Gillick also built a World Series champion in Philadelphia (2008) and playoff teams in Baltimore and Seattle. His 2001 Mariners had 116 regular-season wins, tied with the 1906 Cubs for the most victories in a single Major League season. But it was perhaps his biggest trade that sent Gillick off on a career that will land him in Cooperstown's coveted plaque room: Fred McGriff and Tony Fernandez for Alomar and Joe Carter.
"That was a very quick deal," said Gillick, who executed it with then-new Padres GM Joe McIlvaine during the 1990 Winter Meetings in Chicago. "Joe had gone over as general manager. Greg Riddoch was manager of the Padres. Joe and I went back a long way and had a good relationship. I was looking for a right-handed hitter and was interested in getting Carter. Joe said he wanted McGriff. There was an age differential there. I asked him if he'd throw in Alomar. He asked me, 'Well, if I throw in Alomar, would you throw in Fernandez?'"
With Jack McKeon as GM, the Padres had acquired Carter the previous offseason, sending catcher Sandy Alomar Jr., Roberto's older brother, to the Indians. The two boys had been signed and developed by the Padres. McIlvaine, who replaced McKeon late in the 1990 season, needed a shortstop (Fernandez) to replace an aging Garry Templeton. He had no doubts about trading the right-handed-hitting Carter for the lefty-swinging McGriff in a swap of power hitters.
The only qualm was trading the younger Alomar, who turned out to be the premier second baseman of his generation. Alomar was heading into his fourth big league season and considering the Padres' tenuous finances, McIlvaine figured he didn't have the money to sign him as a six-year free agent anyway.
"I said, 'Let me think about it. I'll get back to you in a couple of hours,'" Gillick recalled. "So I had a meeting with our group and went back to Joe. I tried to get a third player out of him. I tried to get a pitcher. I couldn't do it. We agreed on two for two. The whole negotiations probably took about three or four hours and we announced the deal the next day. We just kept it quiet. In fact, I told our public relations guy not to run anything off in the P.R. room. People are always hanging around in the P.R. room."
It may be no irony that Gillick and Alomar are part of the same Hall of Fame class. Gillick long pursued Alomar. With Gillick ensconced as the new GM of the Blue Jays when they expanded into the American League in 1977, he tried to sign Alomar as a kid playing sandlot ball in Puerto Rico. But McKeon was way ahead of him, inking Robbie as an amateur free agent in 1985 long before Puerto Rican players were included in the First-Year Player Draft. The Alomars came together as a package with Sandy Alomar Sr., a former big league infielder, installed as a Padres coach.
More than a decade later -- shortly after Gillick left the Blue Jays for the Orioles -- he signed Alomar as a free agent for the 1996 season. With Alomar playing second base, the Orioles lost in the AL Championship Series in 1996 and '97. They haven't been back to the playoffs since.
"Not only was he a great general manager, but he's a great person," Alomar said about Gillick. "He wanted to sign me [as a kid], but I already had a commitment with the San Diego Padres. Five years later, he went back and got me for the Toronto organization. Those were great years in my career. I have a lot of respect for him."
McIlvaine was certainly prescient about being able to keep Alomar. In 1993, ownership tore apart the team and McIlvaine quit rather than break up what he had put together. McGriff was traded to the Braves and Fernandez went back to the Blue Jays via the Mets, playing with Alomar and Carter on the 1993 team that defeated the Phillies in a six-game World Series.
Everyone remembers the walk-off homer Carter hit off Mitch Williams to win that title. But few remember the two-run homer Alomar blasted off Oakland's Dennis Eckersley in the ninth inning to tie Game 4 of the '92 ALCS. The Blue Jays went on to win the game in 11 innings and the pennant in six games. Alomar, who hit .423 with a pair of homers and five steals, was named the MVP of that series. Toronto went on to defeat the Braves in six World Series games to win the Blue Jays' first title.
Despite playing for seven teams, Alomar is the first player to enter the Hall with the Blue Jays emblem embossed on his plaque.
"He was pretty spectacular both offensively and defensively," Gillick said about Alomar. "I don't think we'd have ever gone to the World Series in '92 if he didn't hit that home run off Eckersley in Oakland that day like 4:30 in the afternoon when you could hardly see at the plate [because of the shadows].
"That was a big, big blow for us. Certainly so was Joe's in '93, but that one off Eckersley put us there."