Remember when the Boston Red Sox had arguably the greatest designated hitter of all time?

David Ortiz played a central role in the Red Sox’ success this century. He helped Boston win three World Series titles — 2004, 2007, and 2013. He was elected to the National Baseball Hall of Fame on the first ballot in 2022. And he holds the MLB record for most home runs as a designated hitter; 485 of his 541 career home runs came while serving as a DH.

In March 2016, I interviewed Ortiz at JetBlue Park in Fort Myers, Florida; the interview took place during a promotional event tied to a Mastercard campaign.

Parts of the conversation originally appeared in New England Diamond Digest, a regional baseball publication I co-founded that no longer exists. I retain the rights to the interview.

The original interview contained more than five questions and was specific in part to the 2016 season, his final year. For NewBostonPost’s Five Questions format, I’ve selected three that remain timely — on loyalty, retirement, and the future of Major League Baseball.

What follows are those three questions from the March 29, 2016, conversation.

1. You’ll go down with many records for this Red Sox organization that you’ve played with for such a long time (2003 to 2016) in an era where guys usually don’t stick with one team for long. Why did you stay with Boston?

It's not an easy thing to do, to play for the same organization for a long time. But it all depend on how hard you work, how much you respect the game, how you can show them what kind of leader and player you can be. An organization pays a lot of attention to that, and with this organization, I have been able to get things done all the way around. This is an organization that has been able to appreciate the things I've done around here — and that's the main reason why I stay around.

2. 2016 will be your final MLB season; when did you start to think about retiring?

I've been thinking about it the past couple of years. When you get older in this game, things get to be a little harder to do, you know what I'm saying? Having been blessed with a good career and having thing done my way... And not too many of us get the opportunity for that to happen. This game gives you a lot of things, but at the same time, it take a lot of things away from you. Putting all of that packaged together, at some point, you know it's going to happen, but you don't know when it's going to happen. I guess the moment for everyone to make that decision comes at some point, and, to me, this is the moment.

3. In recent years, there’s been a push to bring Major League Baseball back to Montreal. Is that a city you could see getting a team again if Major League Baseball were to expand? And is there any particular city you’d like to see MLB expand to?

I don't know if Montreal will ever be again a place for a Major League ballclub. It used to be, if you were born for that. It seems like things got out of hand at some point, and that's why they moved the ballclub from there to today, it's the Nationals (Washington, D.C.). I have seen what you say, and I never thought about it, but I have seen baseball being expanded. Last year, there was a couple of teams playing out there in Montreal again, and this year, we're going back, so that might be the idea — to bring baseball back to Montreal — but it depend on the appreciation and how interested people are. That was the biggest issue over there. Nobody was coming to the game.

There's a couple of city out there that I think they should have a major league ballclub. You know when I see a city like San Antonio (Texas), it's a big city. I know they got Houston out there but, New York have two ballclub and Chicago have two ballclub. Why wouldn't they have Houston and then San Antonio, which is not too far away from there? There's a couple more city out there, big city, that have no ballclub, no baseball team, that, yeah? Why not? If the right reason get to be put together, I think baseball should keep on expanding – like it has in the past years.

[Editor's note: When I followed with one word — “Vegas?” — Ortiz laughed.]

Hey! (Points) That might not be a bad idea. It all depend how much you like gambling (laughs). I'm gonna go to watch a series for four game in Vegas and, all of a sudden, man! I ran out of money! (Laughs)

[Editor's note: The Athletics will likely relocate to Las Vegas in 2028.]