Jon Searles is unique. Originally an eighth-round pick by Pittsburgh in 1999, Searles attended Penn while pitching in the Pirates, Expos, and Cubs organizations, earning a finance degree from the Wharton School of Business when he wasn’t on the mound. Now, after his fourth consecutive season in Double-A, his career is at a crossroads. David talked to Searles about where his career has been, where he sees it going, and how he views the game on both a personal and a business level.

David Laurila
: When I interviewed you two years ago, you were 25 years old and in Double-A with the Red Sox. What has happened in your life since that time?

Jon Searles: After winning the Eastern League championship with Portland in 2006, I became a free agent for the second year. I returned home to Long Island, where I was able to land an internship with a commercial real estate firm in Manhattan for a few months over that winter. It was a nice change of pace for me, and a very interesting field to be involved in; I really enjoyed knowing that I was able to meet a challenge in a different field and take advantage of my proximity to New York City. Of course, I continued to train for the upcoming baseball season. The days were busy, but that’s how I enjoy things. I signed a free agent contract with the San Diego Padres that winter. I made the Double-A team in San Antonio after one of my better spring training camps. Crazily enough, our team won the Texas League championship in 2007, giving me back-to-back Double-A rings. I actually have two A-ball rings with the Pirates as well, giving me four total. This offseason I’ve been home again, and doing some coaching. I signed a contract with the Long Island Ducks of the Atlantic League. The stadium is 20 minutes from my house and I will be in the starting rotation. I’m very excited about having all of my family and friends see me play, as not many got a chance to get to San Antonio last year. I hope to get off to a good start and sign with a team looking for some help in the minor leagues early in the season.

DL: What are your expectations of independent league ball? How do you think it will differ from affiliated baseball?

JS: From what I’ve heard, the Atlantic League is a very good league with plenty of talent. In particular, the Long Island Ducks are known to bring in plenty of talent with professional experience at the Double-A, Triple-A, and even major league level. I’ve talked to a number of guys who have played indie ball, and many of them said it’s a chance to really get back to the reason we all started playing, because we love the game and we are pretty good at playing it. I expect the atmosphere to be a little more laid-back with regard to practices, pre-game routines, and many of the off-the-field policies that affiliated ball has. I think the biggest difference may be some of the outlooks by the players, but I won’t know for sure until I get there. In the minor leagues, guys are teammates for a number of seasons and are working towards a goal of making the major leagues with their current team and their current teammates. In the indie leagues, you may have a major league veteran playing alongside an A-ball player. Obviously, the outlook on the game, both future and past, will differ between these two players for numerous reasons. In the end, though, both still get a rush out of taking the field.

DL: The vast majority of players in the minor leagues never make it to the majors. From your experience, how many guys admit that their chances are slim–either in private conversations or more openly?

JS: I guess it may be the big elephant in the corner that nobody will admit is there, though it only feels that way at certain times. As you get older and play at higher levels you realize just how few guys make it and how brutal the process can be. By the time you reach the upper levels of the minor leagues you’ve seen countless teammates and friends get released, retire, fall to injury, and so on. I never got used to it, but I understand it’s part of the game. When you are young and first drafted, everyone sees themselves playing in the big leagues with the team that drafted them, playing alongside their current rookie-ball teammates. When you see that first teammate get released and have to look them in the eye and shake their hand as they pack their equipment bags, things become very real very quickly.

Players who are secure in themselves and their ability can talk openly about the chances to get to the major leagues. We understand the numbers involved and just how few spots there really are. I’d say the topic is really only brought up a few times a year, like in spring training when there are numerous cuts all around you, and during a rough patch of such a long season, maybe on a eight-hour bus trip in the middle of nowhere among some very close teammates. But those are the type of things that build character.

I don’t want to paint such a rough picture, though. I’ve had the best time of my life playing in the minor leagues. I know the percentages aren’t in my favor, but they aren’t in anyone else’s favor either, so we all have a shot. It is what it is. This is an attitude that is developed over the years and by learning what the game teaches you. I wouldn’t have been able to give you that answer after my first year in rookie ball.

DL: The Padres were your fifth organization. What were the differences in how each organization operated?

JS: Each organization is fundamentally the same. The game has been played for so long now that people realize there is a right way and a wrong way to play. All organizations teach the right way–some may just use different terminology or have different philosophies on how to play the right way. Some organizations may focus on first-pitch strikes, while others will stress throwing two of the first three pitches for a strike. Either way, the idea is to get yourself in a pitcher’s count so that you can attack the hitter with your out pitch. Hitting philosophies may be different, but I wouldn’t really know. Sometimes I can tell when I pitch against certain teams. If you see the batter shorten up on his swing with two strikes and try to hit the ball on the ground, you know the organization is trying to make contact and force the defense to make a play. Other times you will see guys take a huge rip at a two-strike pitch and punch out. Obviously those hitters are told to try and develop their power potential and not to worry about the strikeout. The minor leagues are about development. Each player needs to develop their own tools, and I think it’s up to the organization to try and help them do that while finding guys who fit the overall system’s approach.

DL: Having grown up in New York, what was it like to spend the 2006 season in the Red Sox organization? The easy answer to the question is that childhood allegiances go out the window once you sign a contract, but is it truly that simple?

JS: You know what, I took a lot of heat for signing with Boston from people back home, but none of it was that serious. I think people who really know the game understand that it’s such a privilege to be able to sign a professional contract, and as players we have to take advantage of every opportunity. For me, I grew up going to a lot of Mets games. Shea Stadium is in Queens, so it was an easy trip for us to get in and out from Long Island. I was actually a Cubs fan growing up. I loved listening to Harry Carey announce the games. For me, it really was pretty simple to let the fan inside of me go and start to play. I’m a fan of the game first and foremost. As long as I have a uniform on and they give me the ball, I’m all set.

DL: Two years ago you said you’d love to be a GM, or maybe even an owner, someday. Is that still a career goal?

JS: I think some sort of front office position is a goal of mine. I’m interested in seeing the inner workings of a team and how it all comes together. I’m also interested to see how my years of experience in professional baseball combined with my degree from Penn would work for me. I try to learn from any situation I’ve been in and I feel I have some unique ones. I think I could be an asset to a team, but that’s to be determined down the line.

DL: You have a Finance degree from an Ivy League school. How do you view the business of baseball, from the labor contract to the relationship between the owners and the players to how the game is marketed?

JS: I don’t know the specifics of the labor contract, nor do I really know how the players and owners interact at the major league level. I will say this though: I may be partial. On a basic level, major league baseball, or baseball in general, is a product that is marketed and sold to the public much like anything else. That being said, it is a great product that millions of people enjoy and that really only has a few competitors–the NFL, NBA, and NHL. In order to produce the best product, teams must draft, develop, and sign the best players to put on the field each night. I think all teams are doing a great job with regard to this. You can see all the investments in the minor league players, facilities, training academies, and so on. Also, teams are busy year-round trying to sign the best free agents to remain competitive. Without the best players taking the field, the quality of the product would suffer. In a way, the players then have a certain amount of leverage. In order to offset that leverage, the organizations understand that they must develop as many major league-caliber players as possible. Increase the supply to meet the demand.

The playoffs are a great example of how well the game is marketed. Nobody wants to miss a playoff game when they are on TV. I think the marketing during the regular season is more in the hands of the teams and their regional markets. It’s important to build that loyal regional fan base, so that when the postseason comes around people really are pulling for their team.

DL: When Alan Schwarz of the New York Times wrote about Randy Newsom and Real Sports Investments last month, you were one of the people he quoted. Can you give us a more detailed look at how you view RSI, both from the perspective of a player and as a Wharton grad?

JS: I think RSI is a great concept and very innovative. As with any new idea, it’s open to discussion and criticism from people who hear about it. Rather than immediately dismiss the idea, I think those who developed it should be commended on their ability to think outside of the box and take a shot. That’s how progress is made.

As a pure investment opportunity, I’m not sure if the concept would work without some fine-tuning. Obviously a first-round draft pick who is a lock for the major leagues would not commit future earnings for the same up-front sum as readily as a fringe minor league role player. It is analogous to the stock market’s pricing of prospering companies versus those companies that have the potential to one day operate effectively, but are right now very much unheard of. In order to accurately price the up-front sum of money required to offer a top prospect in exchange for a percentage of future earnings, all information regarding this player must be available to the investor. This would require organizations to reveal their scouting reports on players as well as plans for current major league players regarding trades, contract extensions and when they plan to call the minor leaguer up to take the veteran’s spot for example, among many others. Teams would never offer this information in my opinion, for too many reasons to list.

As a chance for the fan to have a reason to follow the career of a minor league player, I think it’s pretty cool. Imagine a Triple-A player throws a complete-game shutout one night, then sticks around to sign a few autographs for a group of young kids who came to watch with their Little League team. Those kids are hooked on the game and they may even have a new favorite player. But maybe the coach sees something he likes in the player and has a few extra dollars to invest. He does so in the player because he likes what he saw and takes a chance on him. Now he has even more of a reason to watch and follow the player and all levels of professional baseball. The game has a few more fans.

DL: With baseball being both a business and a time-consuming job, do you think players tend to lose touch with what it means to be a true fan of the game?

JS: I think as players we focus on baseball in a different way than the fan might. It is a job, and while I couldn’t think of anything better to do with my life than be a major league baseball player, that requires an enormous amount of time, energy and dedication. That doesn’t mean that players are not true fans of the game. I love watching games on TV when I have the chance. But I think that players watch and appreciate different aspects of the game than the fans might. It’s almost like we are studying the game rather than just enjoying watching the ball get hit really far. I want to see what pitch they throw in what count to certain hitters; I watch the catcher’s signs with a runner on second and try to figure out the sequence they use.

The definition of a true fan is subjective. I know I am not a die-hard fan for any one team. When people find that out, they seem really surprised, as if I don’t care about the game. I can tell you that baseball has been, and always will be, a very special part of my life. It’s just that, after experiencing so much of what goes into it on and off the field, I pay attention to other details. It’s hard to explain, but it really shows up when I watch games with friends and family once my season is over. But we are all fans of the game, and we can’t shut off the TV until the last out is made.

Thank you for reading

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