Matthew H. Rusk

The man who’s stockpiled the best pitching rotation in baseball history is brash, cocky and oozing self-confidence. There’s just one more thing we need him to do: Win the damn World Series

HE’S SHOPPING at the Langhorne Barnes & Noble in late November with his two young daughters — a moment when Ruben Amaro Jr. would prefer to be left alone. The other shoppers oblige. But not his cell phone. When it rings, he picks up. When you’re the general manager of the Phillies, you’re always on call.

Players ring in the middle of holiday dinners. Agents make last-minute offers well past midnight. Scouts with urgent tips interrupt a New Year’s Eve party. For three years now, Amaro has held the keys to Philadelphia’s sports kingdom in the palm of his hand, and the keeper of the keys has to be ready. Always — especially in this town, where sports aren’t just a metaphor for our well-being. They are our well-being, and for Amaro, a single phone call can mean the difference between coronation and exile.

At the moment, though, he’s not thinking about calls, or Major League deals, or the kinds of earth-shattering acquisitions that would make his reputation. Right now, Amaro’s with Sophia and Andrea, ages eight and 12. (He’s been divorced from their mother, who lives in Bucks County, for 10 years.) His daughters are where he goes for something simpler.

And then his phone rings.

It’s Darek Braunecker, agent for ace pitcher and Philly expat Cliff Lee, a free agent shopping around the league for a new home.

“Hey Ruben. Got a minute? I’ve got Cliff and Kristen here in my office on speaker,” he tells Amaro.

The next voice Amaro hears isn’t Cliff’s. It’s Kristen, his wife.

“Ruben, you broke my heart once,” she tells him. “Please don’t break my heart again.”

WHEN RUBEN AMARO JR. got this job three years ago, the last thing he wanted to do was break hearts. The Phillies had just won their first World Series in 28 years, and the confetti on Broad Street was barely swept up when Amaro was charged with keeping watch over a team that his predecessors, Ed Wade and Pat Gillick, had taken almost two decades to assemble into champions.

And so far, he’s done a splendid job. He brought us to a second World Series in 2009, kept us in the playoffs in 2010, and even acquired two of the top pitchers in the game, Roy Halladay and Roy Oswalt.

Then, on December 15th, Amaro blew up the world of baseball, pulling the most epic of rabbits out of his hat when he stole from the Yankees what they wanted so badly, the player Amaro himself had traded away a year earlier: Cliff Lee. With that, Amaro has assembled one of the greatest pitching rotations in baseball history — potentially, at any rate. And for this, we have crowned him king.

But here’s the rub: His wheeler-dealer success — the Phillies just signed him to a four-year contract extension — only serves to ratchet up the pressure, because come October, Amaro knows he had better be riding on another float down Broad Street. If not, things are going to get ugly. Fast.

Ruben Amaro doesn’t seem concerned. At lunch at the Penrose Diner on a January afternoon, the 46-year-old general manager looks more like a movie star than a baseball executive, every bit the smooth character we saw splashed on TV screens and front pages when he took over in November 2008. The perfectly coiffed dark hair, the bronzed Latin complexion, the wry, disarming smile. His presentation is impeccable — a sharp suit in a subtle green-and-blue plaid, an expensive-looking brown overcoat folded carefully at his side. As he sips a bowl of seafood chowder, his enormous 2009 National League Championship ring refracts the sunlight in a million different directions every time he lifts spoon to mouth.

Amaro comes from a Philadelphia baseball lineage: His father, Ruben Sr., was a Phillies shortstop back in the ’60s, and Ruben Jr. himself played briefly for the team two decades later. He’s been accused of being a bit smug, like he knows something you don’t. The cat who ate the canary. But that attitude — and his supposed intensity, for that matter — aren’t readily apparent.

Instead, Amaro seems like a regular guy from Philly — witty, unvarnished and self-deprecating. “Dude,” he says, “my job is to just not screw this up.” He laughs at this, a laugh of two parts workman’s gravel, one part smooth politician.

The more he talks about the pressures of this job — the immense stress of not screwing up — the more obvious it becomes that keeping his pride in check is less about diplomatic deference and more about necessity. Amaro knows praise in Philly is fleeting. He lived through it just a year ago, when fans came knocking at his door like a horde of angry, pitchfork-wielding villagers after he traded Lee to Seattle for three minor-league prospects — and broke Kristen Lee’s heart.

“I think people in Philly get fired up that I’m a hometown guy. It’s cool to see one of their own doing this job,” Amaro says. “But I know I’m never going to get a free pass because of that. And I shouldn’t.”

RUBEN AMARO MAY HAVE a handle on where he’s landed, but the pride and intensity — they’re still there, all right. And to really figure him out, to understand how he got the job of general manager and why he seems so good at it, you start by taking a look at the soccer-playing kid.

On the nights before young Ruben Jr. was to start in a soccer match, the Amaro household in Northeast Philadelphia was silent. Shades drawn. Radios off. Total lockdown. Ruben Jr. couldn’t stand even the slightest sounds or cracks of light. The headaches were blinding. Nauseating. Ruben Sr. would try to calm him down. “It’s only a game, Ruben,” he’d say.

But back then, Ruben Jr. treated the game like it meant the world.
“He’s always been very intense,” recalls Ruben Sr. “About everything he’s done.”

Ruben Jr. didn’t hang around with many kids his age. He didn’t need any more friends, he’d tell his parents. He had his brother David’s friends. And David, who was three years older, was his best friend. “He was bored with kids his own age,” David recalls. “Because it wasn’t competitive enough.”

Until he was 15, that competition remained soccer, even though baseball was, as Ruben Jr. says, “the natural order of life” at home. His grandfather, Santos, was a feared hitter in the Mexican league for 17 years, and his father won a Gold Glove at shortstop for the Phillies and was later a first-base coach on the 1980 championship team. Ruben Sr. would bring his young sons along to Mexico for three-month stretches in the winter, where he managed in the Mexican and Venezuelan leagues.

But even though Ruben played baseball, it was his father’s sport. Soccer was his. It was soccer that kept him up nights before a game with migraines. Soccer that was beautiful and perfect.

And he was good at it. His father says it wasn’t unusual for Ruben Jr. to score three or four goals in the first half of most matches, then retire to “parade like a peacock for the next 45 minutes. And I said, ‘Hey, if you’re not going to play a full hour and a half, I’m not going to watch your games anymore. You are supposed to have respect for your teammates. You play the whole game.’”

Amaro was offered an opportunity to play soccer in Germany, where he would attend high school for a year and a half while the experts across the pond evaluated whether or not he had the stuff to become a professional. His mother, Judy, however, didn’t approve. Being Jewish, Judy wasn’t comfortable sending her son to a country with such an ignominious history, so Amaro remained stateside.

“After that, he didn’t want to see or smell a soccer ball ever again,” says his father.

Shortly thereafter, Amaro got a gig as batboy for the Phils. He would lean on a fence next to the likes of Pete Rose, Steve Carlton and Mike Schmidt, watching the legends at work. And it was then that he finally started to understand what his father told him when he’d asked, “Why do you waste your time with baseball?”

“Because, Ruben,” he said, “baseball requires you to think.”

His parents had stressed education from an early age, sending him to Frankford Friends Elementary and Penn Charter High School, encouraging him to become a doctor or lawyer someday. He was seriously thinking about becoming a veterinarian, but when he saw those guys in 1980, and then stood on the field as they won the city’s first World Series, he started thinking: Maybe there was something special about baseball after all.

Some of his Stanford teammates — where Amaro enrolled in 1983 — called him cocky, thought he showed a little too much hubris. But his then-teammate and longtime friend Dave Esquer says, “People can mistake that and call it whatever they want. But Ruben was going to will himself into the big leagues, whether that should have happened or not.”
In the majors, Amaro was always a fringe player. A bench man. Never good enough to make the starting lineup, he had to fight for that 25th spot on the roster. By 1998, with his Phillies contract about to expire, he knew he had to consider what would come next.

Wade, who remains a close friend of Amaro’s and is also godfather to his younger daughter, says he saw in Amaro a player who had not only the aggression of a winner but also the brains of an executive.

“Ruben was a guy who I knew would have a completely different perspective than I did, coming from the field,” recalls Wade. “He could be a little brash, but I liked his aggressiveness.”

When Amaro got to the front office in ’98, there wasn’t much room for his pride, and it was his years under Wade and Gillick that helped him temper the fire. He learned that a GM couldn’t live and die with every game or trade. That a GM is the one who needs the steady hand, the patience everyone else around him may lack. The coaching staff, the manager, the players — they could get as emotional as they wanted to. But not the GM. If the GM panics, everyone else panics.

“Ed did something instrumental for me in my first year,” says Amaro. “He assigned me to go down to spring training and scout with [former general manager and advisor] Paul Owens. I just spent hours and hours with him, talking about how to look at guys not just as a former player, but as someone from the front office. That was invaluable.”

After Wade was fired following the 2005 season, Amaro was one of just a handful of guys who interviewed for the job. The position went to Gillick, which Amaro says in retrospect was a “blessing in disguise.”

“Back then I thought I knew everything. That I could scout players. Make deals. That I could make all the decisions myself. Now I look back and think, ‘What an idiot.’ I wasn’t ready. I thought I was, though, pride-wise.”

THIS PAST WINTER, if Amaro was actually going to outfox the impossibly rich New York Yankees in reacquiring Cliff Lee, he knew he would need every ounce of restraint and composure he could muster. So he used his best — perhaps his only — leverage: the Lees’ emotions.

By late November, the two teams in the hunt for Lee were the Yankees and Rangers. Texas, who had acquired the left-hander from Seattle before the 2009 trade deadline, was looking to sign Lee to a long-term contract. And the Yankees, well, they were looking to do what the Yankees do best: spend buckets of money to put baseball’s hottest commodity in pinstripes.

But Kristen Lee didn’t want to go to New York. The last time she found herself in Yankee Stadium — a game in 2010 where her husband was pitching against the blue and white for the Rangers — she’d been spit on by a fan. Amaro knew this. And he also knew how much the Lees enjoyed casual walks around Rittenhouse Square, the Art Museum, and the passion of the fans who loved Cliff like he was one of their own. Coming back to Philly would be like coming home. Amaro knew he could use this to his advantage.
The fans had fallen for Lee after Amaro acquired him midseason in ’09, helping the Phils get back to the World Series, and the reaction to trading Lee the following off-season was ugly. A few weeks after trading the pitcher — and claiming publicly that it was a necessary deal to restock the team’s minor-league system — Amaro and his brother were in Dick’s Sporting Goods buying a bike for one of Amaro’s daughters.

“Yo, Ruben, what the hell’s up with trading Lee?” one guy challenged him in the checkout line. Another guy then launched into the myriad reasons why he thought it the stupidest thing the GM could have done. At this, Amaro turned on his signature charm, explaining that it was unfortunate but necessary, that it’s never just black-and-white. Maybe he could’ve used them to handle the negotiations, he joked.

It was the same everywhere Amaro went. Diners, fancy restaurants, alone or out with his family. Strangers telling him how to do his job. “He’s very level-headed about it all,” says his brother David. “It’s me who gets the last word with these clowns.”

Last winter, the clowns were everywhere. Even though Amaro wound up acquiring Halladay at the very same time — bringing to town the best pitcher in the game — it almost didn’t matter.

“Our mother was very upset by all of it,” recalls David. “But Ruben’s played baseball in Venezuela, where you get batteries and beer cans thrown at you. Listening to some guy on the radio scream ‘You’re a moron!’ 25 times in a sentence isn’t really a big deal.”

The only thing that is a big deal to Amaro is the toll all of this might take on his daughters.

“When I got this job, I told my kids, who were nine and five at the time, ‘Remember, right now they like Daddy. In two months they might not like Daddy at all. But just always remind yourself that your Daddy is still the same Daddy.’”

Especially in Philadelphia.

TWO WEEKS AFTER Ruben Amaro took that call from Darek Braunecker, Cliff Lee’s agent, in Barnes & Noble, he began negotiating with Braunecker. Amaro offered a five-year contract at a figure that was probably far below what either of the other two teams was now promising. (Amaro won’t disclose the amount.)

The Lees declined.

And that was okay. Amaro had a feeling they would be back.

Still, there was an endless stream of nights spent pacing his Citizens Bank office with assistant general manager Scott Proe-frock, wondering what more they could do to make this happen, and worrying — always worrying — about what they would do if it didn’t work out.

“What was most agonizing was not being able to tell anyone about it,” recalls Amaro. Not his brother. Not his father. Not his college buddy Esquer.

What’s more, if it got out that Amaro was trying to bring back the same guy he’d sent packing to Seattle less than a year earlier, it would look like an admission that letting him go in the first place was a mistake. And if the deal didn’t work out, Amaro was going to look like a failure.

Amaro had assembled the smallest possible circle of advisors for pursuing Lee. Gillick, Proefrock and Phillies president David Montgomery. That was it. No one else, not even manager Charlie Manuel, could know what was brewing. Though there was one other person he told. On the last weekend of negotiations, Amaro called Roy Halladay and asked what he thought of the team pursuing Lee, knowing they’d have to give him more money and years than they’d given Halladay.

“Ruben, I just want to win,” the pitcher told Amaro. “I don’t care what you give the guy.”

So much for needing to massage the ego of Halladay, who was merely the National League’s best pitcher last year.

And then, shortly after rejecting the Phillies’ initial offer, Braunecker called Proefrock. Lee was still willing to consider, he said.

This was Amaro’s element.

“Ruben and Scott were sitting there like they were in a NASCAR race,” recalls Gillick. “Just sitting in third place, idling, letting New York and Texas blow their wads and do what they had to do.”

Amaro also knew not to overplay the cunning and intrigue of the deal. “Sometimes GMs think it’s such a poker game that they try too hard to create illusions,” says Oakland A’s general manager Billy Beane. “With Ruben, he’s not going to play games with you. That’s why people like dealing with him.”

To that end, Amaro had been frank with Lee and his agent from the beginning. He’d told them, “Look, you guys are the ones who are going to have to make this happen. Not me. You guys are the ones who will have to bite the bullet, because we’re probably not going to be able to match the money or contract years of the other guys.”

At one point, he told them he wasn’t going to offer more than five years guaranteed. Really, he didn’t want to offer more than three years, a longstanding policy of the Phillies with respect to pitching contracts.

Still, it wasn’t happening. Every time Amaro made an offer, the Lees asked for just a little bit more. The Rangers were offering Lee $138 million for six years. And the Yankees were offering him the choice of either a six-year, $138 million deal or a seven-year, $148 million contract. Amaro simply wouldn’t be able to bridge the gap.

So by the afternoon of December 12th — three weeks after Kristen Lee had pleaded with Amaro not to break her heart again — “The deal was dead,” Amaro says. “We said, ‘That’s it. We’re done. It’s dead. Out. Done.’”

Conceding defeat, Proefrock sent Braunecker a text. “I feel sick about this,” he wrote. Braunecker’s response: “I feel the same way.” It was that response, so emotional, so devoid of cunning and games, that gave Proefrock the feeling that maybe, just maybe, there was still a shred of hope. They would make one last offer: $120 million. Five years.

Later that night, Amaro’s cell phone rang. “Ruben?” Once again, the voice of Braunecker on the other end. “You got Cliff back.”
IT’S IRONIC, PERHAPS, that the first bit of feedback Amaro received after the good news broke was not one of praise, but derision. It came in the form of a text from the recently expatriated Jayson Werth. All it said was this:


“That reaction from Jayson was funny,” says Amaro in his office in February, again flashing that smile. “He was pissed off. He had just signed with Washington. He said to me, ‘You dumbass. You could’ve had both of us.’ And I said, ‘You’re the dumbass. You could have taken our arbitration offer.’”

At any rate, the stakes for Amaro’s future are now even higher than when he first took this job, just five days after the 2008 Broad Street parade. The Phillies have made 13 trades and committed more than $255 million to have this new rotation of Halladay, Lee, Oswalt and Cole Hamels (oh yeah, and Joe Blanton).

But what if these guys don’t pitch up to expectations? What if the bats go as stone-cold as they did during last summer’s slump, or in the NLCS against the Giants? What if losing Werth proves more detrimental than expected?

“They love me now,” Amaro says, looking out at a South Philly winter fog. “We’ll see what happens in three months.”


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