The Next Chapter

When Kevin Pillar’s playing career is complete, he’ll have at least nine major league teams on his resume. After an extended early run with the Toronto Blue Jays, he’s logged time with eight of those clubs since 2019. With each stop along the way, he’s learned that a diligent work ethic and a team-first mindset can lead to employment opportunities, even when the job market is a bit daunting for players in their 30s.

“He’s the ultimate true professional that every team should have,’’ said Angels third base coach Eric Young. “He goes about his business in the right way. He doesn’t take a day off. He understands his role and what he brings to the team, and he’s always doing something to help you win. It’s a joy to watch him play. He always -- always -- goes all out.’’

It’s been a chaotic season for Pillar, who signed with the White Sox in February and hooked on with the Los Angeles Angels after being designated for assignment by Chicago in late April. He recorded his 1,000th career hit in May and achieved another personal goal when he reached 10 years of major league service in July.

Pillar’s Baseball-reference.com profile still lists his nickname as “Superman,’’ the moniker he picked up as a young, fence-scaling outfielder in Toronto. He won the Wilson Defensive Player of the Year Award as baseball’s best center fielder in 2015 and was a three-time Gold Glove finalist, but missed out each year at a time when Kevin Kiermaier, Jackie Bradley Jr., Mike Trout and Byron Buxton made for a crowded field of candidates at his position.  

As Pillar embraces the possibility that the end is in sight, he’s in a pensive mood. He recently looked forward to the opportunities that await and reflected on the rewards and challenges of life in the majors in a conversation with the MLBPA.

You told USA Today in July that you were “98% sure’’ in your heart that this season will be your last. Where does that stand?

I’m definitely prepared for it to be the end. Coming out and saying that was kind of my way to remind myself to enjoy what could be my last year.

My wife and I have our 10-year anniversary in October and my daughter turns seven. After the season, we're going to go to Costa Rica just to get away as a family. Hopefully I’ll leave there with some clarity of what's next for me and my future -- for our future. It won't be just my decision. It will be a decision that my wife and my kids will help me make, and we’ll make the best decision for our family.

If an opportunity (to play) presents itself sooner rather than later, that’s a decision you’re going to have to make. But I won’t go until February.

A lot of players go through an emotional tug of war in anticipation of this transition. Has that been the case for you?

I’ve talked to a lot of people in this game who say, ‘If they’re going to pay you to keep playing, keep going.’ Then I have this other side that says, ‘I'm content. I'm happy with what I’ve accomplished.’ Financially, I'm in a good place. We've made enough (money) where I can stop playing baseball and just be a full-time dad and pursue other hobbies and passions of mine.

You and your wife, Amanda, have two children, (daughter Kobie, 6, and son Jet, 4). How does family factor into the equation?

A lot of kids go to school in their neighborhood and they’re in their house and they get to play with all their friends all summer. We made a decision collectively to be together as a family this year. I asked my kids to pick up and come to Chicago and Anaheim, and we decided to home school them for the time being. They don’t get that normalcy that a lot of kids get.

They’re at an age now where they think what I do is pretty cool. They other kids will say to Jet, ‘Hey, your dad's Superman.’ And he's like, ‘No he's not. He doesn't wear a costume. That's just my dad.’ That part's obviously the best.

My kids both like watching the game and having me throw them balls in the backyard. My son loves baseball. He’s always swinging a bat. So that kind of pulls on the heartstrings for me to keep playing, because I know as they get older, they're going to remember more. But I also want to be able to coach my son when he’s five in his baseball league. That's why the decision is never going to be easy.

How much of a challenge does life on the road pose to a ballplayer’s family life?

I mean, you miss birthdays and first days of school. This year I was pretty fortunate to have spring training in Arizona, so I got to see their first day of school. They both played softball and tee-ball, so I was able to be a part of that. But typically, I've never been a part of that. Four or five years ago, I missed my son taking his first steps because I was on a road trip. There are pivotal moments of their development and their life, and you're not always around.

But the tradeoff is definitely worth it. I'm living my dream. My family is in a good place because of my hard work and perseverance and me wanting to do this. We've been blessed with this. When my daughter was a year old, I got to play on the Japan All-Star trip and we got to experience that. Baseball has provided my family with a lot of opportunities.

What did reaching 10 years in the big leagues signify to you?

It was emotional. It was humbling. It was exciting. Like my former teammate Josh Donaldson said, ‘This is a get it done league.’ You can trick your organization and get lucky for a year or two, but it's hard to do that for 10 years. You can't trick people for 10 years. You can't get lucky for 10 years.

When David Ross was in his final go-round with the Cubs in 2016, he made it a point to eat a cheesesteak in Philadelphia, pay a visit to the St. Louis Arch, and put together a bucket list of items in different cities. Have you done anything like that?

As a major league player, you have the ability to travel around the country to these different cities and see a lot of iconic things. I've done mostly everything there is to do. In New York, I've done the 911 Museum and been to the Statue of Liberty. I've seen shows on Broadway. In Chicago, I’ve done the architectural tours and all the sightseeing things. I’ve seen the Liberty Bell and taken my wife and kids to the Rocky steps (in Philadelphia). 

A lot of it was intentional along the way. I just wanted to make sure that I was maxing out my big league experience. I wouldn't say there’s much left to check off. I haven’t homered in a handful of major league stadiums, but I’m blessed to say I’ve played in every stadium there is now.

You won a Fielding Bible Award, the Wilson Defensive Player of the Year Award for center field in 2015 and the Willie Mac Award as the most inspirational San Francisco Giant in 2019. Do any individual achievements from your career stand out in your mind?

The Wilson award is something I take a lot of pride in. The Willie Mac Award was voted on by my teammates at the time, and awards that come from your peers are always really special.

Making an All-Star team or winning the Gold Glove would have been at the top individually. But a lot of those things are out of my control. Would it be nice to go home one day and have a Gold Glove sitting in the middle of a game room or my office? Sure. But it wasn't from a lack of effort or preparation or trying. That's just the way the chips fell. At the height of my defensive career, I ran into some guys that were equally as elite. If I had played two years earlier or maybe three years later, I might have had a couple of those things.

Have you thought about how different it will be to not have to prepare for a game every day?

Baseball has been my life since I was four years old. Really, since I was in college, it's been my full-time obsession and year-round job. Once I can kind of push that aside and focus on other things, I'm excited to see how that turns out.

I'm excited when that's done, and I don't have to worry about taking care of my body, making sure my arm is good, my hamstrings are good. Is my swing right? Is my body loose? And I’ll actually have the time and energy to spend on some other stuff. I'm curious to see how the commitment and hard work and dedication that I’ve put into my sport will apply to other aspects of life.

What are some non-baseball pursuits you see yourself gravitating toward?

I just bought a 17-acre ranch in Texas. That's where we're moving. So I’m going to get pretty heavily involved in that -- raising cattle, goats, cows and chickens. We have a couple of llamas on the property. I want to spend a little more time fishing in the pond that we have and immersing myself in hunting culture. I’ve done it a couple of times and I’ve always been very interested in that.

I’ve done some real estate investing and some house flipping. I bought a couple of rental properties, and they kind of run themselves. When a check's not coming in anymore from baseball, and push comes to shove and I need to make money for my family, I'm excited to focus my time and energy on something else when I don’t have to worry about performing on the field.

Do you have any interest in the standard routes of coaching or broadcasting?

If you asked me four or five years ago, I would have been 100 percent, ‘Let’s do TV.’ Now I'm a little bit more interested in the coaching side, even though I don't want to be in the dugout full-time. Front office stuff intrigues me, too.

I still have some thoughts and ideas in terms of content or TV shows coming from (the viewpoint of) a current or former ballplayer. These are things I think about when I get up in the morning or before I go to bed at night, when I'm not thinking about my job.

You’ve played for nine franchises. What are some connections you’ve made that you expect to continue once you’re done playing?

As much as I wanted to stay in Toronto and be a Blue Jay my whole career, I realize now how many people I’ve gotten to share a locker room with and become friends with. I’ve got guys from the Giants like Brandon Crawford and Evan Longoria that I still talk to all the time. There are guys from my Toronto days, like Justin Smoak. Devon Travis, Jose Bautista and Ryan Goins. You come across certain people along the way and it's more than being a teammate. You share a bond and think alike. I'm fortunate to say that I’ve made a lot of really good friends in this game that I still talk to religiously.