To be fair, let me recap a little history for you. In 2001 the Hall of Fame changed the rule to reflect that they would make the executive decision of what logo a player would wear on the cap on his HoF plaque. The reason for this is because some teams were playing unfair and trying to buy out HoF elect's logo decisions. The Tampa Bay Rays offered Wade Boggs money to wear the TB logo on his cap which was clearly unfair and corrupt.
"I don't want to do anything that might be an embarrassment to someone or show someone up, that's not my character. But there will be some way I will try to acknowledge the Cubs fans to show just how important they were to me. I did think about at some point in time during the speech putting a Cubs cap on, but I don't know if that's appropriate."
Either logo would have been appropriate in my opinion, but to look at things historically, the Montreal logo made the most sense. There are many who look at Dawson as the Montreal Expo. The Expos moved to Washington DC in 2004 and renamed themselves the Nationals, and aside from Gary Carter, Dawson is the only other player to be inducted with an Expo's logo on his cap.
"I haven't heard from President Obama probably because he's a White Sox fan."
Dawson remarked to the Chicago ESPN affiliate.
Like I said, this blog isn't to debate what logo he should wear, or if he should have been elected into the Hall (and personally, if anyone wants to debate that, there's no point. Not only does the guy have Hall of Fame numbers but for the most part he has a Hall of Fame career class-wise. He was a part of baseball history and deserves his election), or to upset Cub fans. This blog isn't to debate whether or not a player should be able to pick his own logo, but to remind everyone that an election into the Hall is an honor. An election into the Hall of fame is a privilege.
- Frank Robinson: Robinson chose to have the Orioles cap displayed on his plaque, although he had played ten seasons with the Reds and six seasons with Baltimore. Robinson won four pennants and two World Series with the Orioles and one pennant with Cincinnati. His second World Series ring came in the 1970 World Series against the Reds. His numbers with the Orioles and the Reds were very good and he won an MVP award while playing for each team.
- Catfish Hunter: When elected to the Hall of Fame in 1987, Hunter declined to choose between the teams for which he played — the A's and Yankees— as he had been successful with both teams and maintained good relations with both teams and their respective owners. His plaque shows him wearing a cap without a logo.
- Nolan Ryan: Born and raised in Texas, Ryan entered the Hall in 1999 wearing a Texas Rangers cap on his plaque, although he spent only five seasons with the Rangers, while having longer and more successful tenures with the Houston Astros (nine seasons, 1980–88 and his record-setting fifth career no-hitter) and California Angels (eight seasons, 1972–79 and the first four of his seven career no-hitters). Ryan's only championship was as a member of the New York Mets in 1969. Ryan finished his career with the Rangers, reaching his 5000th strikeout and 300th win, and throwing the last two of his seven career no-hitters.
- Reggie Jackson: Jackson chose a New York Yankees cap over an Oakland A's cap. As a member of the Kansas City/Oakland A's, Jackson played ten seasons (1967–75, '87), winning three World Series and the 1973 AL MVP Award. During his five years in New York (1977-81), Jackson won two World Series with his crowning achievement occurring during Game 6 of the 1977 World Series, when he hit three home runs on consecutive pitches.
- Carlton Fisk: Fisk went into the hall with a Boston Red Sox cap on his plaque in 2000 despite playing with the Chicago White Sox longer and posting more significant numbers with the White Sox. Fisk's choice of the Red Sox was likely because of his being a New England native, as well as his famous walk-off home run in Game 6 of the 1975 World Series with which he is most associated.
- Dave Winfield: Winfield had spent the most years in his career with the Yankees and had had great success there, but chose to go into the Hall as a Padre due to his feud with Yankees owner George Stienbrenner.