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June 14, 2017

The Return of RAJ: Amaro's five worst moves as Phillies GM

If tapped with the task of identifying the most unpopular sports figures in Philadelphia over there last half decade – when none of the four major pro sports teams has flirted with any kind of real success – you’ll think about Chip Kelly, Paul Holmgren, and, depending on your leaning toward the Process, Sam Hinkie, too.

But it’s difficult to imagine anyone more vilified than former Phillies general manager Ruben Amaro Jr. 

Perhaps it’s because expectations for the Phils under Amaro were much higher compared to his peers with the other three teams; Amaro was promoted to the job less than a week after the team won a World Series.

Amaro, a Philadelphia native, former Phillies player, and the son of one of the more influential people in the Phillies organization over the last 50 years, returns to Citizens Bank Park tonight with the Boston Red Sox. He's Boston's first base coach. It’s the first time he’s returning to the ballpark since his seven-year run as Phils’ general manager ended in September of 2015.

Prior to his dismissal, Amaro did lay the groundwork for the team’s current rebuild, in both good moves and bad, of course. He’s more well-known in these parts for the bad. (We’ll look at the good though, too, in the next 24 hours).

But let’s revisit the bad, shall we? (And, we should note, while Amaro was the vice president and general manager, he was hardly alone in signing off on the following deals).

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5. Phillies sign free agent Delmon Young – Jan. 22, 2013

Less than a month before spring training began four years ago, Amaro found his everyday right fielder in Young, a former No.1 overall pick. Young was … fairly young at the tender age of 27, but he kind of fit the baseball scouting definition of “bad body” and was pretty much a designated hitter. (And the second DH Amaro, a GM of a National League team, had added in as many offseason after signing Jim Thome a year earlier.

But back to Young. He wasn’t just a designated hitter, but a designated hitter with poor on-base skills. The not-so-nimble Young had a .299 OBP in his previous two seasons with the Twins and Tigers. So, yeah, he pretty much fit right in with the mess of corner outfielders the Phillies have given significant playing time to in a constant (and still on-going) search for the replacements of Jayson Werth and Raul Ibanez ... who haven’t been around for some time.

How much the Phillies paid Young is insignificant. What’s significant is Amaro and Co. thought he was an upgrade or a solution to the team’s sagging offense. Instead Young was exactly what we all thought he was: he slashed .261/.302/397 in 80 games.

And then there was this: giving a roster spot to Young meant not giving an opportunity to a kid named Ender Inciarte, a 22-year-old Rule 5 pick who was pretty much the polar opposite of Young: athletic. Inciarte, the NL Gold Glove-winning center fielder last season, is now with the Phils division rivals in Atlanta, where he’s hitting .300 with a .353 OBP this year.

Young, meanwhile, was cut loose by the Phillies in August of 2013 … four months after the team offered Inciarte back to Arizona (the D-backs accepted). Here, in chronological order, is how that very roster spot played out from Opening Day to September of 2013: Inciarte–Ezequiel Carrera–Young–Casper Wells. The latter three players combined to hit .236 with a -1.8 WAR for the Phillies in the 2013 season.

RELATED: Amaro looks back on time with Phillies, career change

4. Phillies sign free agent Jonathan Papelbon – Nov. 14, 2011

This is probably a controversial pick since there’s no denying Papelbon’s productivity in his 3 1/2 years with the Phillies. He saved a franchise-record 123 games, sported a 2.31 ERA and 1.02 WHIP, and represented the team in two All-Star Games.

And he was signed less than a month after the team completed a season in which they won a franchise-record 102 games, buoyed by a historically excellent starting rotation. So you can understand why Amaro would want a proven closer for his proven pitchers.

But paying a reliever $50 million, an MLB record at the time for a non-starting pitcher? This isn’t revisionist’s history: I remember being on vacation at the time when this news went down and it just didn’t feel right, adding the uber-cocky Papelbon to the ‘pen. The name I liked better at the time: Francisco Rodriguez, who similarly broke into the big leagues with aplomb, but then entered a slump in his late 20s … but also showed his arm was back in the last half of 2011 with Milwaukee. He ended up re-signing with the Brewers on a one-year, $8 million deal.

Papelbon was productive, no doubt. But how much money did the San Francisco Giants spend on the three different closers they employed while winning three World Series in 2010, ’12, and ’14? Closers are overrated.

Closers with personality issues –yes, this is a guy who grabbed his crotch at fans and also tried to choke a teammate when he made his way to Washington, a teammate who happened to be one of the game’s best players – is problematic.

3. The Hunter Pence Trades – July 29, 2011 and July 31, 2012

I feel like this doesn’t get brought up enough – how can a front office’s evaluation of a player change so drastically in the span of 368 days? Because this is exactly what played out during the beginning of the end of the Phillies’ five-year run as a National League titan, when they paid quite a bit to acquire Pence from the Astros prior to the 2011 trade deadline only to flip him to the Giants a year and two days later without getting nearly as much in return.

Let’s revisit. The Phillies absolutely needed a right-handed bat – perhaps they should have signed free agent Adrian Beltre the previous winter? – so acquiring Pence was not an outright mistake. And, with that aforementioned pitching staff and a team that would eventually win 102 games, you can even defend Amaro overpaying, which he probably did in parting with two of the team’s top four prospects and three of their top nine prospects in slugger Jonathan Singleton, right-hander Jarred Cosart, and outfielder Domingo Santana (who may or may not have accidentally ended up in the deal).

And this isn’t even about whether any of those players would eventually burn the Phillies or cause them to regret the deal. Singleton has been a big, fat bust while the 24-year-old Santana is having a fine go as a regular in Milwaukee’s outfield this season (.278/.374/.483, 11 home runs).

It’s about giving up that bounty of prospects in July of 2011 and then receiving just one similarly highly ranked prospect in Tommy Joseph just a year later from the Giants. Giving up three top-10 prospects one year, getting just one back for the same player a year later. That math is … not good.

And Pence, 29 at the time of the second trade, was having a fine season (.271/.336/.447, 17 home runs in 101 games), still had a year and a half left on his contract/club control and not at an unreasonable price (meaning he wouldn’t be a burden, in the least, to anyone’s payroll). He would become a key piece of the Giants’ championship clubs.

Amaro gave up a lot to get him and then didn’t get enough back. He probably should have just waited and traded him the following winter.

2. Phillies extend Ryan Howard’s contract – April 27, 2010

I still contend this could have been worse. The fact that this contract kicked in just a few short months after Howard’s career-sinking Achilles’ injury proved to be arguably the worst piece of timing in Phillies history since Eddie Waitkus happened to be in his hotel room when a crazed woman shot him in Chicago. And, when you look at the free agent class Howard would have been a part of and the contracts his fellow first baseman received (hello, Prince Fielder), $125 million wasn’t chump change, but it also wasn’t a 10-12 year deal, either.

Lastly, other teams have rolled out their own contract extensions years before one was necessary. The Colorado Rockies are one such team, doing so with Troy Tulowitzki. They just got lucky in the ability to trade off the oft-injured, declining shortstop before the really big money started to kick in.

Ok, enough defending this contract. It wasn’t good. It wasn’t necessary. It was just less than 15 months earlier that Amaro and the Phillies gave Howard a three-year, $54 million deal. So he was already under contract through the 2011 season, and at a very fair price for the slugger at the time.

Just as the San Fransisco Giants weren’t crushed by a couple of their own bad deals (Barry Zito, $126 million; Aaron Rowand, $60 million) and actually won championships during the time, Howard’s deal didn’t sink the Phillies. Failing to produce anything out of the farm system or adapt to and accept advanced metrics into the front office were bigger problems.

Still, the contract extension was completely unnecessary.

RELATED: Amaro’s firing was MacPhail’s call all the way

1. Phillies trade Cliff Lee to Seattle – Dec. 16, 2009

It wasn’t so much the idea of subtracting a Cy Young Award-winning left-hander who had just dominated in the World Series two months earlier (on the same day you added a Cy Young Award winner in Roy Halladay). Although think about how ridiculous that was in retrospect since they would spent $120 million on said left-hander just 364 days later.

It was the way this “companion” deal went down, as if Amaro and the front office were under the gun, in December, to trade Lee at the same time they acquired Halladay, and had to find the quickest possible suitor, because, you know, these deals had to be announced at the same time, sure don’t want to acquire Halladay the week before Christmas and then announce in the days leading up to to New Years that your Rotation of Aces was being dismantled in a Cliff Lee trade.

But, no, that’s what happened. If you’re going to trade Lee you probably should at least extract the most value for Lee, a then-30-year-old with the aforementioned accolades and skill sets, and, oh, by the way, the financial burden of only one-year and $9 million on the acquiring team’s payroll. So, pretty much the opposite of the financial undertaking/risk of assuming a contract like the one Texas received with Cole Hamels.

The Seattle Mariners must have thought they hit the lottery when they acquired the pitcher the caliber of Cliff Lee, and only had to pay him $9 million on 2010, and only had to part with three guys named Tyson Gillies, Phillippe Aumont, and J.C. Ramirez. Heck, the Phillies could have phoned the Texas Rangers (who would acquire Lee from Seattle just seven months later) and at least played a couple of American League teams off of each other. (Maybe they did, but, if they did, man, they didn’t do very well, did they?).

But at least J.C. Ramirez (now with the Angels) looked really sharp against the Yankees last night.

RELATED: Amaro is gone ... and Phillies fans rejoice on Twitter

A smaller move also considered

The Phillies acquire 1B/OF John Bowker from Pittsburgh on Aug. 29, 2011, prior to the Sept. 1 deadline to acquire players eligible for postseason play.

Again, a small move. But Bowker went 0-for-13 with seven strikeouts in his very brief stay with the Phillies. And the Phils added Bowker rather than giving a long look to Brandon Moss, also a left-handed hitting 1B/OF who slashed .275/.368/.509 with 23 home runs and 31 doubles at Triple-A Lehigh Valley that summer.

All Moss went on to do was hit 51 home runs while sporting an .894 OPS in the next two seasons with the Oakland Athletics, and then make the All-Star team in 2014, too.

But, hey, at least we had Delmon Young.

Follow Ryan on Twitter: @ryanlawrence21

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