I was really bummed about losing out on Puckett, too. He may have been my favorite non-RS player (along with Tony Gwynn). Those early 90s Sox team were bad, though, so I doubt that he would have put them over the top. Would have been fun to see him hit in Fenway, though.
Apparently they offered Puckett 5/$35m & he took 5/$30m to stay in MN.
Tony Gwynn was by far my favorite non-RS, followed by Craig Biggio.
As far as I can tell, the closest Biggio ever came to the Sox was playing in the Cape Cod League for the Yarmouth-Dennis Red Sox, & of course playing in college with Mo Vaughn & John Valentin @ Seton Hall.
He was drafted 22nd overall by the Astros in 1987 & went on to spend the next 20 years there.
The Red Sox didn't draft until 26th where they acquired Reggie Harris, who actually pitched for the Red Sox in 1996 after stints with the A's (who Rule V'd him from the Sox) & the Wei Chuan Dragons.
After signing as a free agent, Reggie Harris pitched 4 games for the Red Sox in '96, allowing 7 hits, 5 walks & 6 earned runs in 4 1/3 innings.