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Players who get their numbers retired usually come from a team’s period of dominance, and the 1960s/70s Pirates still have three reasonably strong candidates left.
Dave Parker started with Pittsburgh in 1973 and played there until 1983. In that time, he racked up 36 fWAR and 32.6 bWAR. He finished his career in 1991, with 46 fWAR and 37.8 bWAR. And I can’t claim to know the specifics of every team, but for what it’s worth, my dad is quite adamant about retiring his number. I have no idea what the Pirates think about Parker’s case, though.
My dad is even more in favor of retiring Al Oliver’s number. In his ten years with the Pirates (1968 to 1977), Oliver was worth 32 fWAR and 25.0 bWAR. He would play until 1985, and for his career, he was worth 50.2 fWAR and 38.8 bWAR.
Manny Sanguillen was a teammate of Oliver and Parker, playing with the Pirates from 1967 until 1980 (with the exceptions of 1968, when he was in the minors, and 1977, when he played in Oakland). He was worth 24.6 bWAR and 32 fWAR (with 24.3 bWAR and 32 fWAR from his days in Pittsburgh).
The last two former players that I would like to cover are much more recent. The first is Brian Giles. Giles had a very short stay in the Steel City (1999 to 2003), but they were far and away his best years. In his four and a half seasons in black and gold, Giles was worth 26.6 bWAR and 30 fWAR. For his career, the right fielder was worth 42.7 bWAR and 59 fWAR.
While I never really became a Pirates fan when I lived in Pittsburgh, I did become a fan of Giles and Jason Kendall (the other recent player I’m going to mention). Both were incredibly overlooked for their careers, and each has their claim for most underrated player in the history of the game. Giles’ argument in this discussion would be that he has a borderline-Hall of Fame career, yet has been almost forgotten in the two seasons since his retirement.
Jason Kendall, according to one measure, is the best active player to never receive a single MVP vote. Baseball-Reference gives him 37.7 career bWAR, with 31.5 of those coming in Pittsburgh. Fangraphs gives him 43 career fWAR, with 34 of them coming in black and gold.
I would like to see Giles and Kendall remembered in some way, but I’m not sure if either made a strong enough impression. Also, they played during the Pirates’ worst stretch in history. The management might not want to remember that period in history.
Among current players, Andrew McCutchen is the only one worth serious consideration at this point. Jose Tabata, Neil Walker, Pedro Alvarez, and Jameson Taillon may all be worth considering some day, but as of right now, none of them is a serious threat for number enshrinement.