Matthew H. Rusk

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.