Wait, he was a Red Sox first baseman?
Tony Perez (1980-1982)
The first Hall of Famer on the team, Tony Perez is best remembered as the first baseman of the Big Red Machine, winning two World Series with the Reds in 1975 and 1976. After spending three years up north with the Montreal Expos, Perez was signed by the Red Sox heading into the 1980 season.
Perez would perform well for the Red Sox, hitting to the tune of a .266 batting average and a 105 OPS+ in 304 games with the Red Sox, even receiving MVP votes in 1980. Perez would have a stint in Philadelphia before returning to Cincinnati and retiring at age 44 in 1986.
Honorable Mentions: First base kind of ran into the same lack of selection as catcher, but I will use this space to mention the first ever Red Sox player to win American League Rookie of the Year, Walt Dropo. In all honesty, no pick for this position would have been better than Tony Perez, so he was an easy choice.
Wait, he was a Red Sox second baseman?
Brandon Phillips (2018)
The guy that inspired this entire article, Brandon Phillips not only continues the Reds-Red Sox crossover from Tony Perez, he also represents the shortest Red Sox tenure out of anyone on this list. Phillips was a stalwart for the Reds, racking up multiple All Star Game appearances and Gold Gloves during his 11 years in the Queen City.
Phillips played all of 9 games with the 2018 Red Sox, but gave fans a great memory in his game-winning home run against the Braves that capped a 6-run Red Sox comeback. This Red Sox stint would be his last games in the Majors, hanging up his cleats after the 2018 season. While his time with the Red Sox was very short-lived, Phillips gave us a moment to cherish for that extremely dominant 2018 team.
Honorable Mentions: My dad was from just outside of Cincinnati, and I still have family out there, so any Reds-Red Sox connection will hold a special place in my heart. With that being said, there are plenty of options that could have taken this spot.
You can look back to the 2018 Red Sox and take Ian Kinsler for this slot. You could also take the man who was the final piece in the Adrian Gonzalez-Josh Beckett-Carl Crawford trade with the Dodgers in Nick Punto, but the answer in my heart was always going to be Dat Dude BP.