Recently, I was invited to and joined a 30 team Roto/H2H Dynasty Fantasy Baseball League. I’ve been playing fantasy baseball since the late 90’s on the old Sandbox website. Through the years, I’ve played many different types of formats for fantasy baseball and I continuously find myself trending towards competing in Rotisserie Contract leagues. I figured that some of our readers could follow along and maybe together we can ride the waves through the rebuild and trudge up the mountain towards the pinnacle. I don’t envision this being a quick rebuild, given that I’ve got to find a way to beat out 29 other owners, most of whom are doing what they can to also win championships.
In this first article of an ongoing series, I’ll provide some league information and parameters, as well as a snapshot of the roster that I inherited, reviewed, and quickly determined that a rebuild was going to be completely necessary. Keep in mind, contract leagues are different than your standard dynasty league, wherein you’d be able to keep that player for the duration of their career if you wanted to. In a contract league, each year there are roster decisions that have to be made, and those decisions are largely dependent upon the player’s fantasy salary. We’ll get more into the salary specifics as I detail some of the moves already completed.
# of Teams: 30
My team: Oakland Athletics (Each team in the league shares the name of a current MLB franchise). I haven’t decided if I’ll be switching to the Las Vegas A’s or keeping the Oakland roots.
Yearly Entry Fee: $100
League Setup: Each team is placed into their respective American or National League, just like MLB and we play Rotisserie style until the playoffs, then it segues to a Head to Head format. There are payouts for 1st through 6th place in both the AL and NL leagues, as well as for winning each round of the playoffs.
H2H Setup: Top 2 teams receive a bye. Teams 3-6 face off and advance through 4 rounds of playoffs, ultimately crowning a winner.
Roster: 26-man majors (C, 1B, 2B, 3B, SS, LF, CF, RF, UTL, 4SP, 6 RP, 7 BN), 100-man minors (This means upwards of 3000 prospects are rostered!)
Salary Cap: $165,000,000. 2024 Roster salary number was $164,190,000
Finishing spot in 2024 prior to takeover: 25th out of 30 teams.
Taking over a team that finished 25th out of 30 teams felt like I was looking at years and years of mediocrity ahead. I play each league to be competitive for a long stretch, hopefully giving my team a chance to win multiple titles along the way. Here is the inherited roster:
1B: Mitch Moreland
2B: Javier Báez
SS: Marco Luciano
3B: Matt Chapman
CF: Cody Bellinger
RF: Bryce Harper
UTL: Jorge Mateo
BN: Garrett Hampson, Nick Allen, Akil Baddoo
SP: Sandy Alcántara, Chris Sale, Zac Gallen, Trevor Rogers
RP: Dakota Hudson, Ian Hamilton, Hunter Stratton, Ryder Ryan
Notable minor leaguers: Bubba Chandler, Kyle Teel, James Triantos, Jonny Farmelo, Miguel Bleis
On the surface, there are definitely some good players on this team that I could work with, although Harper, Sale and Moreland were all notable free agents after the ’24 season, so I really wasn’t counting on being able to rely upon their services. The more I studied the rosters throughout the league, including my own, the more it became increasingly clear that I would need to rebuild, especially since the current lineup wasn’t able to lift my team out of the bottom third of the league. Gallen looked to be the brightest star on the team and I was going to do what I could to build around him or use his All-Star level production to inject some additional youth and upside into the team.
To date, I’ve made 21 trades, drafted 34 players in our 2025 FYPD, released some players and made a few waiver pickups along the way.
Stay tuned for some upcoming articles that will detail out the trades I’ve made. I’ll also dive into our FYPD and highlight some picks I made that I hope will have a profound impact on taking this low performing team into a perennial title contender!
Born in Arizona. Raised in the Midwest, and with lots of baseball. When I’m not writing about baseball or purchasing my next baseball card, I can be seen coasting down the highway to yet another travel baseball tournament with my wife and son. I love the Braves, bat flips and outfield assists.
Definitely going to enjoy following this story. I’m currently entering year 3 as an expansion team starting from scratch in a 14 team league so I can relate to this. Prospect research is the most important way to turn things around.
Thanks for following, Logan! I’m sure you’re a fully capable owner that knows what you’re doing. If you have a question about a player, trade possibility, draft strategy, etc., feel free to hit me up on Twitter/X at @MKelley_ND!