After all, both were candidates for the team's managerial opening. When the job went to Showalter, Dempsey expressed his disappointment in no uncertain terms.
So how are things playing out these days in the relationship between the new Baltimore manager and the announcer and former catcher, who is one of the most popular figures in the history of the Orioles?
"Things couldn't be better between Buck and me," said Dempsey. "I have great respect for him. When he got the job, he asked to meet with me in his office -- and we had a great talk.
"Buck said to me, 'They [the Orioles] should have given you the chance to manage a long time ago.' I appreciated that very much."
Dempsey was a catcher for the Orioles for 10-plus seasons and caught more games (1,230) than any player in the team's history. He caught 10 different 20-game winning pitchers and was the Most Valuable Player in the 1983 World Series, when Baltimore defeated Philadelphia. Dempsey posted a .385 batting average in the five-game series.
I have known Dempsey for more than 20 years -- and he has never been afraid to express how he feels. If you don't want a direct answer, don't ask Dempsey for his thoughts.
The media knows Dempsey is a straight shooter and he never will hold back on giving an honest answer. There are times when his candid words will get played to the boldest and most attention-grabbing headlines.
That's why the headlines on Showalter's appointment as the Orioles' manager and Dempsey's reaction to the move drew the likes of: "Dempsey 'very, very disappointed' about not getting job" and "Rick Dempsey: Enough Is Enough."
The key quote from Dempsey, who was passed over for Lee Mazzilli, Sam Perlozzo and Dave Tremble, appeared in the Baltimore Sun: "I think it is probably the biggest mistake made here in a long time, and I'm not talking just today, I mean over the years. Not being given an opportunity to manage this ballclub. Every organization in baseball would like to have someone who has won, who has played in the World Series for the organization, who has learned to manage from 'A' ball up and come back here. I think with the relationship I have had with the fans and this city, I should have been a slam dunk years ago. Someone dropped the ball a long time ago."
The reaction to Dempsey's quotes, particularly in view of the great start by Baltimore under Showalter, hasn't been positive from the standpoint of the longtime Orioles catcher.
"I've been criticized for some of my remarks -- but that's OK because I've got a thick skin," said Dempsey. "I don't think the story reflected the key point I wanted to make.
"The way the story played out, the emphasis was on the selection of Buck -- and it wasn't made clear my point [was] about 'a long time ago.'
"I wanted to prepare myself to be a big league manager and I spent five years as a manager -- including four at the Triple-A level [two with the Dodgers and one with the New York Mets organization].
"This year marked my fourth time I have interviewed to be the manager of the Orioles. I have no problem with the fact that Buck was selected as the manager. I feel that when the previous three managers were selected, I was the best candidate and I didn't get the opportunity."
Dempsey said he believes Showalter will be successful "because he pays attention to every detail that goes into managing a team."
Dempsey said he respects Showalter, in that he feels the veteran manager is a straight shooter "who will say it like it is," adding "we're very much along the same lines when it comes to being candid with the players and the media.
"The thing Buck and I now have in common is that we want more than anything to see the Orioles succeed," said Dempsey. "I know Buck also has talked about bringing some of the former Orioles back closer to the team -- and I think this is great."
Dempsey makes no excuses, nor should he, for wanting to manage the Orioles after serving the team as a player, coach and now an announcer ... and would be happy to help Showalter and the Orioles in any way he can, as always.
Rick Dempsey remembers first-hand what it was like to be a part of the Orioles when they were winning a World Series.
It's a feeling, Dempsey says, that he would like to experience once again.
Fred Claire was a member of the Los Angeles Dodgers from 1969-98, serving the team as Executive Vice-President and general manager. He is the author of "Fred Claire: My 30 Years in Dodger Blue." This story was not subject to the approval of Major League Baseball or its clubs.