Interview with Bobby Sylvester,
St. Louis Apostles

BIGGEST DADDY: Hello, Mr. Sylvester! It's great to have you here. So many changes with you since the last time we chatted in 2006. For example, the last time, your franchise was the Wapakoneta Hippos! But in all seriousness, you are getting married and having kids....Tell us a little bit about what's been going on with your life lately!

Bobby Sylvester: Thanks for having me on, Big Daddy. Reading back through those old interviews makes me cringe—amazing what 10 years can do to a guy—likewise, I’ll probably feel the same about this interview in 2026.

I’ve been married for 4 years now—-doesn’t that make you all feel old? We have an 18 month boy, Soren, who is tall southpaw with a blazing fastball, and another boy on the way (my wife was actually due 3 days ago). When asked to give his brother’s baseball scouting report, Soren proudly exclaimed, “Black hair, baseball bat, hurry hurry”. Hard to tell exactly what that means, but Soren was quite emphatic, so I think the future is promising. I know a lot of younger parents hate what having kids does to their social lives, but the truth is, we knew what we were getting into, and we decided to do it because we wanted it. I have similar sentiments in regards to marriage—all the sitcoms paint it as a miserable complex, but it is so much better than running around in a bachelor pack. This is the greatest time of my life so far, and we are looking forward to adding a couple more kids in a few years.


BD: What do you do for a living? And how do you like it?

BS: I am an Instructional Technologist for a public school district near St. Louis. Basically, I teach teachers and administrators how to utilize newer technology (iPads, Chromebooks, Promethean Boards), and train them to use various software to maximize their job efficiency. The town is a mirror image of Ferguson, so there are certain challenges, but the job is very family friendly, which is the most important quality to me. I never leave later than 4:10, never take work home, and am never stressed—my boss is great, and I share an office with one of my good friends from college, who happens to share a passion for theology, cardinals baseball, and tea party politics. I am not actively looking for a job, because I doubt the grass is greener on the other side.


BD: What's the best part about being a young dad? What's the hardest part?

BS: The best part is being able to share something so significant with my wife. Seeing her in her element has given me a much stronger appreciation for her, and it is a blast to work together with her on something so challenging. The hardest part is leaving for work everyday. I would love nothing more than to spend every second with them—I don’t want to miss anything.


BD: Now, let's see what's going on with your team! Oh. 20 games below .500, after two previous years below .500. What do you have to say about the state of your franchise right now?

BS: The manager is lousy. Our team should be performing much better this season, but as I’ve previously stated—sometimes a roster plays over their head and sometimes they underperform—not too much you can do about it. I’ll try to take this year’s beating in stride and put out a contender again next season. The last two years I made no apologies for rebuilding—sometimes you have to (in the Eck League). I have been trying to transition to a spot where I don’t trade much, and my roster is finally in a place where the only moves I want to make are when I have too many players at one position and am dealing from excess.


BD: Who are the right guys on your squad to build around? Or will you trade anybody?

BS: I can’t trade anyone away, but do want to move 2 farm guys for 1 this chapter to open up room to grab 1B at bats. I don’t want to drop anyone on my roster. As for guys to build around, I’ll give you a list of our 10 most important players over the next 5 years (Baseball America style):

1)JD Martinez
2)Michael Wacha
3)Yasiel Puig
4)Jorge Soler
5)Carlos Martinez
6)Anthony Rendon
7)Lucas Giolito
8)Carlos Rodon
9)Yasmani Tomas
10)Jake Odorizzi

BD: You like to make trades, it seems -- do you ever overthink these trades? Do you have any regrets?

BS: I have made way too many trades to not have regrets. My most recent one is Miguel Sano—idiot. Others that quickly come to mind: Joc Pederson for Wilmer Flores…Jose Altuve for Michael Matuella and Kenta Maedea…Pujols for Kenley Jansen…absorbed 30 million dollars and dealt two top prospects for Oscar Taveras…Jorge Soler for Castellenos, because I then had to trade a ton to get Soler back. I could write a book about all the bad trades I made. No, I don’t think I have ever under-thought a trade. It is a curse that I have to think about something from every angle before proceeding.


BD: On the other hand, which one or two trades are you most proud of?

BS: Man, this a tough question because every time I big-time win a trade, I feel really bad about it. I feel like I owe Ryan the moon since I dealt Moustakas to him for 100k Mike Minor, 100k Matt Carpenter, 100k Brandon Moss, 100k Jose Altuve, 100k Leonys Martin, and 8 mil in cap space. That was more of a “looks much better in hindsight” kind of deal. The ones that I take pride in are the ones where a GM realllllly doesn’t want to trade a guy, so I big-time over pay to make sure I get the guy—then the hunch turns out to be correct. My moves to get Giolito, Wacha, and Rendon come to mind. I am also still really happy with the Buxton for Carlos Martinez (and two other good prospects) trade, although I wish I would taken Glasnow instead of Jorge Alfaro.


BD: What songs are included on the soundtrack to your life?

BS: Here is a CD worth:
1) Eddie Vedder - Guaranteed
2) Matchbook Romance - Back to Good
3) Avett Brothers - January Wedding
4) Ace Enders - Timshel
5) Elliott Smith - Angeles
6) Vertical Horizon - Everything You Want
7) Brandon Heath - When I’m Alone
8) Rocket Summer - Goodbye Waves and Driveways
9) Rookie of The Year - Blue Roses
10) The Wedding - I-540
11) The Starting Line - Best of Me
12) The Early November - Sunday Drive
13) The Ataris - In This Diary
14) Yellowcard - Empty Apartment
15) Straylight Run - Existentialism on Prom Night
16) Matchbook Romance - If All Else Fails
17) The Maine - Into Your Arms
18) Lecrea - Truth
19) Alan Jackson - Livin on Love
20) Dashboard Confessional - For you to Notice
—My go to Pandora Stations are Matchbox 20, Matchbook Romance, George Strait, and the Avett Brothers.


BD: What story does your family always tell about you?

BS: I have no idea what my sister or parents like to tell, but my wife always brings up a time when we were dating. I just bought one of those gallon tubs of Cookies and Cream Ice Cream (because I was a poor college student) and a storm knocked my power out late at night. I didn’t want it to melt so I took it to her parent’s place, but there was no room in the freezer. I did what any man would do—I ate the whole thing. None was wasted. Now that wouldn’t be so bad, except for the fact that I left my lactate pills in my apartment and have a mild lactose intolerance. A bad night ensued.


BD: What do you put on your sandwich?

BS: I don’t eat sandwiches much—I’m a big burrito guy…I love to cook and have four go-to burritos that I like to make:

1)Couscous, duck breast, cucumbers, and a mix of asian seasoning
2)Meatballs, homemade tomato sauce from my home-garden, provolone cheese, and Pepper Plant salsa (the best)
3)My wife makes carne asada about once a week. Carne asada steak, yellow bell peppers, crinkle cut french fries, sour creme, and green chili
4)Vanilla beef, homemade soft-vanilla chips, corn, dave’s insanity sauce, and chili


BD: It's date night! Where are you and your wife headed?

BS: Usually Busch Stadium for a Cardinals game. If going out to eat we will usually go to an Asian Fusion place called Wang Gang. We aren’t really date people—When we have spare time we usually both read or she prefers to stay home and write while I work on my board games.


BD: What will prevent the Cardinals from winning the World Series in 2015?

BS: Many things. The formatting of the playoffs doesn’t make much sense to me—The Phillies could beat the Cardinals in a 7 game series—it is just too short of a series and can lead to anything happening. If they aren’t hot at the right time then they won’t win—period. If you are asking what our problems are: Four pitchers in our bullpen have already appeared in 40+ games. Rosenthal has a tight shoulder, and Walden won’t be the same when he returns. I am worried about the pen later in the season, and don’t have any confidence in Jaime Garcia lasting the whole season—also Tsunami and Wacha haven’t thrown a ton of innings, so I am not sure how they will last into the playoffs. Our lineup is middle of the pack, but the season doesn’t depend on them—it is all about the pitching and if they are healthy. If I had to guess, I’d say the Pirates over take us for the division and home field advantage and that we get to host the Cubbies in a playoff game.


BD: You have some strong opinions on the BDBL board around how good or bad a young player will be. Is there any exaggeration with those?

BS: I have strong opinions about everything, if you haven’t noticed. I probably exaggerate here and there, but it definitely hasn’t been a rule of thumb. I eat crow fairly often, but I will put my forecasting skills up in competition against anyone in the league—any takers?


BD: What's your favorite part of the BDBL?

BS: The people. No other internet based league gets together once per year, has pages of political discussion, has each other’s phone numbers, and are genuine friends. That is what separates this league from everything else.


BD: When's your next big trade?

BS: When is the next farm draft? Just kidding. I will probably be dealing a few of my 80 starting pitchers and 15 cuban outfielders this off-season. With all the young guys I have collected, there isn’t much turnover on my roster via free-agency or retirement so I am running out of roster spots—it will likely be a 3 for 1 or 5 for 2 type of deal, and it will almost certainly involve a guy I really believe in—-I don’t deal via trade block very often—usually all of my moves are a result of me targeting specific guys and doing what it takes to get them. To give a sneak preview, I am really really high on Noah Syndergaard, Rafael Devers, Alex Reyes, Jake Thompson, Sean Manaea, and MAKEIL FRANCO, who I have been trying to overpay for going on several years now.


BD: Thanks!

BS: It was fun—thanks for asking me!