Every team in major league baseball has made a multitude of trades over the course of their existence. Some teams, of course, have been around a lot longer than others. That means that some of those older teams have made a bunch more notable trades than most. And to be notable, well, it does not mean they have to be good trades. Some might be, but odds are there’s quite a few stinkers among them. And if we are being fair, we need to cast a wider net. As in, let’s examine all aspects of team building. For example, teams don’t just build through trades. There is the draft and free agency too. And with that in mind, those areas should be fair game too.
So with all that said, some teams have really made some amazing moves, right? Amazingly good, and amazingly bad. And, one of my favorite teams, the Phightin’ Phils, have done this as well. And when you think about it, this all makes sense. They are one of the older baseball franchises, after all. They are one of the few teams in baseball to have lost ten thousand games. Now, you can’t lose that many unless you’ve been around forever, and if you’ve found yourself lacking in talent. And you generally only find yourself lacking talent when you have some major front office issues-bad trades, bad drafting, questionable free agency moves. And, the Phillies have been around so long, some of their biggest blunders folks actually have forgotten about, or may have completely not even realized the Phillies were a part of. Seriously, that’s how long they’ve been around. Some of these guys on the list, you are going to be floored that they were ever on the Philadelphia Phillies roster at all. But, there’s also good news. After all, these guys have also won over 9500 games, and among those, two World Series titles. Which means? Well, there has to have been a few good moves in there too. So let’s take a look at the list!
16 WORST: Trading Away Scott Rolen
Why is this one on here? Because this was a shining example of front office ineptitude, if you ask most fans and other baseball experts. Scott Rolen was, quite honestly, one of the better third basemen in baseball at the time, and he was, hands down, the best third baseman the Phillies had had since a certain first ballot Hall of Famer named Schmidt manned the hot corner. And, here’s the brutal reality of these kinds of trades, in any sport: in almost every instance, when you are trading a huge star, you don’t get similar returns. Mostly, you gamble on a package of prospects, hoping that if you haul in a huge bunch of decent prospects, one or two will actually pan out. The Phillies picked up a few bodies in return, and while Mike Timlin was a decent pickup, the cornerstone of their return was Placido Polanco. And while Polanco was a very good player for the Phillies, he was no Scott Rolen.
15 BEST: Signing Jim Thome
While Thome never led the Phillies to the promised land of a World Series title directly, he indirectly had a hand in it. And, just as important, it was his signing that kind of ushered in that next (and most recent) run of Phillies success. The Phillies signed the big first baseman away from the Cleveland Indians in 2002, just before Christmas. And he had a big impact on the Phillies, bringing some much needed pop to the lineup, and instantly boosting their profile. He had two good years with the team before injuries opened the door for his replacement, Ryan Howard. But Thome wasn’t done being useful for the Phils. Nope, they flipped him to Chicago for a package of players which included Aaron Rowand and Gio Gonzalez. Rowand became a fixture on the 2008 World Series team, while Gonzalez has been a stud pitcher (just not for the Phillies).
14 WORST: Drafting JD Drew
Here is one that Phillies fans wish the team would have never, ever bothered to draft. For one, JD Drew was represented by Scott Boras. And while Boras is and was a great agent (for his clients, primarily), he has been known to drive teams nuts with his demands. And this was absolutely the case with Drew. Boras had declared that JD would not sign for less than ten million bucks. And the Phillies at that time were a bit cheaper than they are now. Not much cheaper, but cheaper. They had no intent to sign an unproven player for that big of a deal, and they wound up wasting the pick on Drew. They knew he wasn’t going to sign for their pittance, but they drafted him second overall anyways. It’s a pick they should have gone in a different direction with, to say the least.
13 BEST: Landing Bobby Abreu
This one, quite honestly, could have landed at number one, it was such a stroke of both luck and genius. In 1997, there was an expansion draft taking place. Abreu was, at the time, an outfielder for the Houston Astros, left unprotected to the draft process. The new team, then known as the Tampa Bay Devil Rays, selected Abreu and then promptly flipped Bobby to the Phillies in exchange for shortstop Kevin Stocker. Stocker was nothing more than a solid, very average shortstop. Abreu? He was an efficient offensive player if ever there was one. Phillies fans might have, at times, under-appreciated him, but most baseball men saw his stat lines and drooled. He was very good in a number of offensive categories, and was so for a number of years.
12 WORST: Trading Away Cliff Lee
Remember in the above JD Drew segment when I categorized the Phillies as often cheap? Here’s a perfect example of it. Christmas came early in 2009 for the Philadelphia area, as the Phillies hauled in Doc Halladay (more on this later). The Phillies already had a pretty solid pitching staff, featuring Cliff Lee and Cole Hamels, among others. But the front office decided that Lee and Halladay would be too expensive to keep, while Hamels was coming up on his big payday. Lee was approaching free agency, so he was going to break the bank again too. So, rather than biting the bullet and enjoying what a loaded pitching staff could do for a year, the Phillies opted to quickly turn around and trade Cliff Lee to Seattle for basically nothing good. None of the prospects shipped to the Phillies in the deal amounted to anything.
11 BEST: Acquiring Curt Schilling
Schilling is a great example of a minor league guy who scouts got wrong. I say this because he didn’t come up through just one organization. No, he came up through several before landing in Philadelphia and really announcing his presence with authority. He was originally with the Boston Red Sox, but they flipped him to Baltimore, who then flipped him to Houston. And once in Houston, he finally made his way to Philadelphia, with the Astros receiving Jason Grimsley in return. Needless to say, this one was a trade the Phillies won handily. And while Schilling did go on to enjoy more success with the Arizona Diamondbacks (one World Series ring) and Boston (two rings), he established himself as a dominant star in Philadelphia. He was a strikeout artist, recording over 3,000 in his career, and an absolutely dominant post-season ace. It should only be a matter of time before he lands in Cooperstown.
10 WORST: Trading Gio Gonzalez And Gavin Floyd For Freddy Garcia
Yes, I assure you, that trade actually happened. It was most regrettable pretty much right from the beginning, yet someone in the front office ACTUALLY thought that Garcia was worth the move. The Phillies had actually previously acquired Gonzalez from the White Sox, along with Aaron Rowand, for first basemen Jim Thome. Then, a year later, they decided to flip Gonzalez and Floyd for veteran Freddy Garcia. Now, Garcia had a decent career, but he basically was done when the Phillies picked him up. And following that trade? Gonzalez has been a star pitcher, and while Floyd never quite reached Gio’s level, he has had himself a very respectable career in his own right. It was instantly regrettable, and if fans had the ability to veto trades, this one would have been killed off in a blink.
9 BEST: Assembling The Core Of The 2008 Team
Fine, I am lumping a few guys into one spot, but I have a reason. I didn’t think any of them, however, warranted their own individual section, so we might as well just do a collective one here. And who are those guys? How about the biggest names-Ryan Howard, Chase Utley, Jimmy Rollins and Cole Hamels. To a lesser extent (but, honestly, oh so barely a lesser extent), you could also add in Carlos Ruiz, too. And why not factor in Pat Burrell, too? And do you know why these guys, six that I named, are so special? Because none of these guys were traded for, nor were they big money free agent signees. Instead, every one of the names I just rattled off was a homegrown talent, so to say. Every single one of those men were drafted by the Phillies organization, which speaks to the success of the front office (scouting and general manager) during that time and the time before it too, considering how long a draft pick takes to mature at times). This was as impressive a group of homegrown talent as the Phillies might ever assemble.
8 WORST: Trading Away Grover Cleveland Alexander
Pay attention folks, this is going to start showing a trend soon enough. Just wait…
Now, Grover Cleveland Alexander was an excellent pitcher for the Phillies. He cranked out a number of thirty-plus win seasons, which in 2017 would be like, an eighteen-win season or something. He was really an extremely good pitcher, one of the best in his generation. And if you know when Alexander was a hurler, you’d know two things. First, there were some really good pitchers back then, such as Walter Johnson. Second, he was in his prime right as World War I broke out. As such, the Philadelphia Phillies expected to lose years of Alexander’s career to one of the Armed Services. Rather than see that happen, the Phillies traded Alexander (and another player) to the Chicago Cubs, for a player named Pickles and some other forgettable people. While Alexander did indeed serve during the War, he also did still end up being a good postwar pitcher for both the Cubs and Cardinals. Lesson learned? Never trade an ace for Pickles.
7 BEST: Bringing In Cliff Lee
This one was an all-in move that wasn’t as good as many fans had hoped, but hot off of their 2008 World Series win, the city, the fans and the team were compelled to do whatever they could do in order to bring in a second championship in as many years. And, to do that, the Phillies front office decided to ship a package of prospects off to Cleveland to reel in the crown jewel of that year’s deadline prizes. No, the Phillies did send a few decent enough prospects back — Carlos Carrasco has had some good years, and Knapp showed promise, but didn’t amount to much. The Phillies easily won this trade, and while Lee didn’t help them to a second consecutive title, he did at least help them reach the World Series in back to back years. However, when another ace was brought in, Cliff found himself being traded yet again. Don’t sweat it, Phils fans. He was signed back by the team in free agency.
6 WORST: Trading Curt Schilling For Travis Lee et al.
This one is more recent, but it still stings oh-so-much. Curt Schilling was one of the more dominant pitchers of his era, a strikeout artist who was just a flamethrower. But after the Phillies' improbable 1993 World Series trip, the luck had run out and just about everyone was able to see that trading Schilling was one option in order to improve the rest of the club and return to a more competitive position. The theory was sound, and plenty of teams have done similarly. The problem is trading a star pitcher for a package of talent is a risky proposition. Sometimes the talent busts, sometimes they don’t. In the case of the Phillies, they got some middling returns at best. Travis Lee was about as average as you could get, showing hints of what could have been. Omar Daal was the epitome of mediocre for the most part. Nelson Figueroa never amounted to anything. Vicente Padilla was the lone bright spot, but even he had some hits and misses. Meanwhile, Schilling, if you can believe it, actually improved, while winning a couple World Series titles in Arizona and Boston.
5 BEST: When Doc Hallady Rides Into Town
Roy Halladay was, quite honestly, the biggest name being discussed during the offseason in 2009. And, as they had done with the Cliff Lee deal, the Phillies went out and got him. It cost them a couple decent prospects, one of whom is still enjoying a solid major league career (Travis D’Arnaud), but Halladay was electric in Philadelphia. He tossed a perfect game, the twentieth in Major League history. And as if that wasn’t awesome enough, he tossed only the second no-hitter in Major League playoff history in the same year. Unfortunately, Halladay and the Phillies were not getting back to the World Series. Eventually, Halladay began to break down as all players do, and fans were left wondering “what if”. But, we at least got to enjoy him while we could.
4 WORST: Trading Away Ferguson Jenkins
Really. The Phillies actually had this Hall of Famer on their staff at one point. The team signed him to a minor league contract in 1962, and he worked his way up to the big club, where he found work as a young reliever in Philadelphia. His start in the City of Brotherly Love was unremarkable. Based on early returns, you would not have assumed he was going to amount to much, and clearly the Phillies were short-sighted too. They decided to flip Jenkins to the Chicago Cubs in a multi-player deal, where the Phillies, for all intents and purposes, got bupkis back. OK, so that isn’t entirely true. One of the guys they got back set a record for worst season of batting in Major League history, so there’s that. As for Jenkins? He only rattled off a long streak of 20 win seasons and punched his ticket to the Hall of Fame. Salt in an open wound? How about imaging a Phillies rotation of Jenkins and Carlton? Sorry, fellow Phils fans.
3 BEST: Picking Up Mike Schmidt
This one has to be one of the easier top transactions in any team’s history. Simply put, Michael Jack Schmidt was the face of the franchise for an extended period of time. He was the heart of the team that won the city their first of only two World Series titles back in 1980. He’s a member of the 500 home run club, and arguably the best third baseman to ever man the hot corner. That bit is certainly one that many would debate, but if you chose to position Schmidt as the best ever at his position, you’d not be beaten up over it. And the funny thing was (and I say this as a Philly fan who grew up during Schmidt’s prime), there were plenty of fans who weren’t exactly fond of him at times during his playing days. Perhaps they had hoped his greatness would elevate the team more, and bring in more titles? But it didn’t, and that’s life. Now far removed from his playing days, he is easily one of the most beloved Phillies of all time. If you want to make him number one, I’d be totally fine with that. I think the top two are really more like a 1A and 1B, to be quite honest. And all of that greatness, in Schmidt’s case? Acquired as an undrafted signee. How do you like that for good scouting?
2 WORST: Trading Ryne Sandberg Away
Now, I know there are fans that might look at this one as not so bad, because Sandberg, while a Hall of Famer, did not lead the Cubs to a playoff win, or even the World Series. The Phillies, after dealing Ryne? They had some post season success at least. If that is your measuring stick, so be it. With that said, however, it still has to land here. Yes, the Phillies at least got better in return than prior trades with the Cubs (seriously, why were the Cubs always getting the better of the Phillies in trades?), but you can’t overlook the fact that, after being dealt away, Ryne Sandberg only happened to have a Hall of Fame career, becoming one of the best second basemen to ever play the game. The Phillies did bring him back as a manager more recently, but that tenure was an utter failure.
1 BEST: Bringing Lefty To Philly
Many superstars have a nickname. Some are plays on their names, like A-Rod. Others are not, but when you hear the nickname, you know full well who people are discussing. Such is the case with Lefty, otherwise known as Steve Carlton, who is quite simply, one of the best pitchers of his, or any other, generation. The Phillies basically stole him from the St. Louis Cardinals in 1972, sending Rick Wise to the Cardinals in return. And what did Lefty do upon arriving in Philadelphia? He basically made them instantly more respectable. They made it to the post-season more frequently than ever. He won the Cy Young four times, made numerous All-Star teams and, after being the second pitcher to eclipse baseball’s all-time strikeout record, he and Nolan Ryan would trade ownership of it for years until Carlton retired. Considering what he did after the trade, this was easily one of the most lopsided trades in history.