No. No no no no no. Garagiola is a very poor match for the Pirates.
Garagiola was the Diamondbacks' GM from their inception in 1998 until 2005. He showed an intense interest in veterans from the very beginning of his tenure, losing first-round draft picks in the earliest years of the D'Backs existence so that he could sign the likes of Jay Bell and Russ Springer. This strategy worked shockingly well at first, as the D'Backs won 100 games in their second year of existence (largely because of great seasons by veterans like Bell, Matt Williams, Luis Gonzalez, and Randy Johnson), and won the D'Backs the World Series in 2001 with outstanding years by Gonzalez, Johnson and Curt Schilling. The '01 Diamondbacks' entire starting lineup was over 30.
However, Garagiola continued to stick to the Must! Have! Veterans! strategy until it was revealed as... not so much a strategy, really, but a fetish. Or, to put it a different way, Joe Garagiola Jr. is to veterans as Cookie Monster is to chocolate chips. Garagiola refused to get rid of an ancient and unproductive Mark Grace even though Erubiel Durazo was obviously better; he then dealt Durazo for Elmer Dessens, who was coming off an artificially good-looking season with the Reds, and Dessens predictably went right back to being the mediocre pitcher he always was. He traded Lyle Overbay and Chris Capuano to the Brewers for one year of Richie Sexson; Sexson missed almost the whole season due to injury, while Capuano and Overbay both blossomed into good players with the Brewers. After an 84-78 season in 2004 that should have told Garagiola that that was enough with the veterans, he signed Russ Ortiz to one of the stupidest contracts in recent baseball history. He then dealt Randy Johnson, but, on the same day, he for some reason decided to trade four players for an expensive and past-his-prime Shawn Green.
It's true that in the last few years of Garagiola's tenure, he managed to put together one of the better collections of talent in the minor leagues, headlined by Justin Upton and Stephen Drew. He also drafted Brandon Webb. But all of his first-round draft choices until 2002 were busts, and in the only two major deals where he traded veterans and got youngsters in return (the Schilling and Steve Finley trades), he got nothing but junk.
Garagiola's tenure as a GM was mixed. He obviously was wildly successful at the beginning of his tenure, but he stuck with his strategy well past the point where it was helpful, raising the question of whether acquiring veterans was, for Garagiola, a strategy or an ideology. Buidling a team around veterans simply will not work in Pittsburgh - in order to get the equivalent of 1998-vintage Randy Johnson, you've got to pay serious bucks, and the Pirates won't do that. He's a poor fit for the Pirates.