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

Back in the early 1980s at Veterans Stadium, a kid with the same name as a former Phillies shortstop and then-coach was a bat boy wearing a team uniform inside the home dugout. That was Ruben Amaro Jr.’s introduction to the Phillies family.

Amaro, a Penn Charter graduate, would finally leave Philadelphia to attend college at Stanford University. But he’d return to put the major league uniform on again at the Vet, this time as an outfielder, in 1992 and played in 25 games with the ’93 National League pennant winners, too.

Amaro had a second stint with the Phillies from 1996-98 before ending his playing career at the age of 33 and beginning his new life as a front office man, working under then-general manager Ed Wade.

Just as he’d rise from batboy to big league outfielder, Amaro would climb to one of the most prominent chairs in the front office, too, when he succeeded Hall of Famer Pat Gillick as the Phillies general manager a few short days after the 2008 team clinched the franchise’s second World Series.

Amaro’s Phillies returned to the Series in ’09, won two more division titles in ’10 and ’11, and won a franchise-record 102 games in the latter of those last two seasons. But then the free fall began: the injuries to prominent stars, the bad contracts and bad trades, the losses.

They all piled up and Amaro’s honeymoon as the GM for his favorite team in his hometown was short-lived. He began to be a regular punch line for talk show hosts, bloggers, and columnists alike, and it was nearly an everyday thing for the final four years of his tenure in the Phillies’ front office.

“I always felt like that was part of the gig,” Amaro said on Wednesday when he returned to Citizens Bank Park as the Boston Red Sox hitting coach.

It was his first time back at the ballpark since being fired in September of 2015.

“In Philadelphia,” he continued, “that's what happens. You're under a great deal of scrutiny. That's what it's all about. It wasn't anything new. I saw Pat and Ed, in particular, have to deal with that. So it was nothing new. I don't think as a person you really like to get ripped. I don't think anybody likes to get ripped, I don't think you guys like to get ripped for what you write or what people tweet at you guys about how much you don't know. I don't think anybody likes that. But, you know, it's an occupational hazard. You've got to deal with that, I guess.”

There was a fair reason for a lot of the criticism. We looked at the five worst moves in the beleaguered Amaro’s tenure as general manager on Tuesday.

But he made some good moves, too. Really.

So let’s look at the five best Amaro transactions during his seven seasons as the Phillies’ general manager.

***

5. Phillies trade Jonathan Papelbon to Washington – July 28, 2015

You’d think it’d be easy to trade a closer two weeks removed from his sixth All-Star appearance, one who held franchise save records for two of baseball’s oldest organizations, the Phillies and Boston Red Sox. But then you’d forget about said closer’s declining stuff, his hefty salary and a vesting option for the next year, and his well-known status as a malcontent.

Ruben Amaro Jr. was able to trade Papelbon, and that in itself earns a spot on this list. And he traded him to a divisional foe, no less. And we all watched Papelbon bring his drama to Washington and attempt to strangle Bryce Harper in the Nationals’ dugout after doing his part to blow a game against his old Phillies team.

Again, the fact that Amaro was able to trade him was a minor miracle. Any team that acquired Papelbon wasn’t getting a two-month rental but also a player they had to pay $13 million to in 2016, too. Amaro got the Phillies out from under that contract (a contract that earned a spot on our other Amaro list) and got him out of a young and impressionable Phillies’ clubhouse, too.

Oh, and not only did he do all of that but Amaro got an actual living, breathing, talented pitching prospect back from Washington in right-hander Nick Pivetta. This was such an easy entry for this list.

4. Phillies sign free agent Cliff Lee – Dec. 15, 2010

Remember that night, when the Mystery Team in the Cliff Lee Free Agent Sweepstakes happened to be the Phillies? Most Phillies fans could probably tell you where they were when they found out the surprising news that came out about midnight on that December night.

Although it’s difficult to sit here and say it made up for the second of Amaro’s three Cliff Lee transactions (which obviously earned a spot on our other list), signing Cliff Lee to a five-year, $120 million contract to put him in a rotation with Roy Halladay, Cole Hamels, and Roy Oswalt (OK, and Joe Blanton, too). The marketing department loved Amaro and his staff – they couldn’t sell t-shirts with the Rotation of Aces on them fast enough before Christmas. Ditto the ticketing office.

I’d still argue – and I began making this point probably a year or two after the deal – that Lee wasn’t the big ticket free agent the Phillies needed or should have signed that winter. They already had three formidable starting pitchers in the rotation. They had some declining, aging bats in their lineup, a lineup that would have looked quite nice with the right-handed hitting Adrian Beltre plugged in between Chase Utley and Ryan Howard in the cleanup spot. (Sure they had Placido Polanco on the roster, but he could have turned into the same super utility player Michael Young was when it was his Texas Rangers who signed Beltre to a 5-year, $80 million deal. Heck, they would have needed it with Utley’s knee injuries).

With all of that said, and factoring in that the last two years of Lee’s deal were basically total losses, this was a good deal. Lee went 37-25 with a 2.80 ERA, eight complete games, seven shutouts, a 1.05 WHIP, and a ridiculous 6.54 K/BB rate in 93 starts from 2011-13. This was a player dominating the opposition in his prime, who gave the Phillies a chance to win every fifth day, who put butts in the seats, etcetera, etcetera, as a fan favorite.

3. Phillies acquire Roy Oswalt – July 29, 2010

I feel like this will be the most controversial (for lack of a better word) item on my Amaro do-good list. Because the Phillies did part ways with some premium talent in this pre-trade deadline deal, sending left-hander J.A. Happ and prospects Anthony Goes and Jonathan Villar to the Houston Astros.

Villar had a breakout year with the Milwaukee Brewers last year but is having a not-so-great season with the Brewers this year. Gose never turned into the Michael Bourn-in-his-prime player some projected, but Happ has made a pretty good career for himself seven years later, and some could argue he would have fit into the rotation just fine instead of Oswalt come 2011 (since he was excellent in 2009).

Still, let’s not ignore the need the Phillies had in 2010 (albeit it was because of the worst/No.1 move on our other Amaro list) and just how great Oswalt was in a Phillies uniform that summer. Here’s something you probably wouldn’t have realized: Oswalt was better in the final two months of the regular season in 2010 than Cliff Lee was in the final two months a year earlier.

After the Deadline: Lee was great in '09, but Oswalt may have been better in '10

	Year	Games	W/L	ERA	WHIP
Lee	2009	12	7-4	3.39	1.13
Oswalt	2010	13	7-1	1.74	0.895

Oswalt was ridiculous upon arrival to Philadelphia, helping the team clinch their fourth straight pennant. He was more of the same up until his final postseason start that fall, too. Oswalt’s second and final year of the Phillies was basically lost to injury, but Amaro got him for the stretch run in ’10 and it worked out quite nicely.

2. Phillies trade for Roy Halladay, sign him to extension – Dec. 16, 2009

It’s crazy to think this isn’t No.1 on the list, given Halladay’s stature as one of the best pitchers of his generation, something he’d show off in winning a Cy Young Award in his first season with the Phillies in addition to pitching a perfect game and one of only two postseason no-hitter in baseball history in 2010, too.

Perhaps some of the actual Halladay acquisition (sending prospects Kyle Drabek, Travis d’Arnaud, and Michael Taylor to Toronto) was muted a bit by the companion Cliff Lee trade made on the same day. But let’s not forget that in addition to trading for Halladay, Amaro was able to lock up the former American League Cy Young Award winner to (at the time) a team-friendly contract extension (3-years, $60 million).

Sure, the Phillies could have simply kept Lee and stopped their pursuit of Halladay. But Amaro wanted Halladay all along (Lee was his fall-back plan the previous summer). And Lee didn’t have any interest giving up free agency while Halladay was open to doing so and signing said team-friendly deal (for half of what Lee would eventually get paid … by the Phillies).

The Roy Halladay deal in itself was a winning transaction. With maybe the exception of the second Jim Thome signing, adding a future Hall of Fame to your team is never a bad deal, really. Halladay surely lived up to all the hype, even if Father Time came calling for him in his last two, injury-ravaged seasons with the Phillies.

1. Phillies sign Pedro Martinez, trade for Cliff Lee – July 2009

So, wait, what was that I was just saying about adding Future Hall of Famers to your roster? Amaro nearly added two in the same month as he closed in on his first trade deadline as a major league general manager. He wanted – really wanted – Roy Halladay and he had free agent Pedro Martinez in his crosshairs, too.

Amaro got his second man during the All-Star break in 2009, convincing Martinez to put off retirement for one more summer to join the World Series-or-bust Phillies. Martinez went 5-1 with a 3.63 ERA in nine regular season starts, looking electric at times. He was dominant in his NLCS start, too … but had mixed results in the World Series. Still, you pluck Pedro off the free agent wire, you’re doing something right.

But Amaro wasn’t finished. He didn’t end up with his top target but acquired Lee instead two days before the trade deadline, sending over a package prospects that included right-handed pitching prospect Carlos Carrasco.

Carrasco has blossomed into a very good pitcher for Cleveland, but if you think that means this wasn't a good trade you're guilty of revisionist history. You have to give up something to get something, and Lee was a proven pitcher, a former Cy Young Award winner in his prime, and a guy who would dominate down the stretch and during the World Series against the Yankees, too.

The fact that this was Amaro’s backup plan to Halladay proved the general manager was pretty savvy in his preparation for his first trade deadline.

A smaller move also considered

Some folks wanted me to put Amaro’s inability to retain free agent Jayson Werth in the winter of 2010-11 (the same year he signed Lee) down on the other list as one of Amaro’s worst moves. Well, not paying Werth $127 million was just fine. Sure, the contract worked out OK for Washington, but Washington also had a bunch of pre-arbitration players on their roster, not a bunch of players already making pretty good bank (Howard, Utley, Rollins, Halladay, Hamels, etc.). Again, Beltre would have been the bat to add as a free agent that winter anyway.

But, speaking of Werth, Amaro did actually keep Werth off the free agent market a year early when he signed the late-blooming, 29-year-old outfielder to a two-year, $10 million deal two months after the Phillies won the World Series. Werth didn’t have a huge track record at the time, but he did hit .282 with a .379 OBP and 32 home runs in 228 games with the Phillies in 2007-08 (and hit well in the postseason, too).

A smaller deal, sure. But sometimes the smaller deals are the best ones.

By the way, we purposely didn’t include any of the rebuilding trades Amaro made in his final 12 months on the job (trading Hamels, Utley, Rollins, Byrd, etc.) because it’s too soon to call any of those trades clear ‘wins.’ OK, we did include the Papelbon deal, but that had more to do with the player exiting than the one coming into the organization.

Follow Ryan on Twitter: @ryanlawrence21

Like the new PhillyVoice Sports page on Facebook.