Because Schilling was moved multiple times before he began to pile up accolades, he holds another singular distinction. Schilling is the only player involved in more than one of the 15 most lopsided trades in AL/NL history, as measured by the future WAR produced by players on both sides—and he was involved in three. The table below lists those 15 trades, with the ones featuring Schilling ranking first, fourth, and 15th.

I haaaaate when trades are evaluated in this way, ignoring contract lengths and such. The 15th in the list is Schilling for Jason Grimsley, in which Philadelphia is listed as gaining 79.3 WAR in the transaction. In reality the Phillies gained 12 WAR in that transaction, as they acquired the rights to Schilling only through the 1995 season. The rest of his WAR after 1995 was gained in subsequent free agent contracts or lost via trade, which are separate transactions. Same for the Schilling/Anderson for Boddicker trade: the former players produced 22 WAR before free agency, and Boddicker produced 11 in the remainder of his contract. The real difference is about one-ninth what Lindbergh says it is.

Like, Oakland didn't acquire 14 WAR worth of Jon Lester in 2014, and they didn't trade 13 WAR of Yoenis Cespedes to get him. It was more like gain 3, give 8, given the remaining contracts. Looking at it the former way makes it seem like it was a balanced trade slightly in Oakland's favor. It definitely wasn't, at least from a WAR perspective. It was in their favor in the sense that they got what they needed for the stretch run to make the WC game. But they gave up a lot to get what they did.

I mean, the Astros still lost the Schilling trade; I'm not suggesting they didn't. But it's certainly not one of the 15 most lopsided trades in AL/NL history.

Roids, obviously.

VI, your way of analyzing trades is obviously correct if you're running a FO. But when you're looking historically, looking at it that way all of the lopsided trades will be from the pre-FA era. The shorter your control of the player, the less you have to win or lose by trading them. The only modern trades that will even come close are prospect-for-veteran trades, but they will by default always look lopsided unless the prospect is a total flop. I'm not sure how to make a list like this - maybe just divide by era?

I think Schilling was traded so often as a young guy for the same reason he's not making the Hall: he was a total headcase with an untreated personality disorder.

I think Schilling was traded so often as a young guy for the same reason he's not making the Hall: he was a total headcase with an untreated personality disorder.

Seems the article goes to great lengths to dispel this idea, as the trading teams talk about his potential and his immaturity/average work ethic overall, but point out that he was seen as a good teammate/clubhouse guy, etc.

Roids, obviously.

You're probably kidding, but Schilling saw a much greater spike in his value after the age of 30 than, say, Roger Clemens ever did. His best seasons by WAR come at 34, 35 and 37.

The best four-year stretch of his career by far began with his age 34 season, which also coincides with him joining Luis Gonzalez' team. Make of that what you will.

I was (kinda) kidding, but those Phillies teams were not short of users either.

I was (kinda) kidding, but those Phillies teams were not short of users either.

Given how much those guys seemed to hate him, I'm not sure any of them were willing to share their stashes.

Schilling and Dykstra really should have been best friends.

I was (kinda) kidding, but those Phillies teams were not short of users either.

Dykstra, Daulton...who else? Pat Combs? Braulio Castillo?

Unplugged Lenny was pretty awesome in Once Upon a Time in Queens.

You're probably kidding, but Schilling saw a much greater spike in his value after the age of 30 than, say, Roger Clemens ever did.

Ironically it was Clemens who lectured Schilling about weight training among other things that Schilling says turned his career around.

I was (kinda) kidding, but those Phillies teams were not short of users either.

Dykstra, Daulton...who else? Pat Combs? Braulio Castillo?

Danny Jackson was pretty pumped.

I've done this before ... just interesting, especially since the years and ages perfectly overlap, and it was relevant in that year they shared the ballot ... Schilling vs Smoltz by age:

CS 21-24: 145 IP, 88 ERA+, 0.2 WAR
JS 21-24: 733 IP, 103 ERA+, 12.4 WAR

Not even close

CS 25-32: 1547 IP, 127 ERA+, 34 WAR
JS 25-32: 1681 IP, 131 ERA+, 31 WAR

Close. Schilling's WAR edge is due to a worse defense, Smoltz with the small IP edge. Largely a coin flip.

CS 33: 210 IP, 134 ERA+, 5 WAR
JS 33: hurt

CS 34-37: 911 IP, 150 ERA+, 31 WAR
JS 34-37: 285 IP, 162 ERA+, 7 WAR

The closer years, obviously Schilling in a landslide here. Schilling's numbers were ... not literally incredible but his RA9 went down substantially despite pitching in big hitters parks in front of below-average defenses. As much WAR in 4 years as in the 7 years of his "prime." On the other hand, it was still true that his home ERA was a good bit higher than his road ERA in those years so the parks had the expected effect.

CS 38+: 448 IP, 110 ERA+, 10 WAR
JS 38+: 773 IP, 124 ERA+, 16 WAR

So for the years when both were healthy and primarily starters, Smoltz had a healthy 59-44 WAR edge and about 1,000 more innings. During Smoltz's injury-affected years not only did Schilling obviously dominate in both IP and WAR due to being a SP but Schilling also hit his peak. Whether Smoltz really needed to spend 4 years as a closer (he was excellent) we'll never know and, of course, no reason to think Smoltz would have matched Schilling's peak.

Two careeers that are about as parallel as you get and, based on 15 of those 20 seasons, you'd take Smoltz, especially with that IP edge. Those other 5 seasons push Schilling out to a big career WAR edge while I suspect that Smoltz was actually the better pitcher in the absolute sense.

Dykstra, Daulton...who else? Pat Combs? Braulio Castillo?

pete incaviglia and dave hollins are additional suspects.

Seems the article goes to great lengths to dispel this idea, as the trading teams talk about his potential and his immaturity/average work ethic overall, but point out that he was seen as a good teammate/clubhouse guy, etc.

consider the source, but...eh...

VI, your way of analyzing trades is obviously correct if you're running a FO. But when you're looking historically, looking at it that way all of the lopsided trades will be from the pre-FA era.

Then just restrict it to the FA era. I'm still sure none of the Schilling trades, properly valued, are in the top 15 most lopsided trades in the FA era. Like, I can come up with three trades by Boston alone that beat any of the Schilling ones.

Seattle got 0.4 WAR out of the remainder of Heathcliff Slocumb's contract, and gave up 27 WAR in the team-control years of Derek Lowe and Jason Varitek.

Houston got 35 WAR in the team-control years of Jeff Bagwell, and gave up 1 WAR of Larry Anderson.

Boston got 17 WAR in the remaining contract years of Josh Beckett and Mike Lowell, in return for 39 WAR in the team-control years of Hanley Ramirez, Anibal Sanchez, and others.

Pick a team, you can find something better (or worse) than a 12 WAR difference. I'm sure you can. Dodgers? Got 3 WAR of Delino DeShields, and gave to Montreal 27 WAR of Pedro Martinez. Braves? 4.6 of Doyle Alexander for 19.2 of John Smoltz. See? I've already named five and I'm barely trying. Lindbergh had Schilling trades in 2 of the top 5 spots all time. They're not even in the top 5 of the free agent era.

(To be fair, searching contract terms and summing WAR takes effort. But, like, I didn't have to do that to name a bunch of more lopsided trades.)

#14

I find this to be an extremely tortured route to try to come to a conclusion that doesn't really have a lot of merit. Before I counterpoint, let me say I would definitely NOT watch his induction speech if he ever gets in. But just talking about on field:

Let's simplify it a couple of ways

First, through age 33 for both pitchers. Before Schilling "peaked". Smoltz has a 512 IP advantage, but they have the same total of WAA and Smoltz only has 4 more WAR despite all the extra innings. They have essentially the same run prevention stats. The RA-9 Is the same despite playing against tougher lineups, in front of inferior defense.
ERA+, ERA, FIP, all a push.. Schilling has 22 more complete games despite starting 112 fewer times !

There is a very slight edge here for Smoltz perhaps due to volume, but it's actually quite small. And Schilling hasn't hit his peak yet.






And then from age 34 to end of career Schilling blows Smoltz completely out of the water. More than twice as much WAA and nearly twice as much WAR








And then of course you have the tried but true method of simply lining up their best seasons top to bottom. Schilling has 11 seasons where he had more WAR than Smoltz. Schillings best 11 seasons total 69 WAR to Smoltz just 52 for his best 11.

Schilling had 15 seasons with higher WAR than Smoltz.

Seems the article goes to great lengths to dispel this idea, as the trading teams talk about his potential and his immaturity/average work ethic overall, but point out that he was seen as a good teammate/clubhouse guy, etc.

Perhaps, but that's not what people said years ago, much closer to the actual facts. When he was a star in Phoenix, people who'd been with the Orioles were pretty open about the fact that they'd dumped him because of his "immaturity," which is usually code for a nutjob of one variety or another.

On the Schilling vs Smoltz argument:

1) It always struck me as an odd conclusion for Atlanta to reach that the best way to handle Smoltz for the four years he was a closer. He was excellent in the role, and it cemented the narrative that he was one of the few pitchers ever to be a great starter and closer. It's probably why he was a first-ballot guy, but it is a little silly. I mean, there are many, many starting pitchers who were nothing near as good as Smoltz who (if put in the role) would have been outstanding short-inning relievers. Also (and I'm not blaming Smoltz for this) this was not the best use of Smoltz for the Braves. There is no way letting him pitch only about 1/4 to 1/3 of the innings he otherwise would have pitched is the best thing for the team, especially when he ended going back to being a workhorse after those four years.

2) If the Hall of Fame and/or the members of the Today's Game committee are worried about Schilling making a maelstrom out of his induction speech, blowing up the spirit of the day, etc., then everybody should just elect all of the controversial - but obviously great - players at once and be done with it. There are 16 members of the committee, and they can each vote for up to four people, meaning there are 64 votes available. Players have to get at least 12 votes to make it. If everybody has their #### together, you could elect five guys at once. So imagine that in 2023 - when it is very possible the BWWAA elects nobody (maybe Rolen, but probably not). Today's Game could elect Bonds, Clemens, Schilling, McGwire, Sosa...just get it all done. Would it be potentially ugly? I suppose, but it would be all done by Labor Day 2023 - nobody would ever argue about it again. Also, I think the attendance for that weekend would be incredible. The people who would be outraged about it would likely stay home, but think about the fan bases who still "their guys": Sand Francisco, Boston, St. Louis, Chicago, some Yankee fans, some Astros fans...it would be a zoo. Then, in 2024, you get Beltre, Rolen, and Helton, and we're back to "normal".

It always struck me as an odd conclusion for Atlanta to reach that the best way to handle Smoltz for the four years he was a closer.

It was initially done to lessen the workload on his arm after his Tommy John surgery. He was so successful in the role that the Braves decided to keep him there. Looking back, yeah, he probably should have been moved back to starter sooner. But it's tough to move a player off a role they are dominating even if it's not as technically valuable to the team.

Smoltz did have the chance to go to the Yankees to start after his first year of closing, but he turned down more money to stay and close with the Braves.

In terms of Schilling, as a lifelong Red Sox fan, it was commonly said right after the 2004 World Series title that a number of people associated with that dramatic breaking of "The Curse" would forever be held as icons in New England. It has now been more than 17 years since that title. Perhaps because the team has won three more since then, and a generation of Red Sox fans are growing up without any of the baggage those before them did, it is difficult for younger fans to appreciate how intense emotions were in the lead up to 2004. But very few of the people who made 2004 happen are held in that rarified place, 17 years later:

Curt Schilling - the bloody sock game was mind-blowingly dramatic at the time, but his words since he retired have made it difficult to talk about him in reverence anymore.
Terry Francona - Still loved around here, but he has been with Cleveland so long that I'm not sure people see him as a Red Sox manager first anymore.
Theo Epstein - Still loved, but doing the same thing for the Cubs has redefined his legacy (enhanced it, right?). He is a local guy - a kid from Newton, MA - and I think many fans still wonder how it ever came to past that Theo and the ownership team couldn't keep it going together.
Manny Ramirez - I think Red Sox fans still love him, and he is one of the greatest right-handed hitters ever - a true savant at the plate. But the PED violations are killing his legacy.
Pedro Martinez - He is treated like Larry Bird, Bobby Orr, and Tom Brady - and yet, his legacy is that he was the guy who bridged the franchise from not a serious franchise in the 1990s to a level of intensity and aspiration I had not experienced in my lifetime. By 2004, he wasn't quite "The Man" anymore, but without 1997-2003 Pedro, we don't get to the mountaintop in 2004.
David Ortiz - Along with Pedro, it turns out that Ortiz is the guy who 50 years from now kids will learn about when the greatest era in the team's history is told. His performance, the postseason success, the leadership, the personality, the smile, his size and attitude - he ends up (along with Pedro, for different reasons) being the guy from the 2004 team that will get the bronze statue, will never have to pay for a drink again...he won.

In December of 2004, I might have said that Schilling would be the guy who eventually "won" the legacy thing from that historic team - he was such a boss that year, and the bloody sock game was amazing - but he blew it, big time.

Adding to #22, one other thing that happened around the same time is that an even more hapless pro team turned into a sport-definiting juggernaut (Patriots). And that team had a single recognizable face (Brady) who is also the generally accepted GOAT in the sport. Maybe it's different for locals, but from a few hundred miles away, the Patriots have just smothered the Red Sox out of the national conciousness with their greater narrative.

Pedro Martinez - He is treated like Larry Bird, Bobby Orr, and Tom Brady - and yet, his legacy is that he was the guy who bridged the franchise from not a serious franchise in the 1990s to a level of intensity and aspiration I had not experienced in my lifetime. By 2004, he wasn't quite "The Man" anymore, but without 1997-2003 Pedro, we don't get to the mountaintop in 2004.

It is a little odd, and perhaps a bit sad (though not very), that the Red Sox' coronation coincided pretty much exactly with the moment when Pedro ceased to be the most magical pitcher in the history of the game and simply became a good one -- his version of a decline, I suppose. In my mind, he's still the face of that team, I guess because he sometimes seemed to be single-handedly dragging them deeper and deeper into the playoffs from 99-03. His relief heroics against the Indians in 99, without a fully healthy body or his best stuff -- it seems like that should have happened in 04, because it was so amazing.

"I just said, 'Hey, if we're gonna be in pain, then we're all gonna be in pain.'" -- Pedro, on that outing against the Indians.

It is a little odd, and perhaps a bit sad (though not very), that the Red Sox' coronation coincided pretty much exactly with the moment when Pedro ceased to be the most magical pitcher in the history of the game and simply became a good one -- his version of a decline, I suppose.

This doesn't contradict what you're saying really, but I was surprised to see that in his first season with the Mets, Pedro was worth 7 bWAR. Not peak Pedro by any stretch, but still Cy Young territory. Then he was done as an effective pitcher.

#18 .... or, as I presented it, Smoltz was clearly better at the beginning and end of their careers; they were basically the same in what are normally the peak years; Schilling blows Smoltz out of the water during the years Schilling started and Smoltz closed (and the year he missed of course) which is exactly what we'd expect because of the difference in the roles but it's far from clear that Schilling was actually a better pitcher than Smoltz in those seasons. Now those 4 seasons also happened to be Schilling's peak so it's unlikely that Smoltz would have matched him anyway even if returning to starting would have been the right move (we'll never know). Given #6 had raised the issue of how unusual Schilling's age 34-37 peak was ...

The WAR/WAA differences in those years are all about the defense which we know is a crude aggregate measure of team defensive quality -- you've got to do something, it's as good as anything else we've got, it's probably accurate enough in this case (I think you'd find widespread agreement those Braves teams were good defensively). It still mostly comes down to whether you'd rather have the extra 15-20 innings a year or you prefer the guy who misses more starts but goes deeper into games and saves you an extra couple of runs per season.

The injury for Smoltz is a clear dividing point in his career although, unusually, it splits his career into 3 bits. The young Schilling taking longer to establish himself means that, in comparison with Smoltz, we get a 4th bit. Smoltz was better in bits 1 and 4, they were equal in bit 2, Schilling cruises in bit 3 when they were in different roles (about half due to being in different roles, about half due to Schilling's peak). But that's "value" and, as I said, I suspect that Smoltz was the _better_ pitcher. There's no question who's more valuable because of those 5 seasons when Schilling was at his peak and Smoltz threw only 285 innings.

We of course have no idea what Smoltz would have done if he'd never gotten hurt. He's credited with 7 bWAR in those years. But for ages 38-40, he came back as a 5-WAR pitcher. On the other hand, prior to the injury, he'd been more of a 4-4.5 WAR pitcher. In the alternate universe where Smoltz never gets hurt, he might have put up 20-25 WAR in those years and that extra WAR would move him into a virtual tie with Schilling in WAR. It is of course possible that Smoltz's arm would have disintegrated if he'd kept starting and we wouldn't even be having this conversation. (FWIW, I thought the move to the pen made sense to save his arm. His return to starting so successfully suggests it wasn't necessary to save his arm.)

It's of course one thing to have these "what if" flights of fancy for, say, Rivera or "what if Gary Nolan hadn't blown out his arm" but it's different for Smoltz because he actually returned to the role and pitched extremely well at ages that even great starters struggle. He was at this level through 32, he was at this level for 38-40, it's a lot easier to have a wonder about "what would he have been like from 33-37?" For example, I don't think I have ever speculated about what would Eck have been like if he'd stayed a starter. We at least have a few data points from Smoltz at that end.

This doesn't contradict what you're saying really, but I was surprised to see that in his first season with the Mets, Pedro was worth 7 bWAR. Not peak Pedro by any stretch, but still Cy Young territory.

Yeah, there are guys in the Hall who never had a season that good. And they deserve to be there, most of them. Just an illustration of how great he was when he was PEDRO.

Pedro ... the most magical pitcher in the history of the game

wait, what?

PEDRO ... THE MOST MAGICAL PITCHER IN THE HISTORY OF THE GAME

wait, what?

It ain't hard. Pedro at his best was a wizard, an artist, and unmatched. Was he the greatest pitcher of all time? No. But was watching a little skinny guy dazzle and terrify the giants of the steroid era the most amazing thing in the history of the game? Maybe you don't agree, but it seems that way to me.

Living in JP at the end of the twentieth century I’d see #45 around, like, painted on the hood of cars, stuff like that. As a Yankee fan, I would flinch, bad magic! I agree with 30-31.

Of course the number has worse associations now….

The Smoltz/Schilling comparison is also interesting because they were both such great and prolific postseason performers:

Smoltz: 15-4, 2.67 ERA in 209.0 IP (also 4 saves)
Schilling: 11-2, 2.33 ERA in 133.1 IP

In the 2015 Hall of Merit election, Schilling, Smoltz, and Mike Mussina were all simultaneously on the ballot. Randy Johnson and Pedro Martinez were the near-unanimous #1 and #2. The columns indicate 3rd, 4th, 5th, and 6th-15th place votes. There were 34 ballots cast.

Schilling: 22 7 1 3 (left off by one voter for being a [deleted] even then)
Mussina: 3 19 5 7
Smoltz: 3 3 17 11

I had them ranked in the consensus order, reasoning that Schilling had the highest peak of the three and Mussina deserved a bonus for pitching his whole career in baseball's toughest division at the time, the AL East.

Schilling was elected. Mussina and Smoltz had to wait a year (2015 was an elect-3 year); both of them sailed in alongside Ken Griffey Jr. and Gary Sheffield.

Around the 2000-2001 time frame ESPN did a poll of MLB hitters as to what was the absolutely nastiest, most knee buckling pitch to hit. There was a tie for the most votes for one pitch between Mariano's cutter and Trevor's changeup. Neither Randy Johnson's fastball nor slider (which, quite frankly, he often used as a sort of changeup) received the most votes, but he received enough votes for each that he had the most total votes overall. The truly remarkable thing, though, was that Pedro was the only pitcher to have 3 separate pitches get votes - his slider, his fastball and his change. That's just insane - That one pitcher could have both a blazing fastball and a great changeup at the same time is just nuts.

I also agree with #30, #31, and #32: Nobody is arguing that Pedro was the greatest pitcher of all time, but what pitcher (maybe, what player) in the last 50 years has been as captivating (or magical) at his peak?

- For several years, when batters were putting up video game numbers, Pedro was the one guy putting up video game numbers...as a pitcher! His numbers are insane - but once you put the offensive context of when he was doing it, it is even more improbable.

- As somebody who lived in Boston during Peak Pedro, I think it is difficult to describe what it was like in the late 1990s and early 2000s in Boston (and New England, really) as it related to the Red Sox. It was like a balloon that was going to burst, in terms of the energy, desire to finally win a championship, the day-to-day intensity of every game, etc. And when Pedro was pitching, it was the ultimate appointment watching. The bars would be full. Friends would schedule dates with their significant others around Pedro starts. We knew in real time that we were living through a once-in-a-lifetime experience. When the Patriots won their first Super Bowl (and even their second one, two years later), I'm not sure we all realized that we were at the beginning of the greatest run in NFL history, with the greatest player and coach in NFL history. But Pedro? We all knew we were a part of something we would never see again. I don't know exactly what to call that realization, but it was magical.

- The style and charisma of Pedro was unreal. Randy Johnson and Greg Maddux were amazing - but nobody would call them charismatic. Pedro Martinez kept improving his English over the years, which allowed those of us who didn't know Spanish to fully appreciate how intelligent and articulate he was (is). He is extremely intelligent, and had a high emotional IQ, as well. You know how when Mike Trout comes up, you don't want to go the fridge or the restroom and miss his AB? Well, with Pedro, the only time you got up was when the REd Sox came up to bat. Nolan Ryan is the only other pitcher who ever was like that in my lifetime - and that wasn't charisma as much as it was that you didn't want to miss another no-hitter.

- The Dominican element shouldn't be undersold, either. He connected the Dominican community in greater Boston to those of us who were from other backgrounds (I am the child of immigrants, but not Dominican), and genuinely made it easy to have conversations, handshakes and hugs, and share a smile together. The energy the Dominican community brought to Fenway Park was a new, exciting, positive energy that lifted everybody up. To be at a Pedro start at the peak of his powers was like being at a high-stakes soccer match in Europe or South America. Baseball doesn't lend itself to that kind of energy very often - but every 5th day for several years, it was like that for three straight hours. It was a gift from Pedro to the fans.

Anyway, one of the highlights of my sports fan life was cheering on Pedro in Cooperstown five years after he retired. It was joyous (talk about energy from the proud Dominican contingent!), it was emotional, it made me so grateful to live in exactly the right place, at exactly the right time, as a lifetime New Englander and sports fan. Can't wait to thank David Ortiz the same way this summer!