short-term arcs.

In 2008, the Angels grabbed Mark Teixeira from Atlanta at the deadline, pairing him with Vladimir Guerrero on a team that had the best record in baseball and a World Series in mind. Teixeira performed strongly, but the Angels flamed out in the division series, and the star first baseman then bolted to the Yankees in the offseason.

Back then, if a midseason acquisition left in free agency, a compensatory draft pick was awarded. The Yankees gave up the 25th pick in the 2009 draft to sign Teixeira. The Angels turned that little consolation prize into a kid out of New Jersey by the name of Mike Trout.

Add it all up, and it just goes to show how complicated this whole situation is. The Yankees missed out on Trout, but won the World Series in 2009. The Angels have the best player in baseball as a result of their trade of Teixeira, and they’re still waiting to sniff a ring. Sometimes, things work out when they don’t, and vice-versa — although the reward so often outweighs the risk.

Sure, the returns across the board are mixed. Jalen Beeks, the trade bait for Eovaldi, has been a solid pitcher for the Tampa Bay Rays and shows some promise. The three players traded for Verlander in 2017 have made a combined two major league appearances. The Chapman trade netted the Yankees a prospect who became a two-time all-star in infielder Gleyber Torres.

Alex Bregman knows.

h/t @BenReiter pic.twitter.com/mgviOiofkK

— FOX Sports: MLB (@MLBONFOX) July 31, 2019

Even with those risks, everyone understands the benefits a deadline trade can bring. Not everyone is prepared to pull the trigger, given the possible long-term impact associated with such moves. But when you’re chasing the biggest prize, you have to take the biggest swings. And the Astros did.

“We tried,” Red Sox’ Dave Dombrowski told the Washington Post. “We just didn’t like the asking prices. We went right to the very end.”

We will see how it pans out this time, for Houston and for their biggest competitors. By sitting tight and respectively doing nothing (the 68-39 first-place Yankees) and very little (the 71-39 first-place Dodgers), those mega-market heavyweights guaranteed that they will be lampooned by their fan base if they flame out in the playoffs. Especially if the Astros go on to win a second title in three years.

“You can’t win the AL pennant on July 31,” wrote the New York Post’s Joel Sherman. “But can you lose it?”

The Astros felt they could take the risk. Maybe they felt they couldn’t afford to pass.