I think Jimmy Piersall should get a little more SoSH love. As a CF for the Sox for 8 years in the 1950s, he was a GG winner and a 2-time AS. Furthermore, like other baseball greats, Ruth, Cobb, Gehrig and Monty Stratton, his life was immortalized by Hollywood.
Do not strike out on this candidacy!!!
From 1950-1958, Piersall put up a 273/340/397 line, good for a 93 OPS+. He did average 12 HRs per 162 games, which I'd imagine must be respectable for a CF with reportably good defense in that era.
I would argue that it's still a complete no-brainer that Lynn, Smith, and Damon go in ahead of him. I would still argue that Ellis Burks was a far superior player over 6 seasons with the team, with his power and above-league-average offense with a 116 OPS+. Burks also was an All-Star with a Gold Glove to his name while in Boston, for what relatively little that award may be worth, given the voting scheme. I think it would take a pretty healthy gap in defensive competence between Burks and Piersall to get him in over Ellis.
That leaves Ellsbury, which I think comes down to a "longevity and steady performance" vs "short term spikes in performance." Ellsbury has a superior offensive performance (OPS+ 109) compared to Piersall, but in only 3 full seasons vs 6 for Piersall. Ellsbury also has a GG and ASG appearance to his name, plus a World Series win (1.188 OPS against the Rockies).
So, unless you heavily weight durability over performance, I think a fair evaluation of Piersall finds him lacking relative to these 5 other candidates. Let's not let our current frustrations with Ellsbury's durability obscure what he has done so far for the team when healthy. Piersall does seem to have been overlooked so far relative to his contributions to the franchise, so I'd agree with Bankshot on that point.