It’s not like the Phillies and Astros don’t have some compelling history. The 1980 NLCS was one for the ages: Mike Schmidt and Steve Carlton versus Nolan Ryan and Joe Morgan, the maximum five games, the last four decided in extras. I rewatched Game Five on DVD a few years ago and got clenched-stomach nervous right up until Garry Maddox squeezed the last out in the bottom of the 10th. 25 years later, the Astros rabbit-punched Charlie Manuel’s first Phillies club en route to their only National League pennant, and for pretty much the rest of the Phils’ mini-dynasty unpleasant things tended to happen when they faced Houston.
But for the most part, the heavy action between the two teams has come in the offseason, as they made no less than seven significant trades from 1992 to 2015. We’ve got descriptions of each below. Note that Wins Above Replacement (WAR) figures are only for the players’ tenures with the Phillies and Astros. Also, this reflects direct trades only—so, for instance, Bobby Abreu doesn’t show up here, since the (Devil) Rays plucked him from Houston’s roster in the 1998 expansion draft just before dealing him to the Phils for Kevin Stocker. And yes, I did just take a gratuitous opportunity to mention the Stocker-for-Abreu trade, because it makes me happy. Always has, always will.
The story: The Phillies took a chance on a young Schilling, joining his fourth organization at age 25, whose talents had not yet outweighed his lifelong recurrent pattern of being an obnoxious pain in the ass. Give then-GM Lee Thomas huge credit, though, because over the next eight and a half seasons, Schilling turned in the greatest sustained performance from a Phillies right-hander over the half century between Robin Roberts and Roy Halladay. Grimsley, meanwhile, never made a big league appearance for Houston, which released him the following spring. He did carve out a decent career as a lefty journeyman, albeit highlighted by this incident.
The score by WAR: Phillies (Schilling) 36.8, Astros (Grimsley) 0
Who won the trade?: Duh.
The story: It wasn’t safe for Mitch Williams in Philadelphia after the 1993 World Series. In a more rational world, people would have understood that manager Jim Fregosi was the guy who sent a thoroughly shot Wild Thing out to kill fans’ dreams in Games Four and Six (and done nothing more than maybe shake their heads disapprovingly when seeing him out buying smokes). But the team couldn’t bring Williams back for the next season, so they made the first of the four closer-centric trades on this list, swapping Mitch for his stylistic opposite in Doug Jones. This is not the former Alabama Democratic Senator Doug Jones, nor the Agent Cooper alternate persona from Twin Peaks: The Return Dougie Jones; this is a guy whose fastball, as they say, could not break wind. Think “right-handed Jamie Moyer with a cool mustache.” Yet he was an all-star on merit in 1994, totaling 27 saves with a 2.17 ERA in that strike-shortened campaign. Sadly, Jones passed away in 2021. Williams, meanwhile, was soon out of baseball. As for Jeff Juden… well, he did have this game.
The score by WAR: Phillies 2.5 (Jones 2.3/Juden 0.2), Astros -0.9 (Williams)
Who won the trade?: The Phillies, by virtue of Jones’s one really good season, but this deal wasn’t really long term impactful.
The story: The Phillies knew they were close in the early 2000s. By the time of this deal, the lineup included Mike Lieberthal, Jim Thome, Bobby Abreu, and Pat Burrell; the rotation boasted Kevin Millwood, Brett Myers, Randy Wolf, and Eric Milton. It was a good team. They’d been undermined in 2003 by a closer performance from Jose Mesa that would set a standard for abject awfulness that stood until… well, one of the guys still coming up on this list. So GM Ed Wade traded for Wagner, a borderline Hall of Fame talent (I’d vote for him) who was great in 2004 and 2005 when available, and when he wasn’t mouthing off about the fans. (One time he decidedly wasn’t great was this game.) Wagner went on to continue pitching well for the Mets and Braves, other than when he threw into Pat Burrell’s swing path. Of the three young pitchers traded to Houston, all wound up delivering sub-replacement level value for the Astros. Prospects, amirite?
The score by WAR: Phillies 3.9 (Wagner), Astros -4.1 (Astacio -1.9, Buchholz -0.9, Duckworth -1.3)
Who won the trade?: The Phillies. Wagner is an all-time great reliever, and while he didn’t stick around long (and then suited up for two bitter rivals), he did his job while here.
The story: The Phillies stormed to a playoff berth in 2007 after enduring a hellstorm of bullpen chaos that ended only when erstwhile Opening Day starter Brett Myers took over the role in midseason. Myers was a good closer, but the team wanted to move him back to the rotation for 2008, so they traded for Lidge. You know the rest: Lidge turned in one of the greatest relief seasons in baseball history—or at least one of the most effective—in 2008, and won a World Series. Then he turned in arguably the worst season we’ve ever seen from a closer in 2009. He actually rebounded to be pretty effective in his last two seasons with the club, and is much loved in Philly to this day. For his part, Bruntlett scored one of the most important runs in Phillies history—the game-winner in 2008 World Series Game Three—and turned an unassisted triple play, against the Mets. Meanwhile, the Astros began their long rebuild under former Phils GM Ed Wade; Bourn, who had nowhere to play in Philly with Pat Burrell, Shane Victorino, and Jayson Werth in front of him, eventually became an all-star. He is the best player the Phillies traded to Houston in any of these deals. How many times over the years have you lamented that Michael Bourn did not reach his career heights in a Phillies uni? That’s what I thought, and same here.
The score by WAR: Phillies 0.6 (Lidge 1.7/Bruntlett -1.1), Astros 12.8; (Bourn 12.0, Geary 0.8, Costanzo n/a)
Who won the trade?: As we all know, WAR flies forever, so I guess Hou—wait a minute, I’m being told that actually flags fly forever. Lidge could have failed to record an out for the rest of his career after that slider Eric Hinske swung over; wouldn’t change how anybody feels about this trade. Call it a win-win, I guess.
The story: The previous December, coming off a six-game loss to the Yankees in the World Series, GM Ruben Amaro Jr. landed his white whale in trading for Toronto Blue Jays ace Roy Halladay. For about a day, the Phillies had a terrifying, intoxicating rotation top three of Halladay, Cliff Lee, and Cole Hamels. Then he traded Lee for… you know what, let’s not get into that. The point is that come the following trade deadline, the Phillies needed another arm, and Amaro dealt a solid package for longtime Astros top dog Roy Oswalt. Although overshadowed by Doc’s transcendence, Oswalt was absolutely electric down the stretch for the 2010 Phils, going 7-1 with a 1.74 ERA. Happ went on to a very good career in his own right, and Villar eventually emerged as a useful guy. Gose began his pro career as a fast outfielder who couldn’t hit; quickly traded to Toronto from Houston, he was a fringe guy until 2016, then converted to pitching. He returned to the majors in 2021 with Cleveland, and made 22 appearances for the Guardians this past season.
The score by WAR: Phillies 5.4 (Oswalt), Astros 1.1 (Gose 0.0, Happ -0.2, Villar 1.3)
Who won the trade?: Phillies. This one isn’t as close as it might seem, because with the marginal exception of Villar, all the guys Houston got did their best work as former Astros.
The story: Amaro’s last all-in deal, on the anniversary of both his Oswalt and (acquiring) Cliff Lee trades. The Phillies weren’t exactly hurting on offense, but they understandably felt one big righty bat short going down the stretch. Pence, one of the more ungainly pro athletes you’ll ever see, turned in an excellent two months that ultimately didn’t matter much, though I suppose without him the team might not have won a franchise record 102 wins. The next summer, Amaro traded him away for a forty-something catching prospect named Tommy Joseph and a couple other guys. (Not really; Joseph was 21. But look at this guy and tell me he’s not middle-aged. I’m middle-aged. I know.) Meanwhile, some fans (looks down in embarrassment) absolutely plotzed over the obscene bounty of talent allegedly surrendered for Pence. Yadda yadda yadda, none of those guys turned out to be all that good, though Santana was a decent power source for a few years in the late 2010s, well after Houston dealt him away.
The score by WAR: Phillies 3.3 (Pence), Astros 2.1 (Cosart 2.9, Santana -0.4, Singleton -0.9, Zeid -0.5)
Who won the trade?: The Phillies, I guess; Pence more or less did what he was supposed to do, while none of the prospects were still around in key roles by the time the Astros got good in the middle of the decade.
The story: Finally, the big name goes from Philly to Houston rather than the other way around. Matt Klentak’s first major move was a reasonable-seeming deal to shop his dynamic, cost-controlled young closer for a package of promising arms. For one bright shining moment in April 2016, it looked like Vinny Velo alone was going to justify this thing. Unfortunately, he never again had a start remotely as good as that 16-strikeout masterpiece. Olberholtzer made the ’16 team as well, and quickly became known as manager Pete Mackanin’s effective white flag. Eshelman, an alleged control maestro, showed the limits of what location could do for you when uncoupled with effective movement or spin. Amazingly, the last man standing from this trade was Mark Appel, the former first overall pick who struggled with the Phillies, retired in 2018, unretired in 2021, and finally made it to the bigs in 2022. Giles was Houston’s primary closer in 2017 when they won* the World Series, though he had a dreadful postseason during which he lost the job, and was traded the following summer. He’s struggled with injuries since then.
The score by WAR: Phillies 4.3 (Velasquez 3.9, Appel 0.3, Olberholtzer 0.1, Eshelman n/a, H. Arauz n/a, Astros 1.6 (Giles 1.6, J. Arauz n/a)
Who won the trade?: I guess you have to give this to the Astros by the same logic the Phillies “won” the Lidge trade. Car-crash gruesome as Giles was in the 2017 playoffs, he helped them get there with a very good regular season. And any evaluation of a transaction that requires you to well-actually the performance of Vince Velasquez feels as shaky as any lead he was charged to protect heading into the middle innings.
|Trade (biggest name)||Phillies||Astros|
|Trade (biggest name)||Phillies||Astros|
The net result of these seven trades is that the Phillies took the value of 44.2 WAR from the Astros. Most of that is Schilling, of course. Then again, pull out Michael Bourn and the guys that went from Philly to Houston had collective negative value!
If somehow you could break the rules of space and time and mash all of this into one cosmic mega-trade (in which Ed Wade would be part-GM of both teams), excluding the guys who never played in the majors for either team, here’s what you’d have:
Phillies get: Curt Schilling, Doug Jones, Jeff Juden, Billy Wagner, Brad Lidge, Eric Bruntlett, Roy Oswalt, Hunter Pence, Vince Velasquez, Mark Appel, Brett Olberholtzer
Astros get: Mitch Williams, Brandon Duckworth, Ezequiel Astacio, Taylor Buchholz, Michael Bourn, Geoff Geary, Jarred Cosart, Jonathan Singleton, Josh Zeid, Domingo Santana, Ken Giles
If you were drafting among these players, there’s no way you’re taking anyone the Astros got sooner than fifth or sixth, depending on how you feel about Lidge vs. Bourn. All these moves made logical sense for both teams at the time. But in the aggregate, the Phillies might have plundered Texas-based resources as completely as any organization this side of Standard Oil.