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Diamond Challenge: How I fell in love with Fantasy Baseball

CDM Sports' Diamond Challenge (DC) is accurately described as the granddaddy of all fantasy sports games. It is the oldest fantasy baseball salary cap challenge, paying out league, division and overall winners of their game for over 20 years. I first played DC in 2003, a couple of years out of college.

Though I had been transcribing box scores and baseball card stats since the age of 14 and playing in draft leagues since 17, playing DC for the first time unearthed my deep passion for fantasy baseball. I was introduced to the contest by college buddy and baseball savant, Steve Zacks. He explained the setup and asked if I wanted to share a team for that 2003 season. I bought in, and in no time, I was hooked.

Steve and I worked well together and kept each other in check, and from making rash decisions. Our offense was supported by the likes of Manny Ramirez, Albert Pujols, and Todd Helton – who hit over .400 for us in 400-plus at-bats. The staff was powered by Brandon Webb, Jason Schmidt, and a dirt cheap Mark Prior. Midway through the season, we added slugger Jose Guillen after he was traded to the A's, and we shot up the standings – first in our league of 25 contestants, first in the division of 250, and sitting in the top five overall out of over 8,000 teams in early August.

As part of DC, every team manager gets 16 player purchases to start the season with. Player purchases were golden tickets and needed to be used wisely and with prescient timing. In desperate need of a cheap arm down the stretch, Steve and I decided to use our last player purchase on Dontrelle Willis over the Twins' Venezuelan pitching prospect and recent call-up, Johan Santana.

You can probably guess what happened.

Willis ended up getting bombed for 10 earned runs on August 11, 2003, while Santana barely allowed more than an earned run per start for the duration of the season. That one mistake cost us first overall and a split of over $30,000 – a huge haul for a couple of fantasy geeks just dipping their toes into the real world. We ended up winning our league and division, and finished fourth overall.

I've played DC every year since. No matter how many NFBC teams or other leagues I'm in, I've always treated the day that DC salaries came out as if it were Christmas Day. I know many who share that sentiment. The DC message board – known as the BBS – is where I met some of the smartest guys in the game. Our version of the the PayPal Mafia, if you will.

Author and Two-time DC champ, Larry Schechter, wrote a chapter on Diamond Challenge strategy in his book, Winning Fantasy Baseball. Chad Schroeder, and NFBC Hall of Famers Lindy Hinkelman and Stephen Jupinka, three of the world's top-ranked players played DC for many years. They gathered much of their strategies for success for what came later for them in the NFBC. Another NFBC overall champ and two-time FanDuel millionaire Dave Potts played DC for a few years as well. Even current Yankees' assistant GM and Director of Quantitative Analytics Michael Fishman was a perennial league winner and a regular on the BBS.

At the turn of the century, the Diamond Challenge was a flourishing venture. Full-page ads across newsstands everywhere in USA Today, with over 10,000 contestants annually. Grand prizes of $50,000 were unheard of in our industry, but CDM paid them out promptly, year after year.

CDM has gone through much ownership change over the last decade, but are likely most well known for their groundbreaking victory in an intellectual property lawsuit in 2005. With compelling support from the Fantasy Sports Trade Association, a district court judge ruled in favor of CDM's parent company. The ruling declared that 'statistics are part of the public domain, and can be used at no cost by fantasy companies'. That these statistics were not a violation of professional athlete's rights, as was claimed by MLBAM and MLBPA. The decision was a huge victory for the fantasy sports industry. That ruling from 2005 has most recently been cited in defense of Daily Fantasy Sports companies who are currently under much state government attention as they move closer towards statewide legalization and regulation in that space.

In fact, the basic premise of Diamond Challenge is the standard blueprint that companies like DraftKings and FanDuel use today. Picking players per position, under a set salary cap, while being mindful of percentages at which these players are owned. One of CDM's past owners, Fanball, actually developed the first version of DFS – a game known as SnapDraft.

With the increased popularity of home and office leagues, competition sprouting from every direction and the DFS craze taking over, over the last few years, the granddaddy has quietly fallen out of the limelight. A couple of weeks ago, the company had another ownership change as they were purchased by SportsHub Technologies. CDM founder and FSTA Hall of Famer, Charlie Wiegert, is still a part of the management team and day-to-day decisions. Moreover, two members of the customer service team, Mary and Tracy, are still there to pick up the phone to help with roster switches. Just as they did in the pre-internet days 20 years ago when all roster moves had to be submitted by phone or snail mail.

In an ever-changing industry, it's important for folks to know some of the history and, at the very least, be familiar with a fantasy game that has brought much camaraderie, competition and has sparked some amazing friendships over the years.

Next week I'll delve into the game setup, roster construction, strategies, and some players worth considering at each position. If you want to check the Diamond Challenge out for yourself, you can do so here.