The offseason is a time for a player to enjoy a break from the grind of a professional season. Although players love the game, they also know that being so focused is taxing. You are away from family, you miss major events in their lives and you barely have time for everyday life. It is a sacrifice worth making for that goal of building a major league legacy but it comes at a price.

Yet each off-season represents a different moment in time for a player. As they age, this time changes purpose and so do the stages of their career.

In this journal, I want to walk you through the many offseasons of my career to help share what it is like for these Cubs players, or any player, when they step away from the game, expecting to return. Each entry will be a different time stamp, mostly in chronological order of my career. You will read about these events during different off-seasons.

Winter Ball
Free Agency
Loss - My father passed away one off-season
Being Traded
Should I Retire?
Should I Un-Retire?
The Multi-Year Deal
Getting Cut
New Workout

And more....

I hope you will find that these stories capture the emotions of a player's career at a time when they are farthest from it. And maybe, this will help with the waiting until the spring comes around and baseball is here once again!



According to, the 2018 Cubs organization currently features 19 players who are playing winter ball, from the Arizona Fall league to players heading home in Latin America to play in their home countries. This is a standard offseason practice, with varying goals as to what each player is trying to accomplish. In my case, the Arizona Fall League after a season in Double-A became a marker.

I knew that if I could hold my own with the top prospects in minor league baseball, I believed it meant that development from that point would lead to a big-league promotion one day. But I had to put up the numbers. The Fall league would prove to be a watershed moment for me, with a .299 batting average and a player of the week award. Our team lost in the finals, but I had gained a needed boost of confidence that I could play with the best.

Cubs’ top draft pick Nico Hoerner is proving just that, not just to the brass that selected him, but to himself. A .338 batting average against the best of the best is a great start to his career. It may be under the radar to the world, but the Cubs front office is taking notes, as are all the scouts attending these games.

My winter ball experience only began in the Arizona Fall League. It continued in a last-minute roster move by the Cubs director of instruction, Tom Gamboa, while I was training in the Cubs Instructional league one off-season. Gamboa saw that my Triple-A stat line did not match the ability he heard about and now was seeing, so in a leap of faith, he jump-started my flatlining career with an opportunity to play in Puerto Rico for his team in Mayaguez.

But he reminded me that this was not just fun and games. “This is not just development, we are playing to win,” he told me. Although I was working on taking more pitches and being a better base stealer, we also needed to win. It may have been winter ball for me, but in Puerto Rico, it was their main season. Money was paid, stadiums were filling, and fans expected good baseball, not just someone working on his curveball.

I also knew that this was the fork in the road for my career. I was 25. I was a Triple-A player, working out in instructional league with some 18-to-20-year olds (including Kerry Wood, who was newly drafted). I was running out of chances and I needed this winter ball to go well, exceptionally well. Despite my tension with my manager in Iowa, there would be no cover for how I performed in Puerto Rico.

It would turn out that Puerto Rico was where I broke through. I felt completely at home with the culture and the people. My father was of Caribbean descent and it felt like I belonged and the people treated me like family.


Before I even played one game there, I knew I had gained a support system that would only aid my development. It made me understand how difficult it must be for players who are from the Dominican or Venezuela, venturing out for the first time in the United States with language barriers and cultural adjustments to make before they pick up a ball. It is stressful to perform, let alone to do so in a foreign place.

Puerto Rico was not so foreign to me, being a commonwealth of the US, but it was a change. Cold showers, an apartment with little hot water, no AC, no phone or TV. To some degree I chose that, in the spirit of Kris Bryant, who celebrates being uncomfortable as a way to gain focus. To inspire and motivate through scarcity, given the incentive to work your way out of a tough space.

In the end, the simplicity of how I chose to live in Puerto Rico (and I had an option to live in a resort that I rejected) was the best choice I made. Baseball was the focal point and it paid off.

Two years in Puerto Rico yielded the best I could have hoped for in that time. I walked away with an MVP trophy that first year (beating out Roberto Alomar in the vote), led the league in hits, two All-Star appearances and the top team prize, winning the championship in year two. One year we knocked off the San Juan team that had many members of the Puerto Rican Dream Team, which had included Roberto Alomar, Juan Gonzalez, Edgar Martinez, Bernie Williams, Carlos Delgado, Carlos Baerga, and Hector Villanueva, to name a few.

There are experiences in baseball that are non-linear in nature. On paper, professional baseball is just a progression. You go from the draft to A-ball to AA-ball, to AAA-ball to the show. We think that is it. Straightforward. Yet it is full of unpredictability.

You need a sponsor, you need a shot of confidence no matter how high a pick you were, you need to stay healthy, you need to step outside your comfort zone to deal with adversity in a game that, figuratively and literally, throws you curveballs all the time.

I would return to the mainland United States, feeling a mix of accomplishment, hope, vindication and drive. I calculated that since the beginning of spring training two years prior to the completion of my Puerto Rico run, I had been involved in nearly 500 games (spring training, regular season, winter ball, playoffs, repeat). I finally felt like I was delivering on my first-round pick pedigree after some tough years.

On my return, I would be greeted by Ed Lynch, the GM of the Cubs. In one meeting, he planted a small reminder of the work still to be done. Although my success in Puerto Rico was an accomplishment, he challenged, “now, let’s see if you can do it in championship season here.” A sobering reminder of how baseball is a game of todays. Good work, nice trophy, now do it again.


Winter ball, for me, was transformational. Not only did it change my game, but it changed me. All of the things that do not appear in the stat column mattered. I made lifelong friends (my manager in Puerto Rico, Tom Gamboa, spoke at my wedding), I have a goddaughter in Puerto Rico, I had a broken heart from the hurricanes that devastated the island, knowing nearly every inch of it from driving every other day to games for two full off-seasons.

Many years after our championship season, I returned with a friend to a game in my team’s stadium. It was like I never left. The warmth, the welcome. And even more powerful was the time after that, 20 years after my last game there, when I ran into a security guard at the mall that used to drive with me and my teammate to games when he was 18. Time stopped, and we recognized each other, instantly. I have so much love for my time there.

While we review the top news of the major league team, Addison Russell, Theo Epstein, Cole Hamels, luxury taxes, and hitting coaches, let’s remember that there are a handful of players perfecting their craft, many far away from home. They are just trying to get better, so they are the best they can be, when and if the opportunity knocks on their door.

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