Opening Day is March 26, 2026. If you're a fantasy baseball commissioner — especially in a keeper or dynasty league — the next six weeks are the most important stretch of your offseason. This is when keeper deadlines get set, rules get clarified, drafts get scheduled, and the foundation for a smooth season gets laid.
Or, if you're like most commissioners, this is when you scramble to do everything at the last minute and hope nobody notices the cracks.
This checklist is designed to be actionable and sequential. Work through it from top to bottom between now and draft day, and you'll have a well-organized league that runs itself — or at least close to it.
February: The Foundation
February is for planning. Don't draft yet. Don't even think about draft order yet. Handle the structural work first.
Confirm Your Roster
Before you do anything else, confirm that all your managers are returning. Send a message to the group chat — not a casual mention, a direct "reply yes if you're in for 2026" message. Set a deadline (February 15 is reasonable) and follow up individually with anyone who doesn't respond.
If you need replacement managers, start looking now. Finding a good fantasy baseball manager takes time, especially for keeper leagues where they're inheriting someone else's roster. The earlier you know your roster of owners, the better.
Review and Update League Rules
Pull up your league constitution (you have one, right?) and review it. Look for:
- Ambiguities from last season: Were there any arguments about rules? Any situations where you had to make a judgment call? Document the precedent or update the rule to prevent it from happening again.
- Keeper rule clarity: Are keeper costs, year limits, and eligibility rules explicitly documented? If anything is "understood" but not written down, write it down now.
- Scoring changes: Does your league want to adjust scoring categories? Add OBP instead of AVG? Switch to points from categories? These conversations need to happen in February, not March.
- Roster size adjustments: Adding a utility spot? Expanding the bench? Changing IL slots? These affect keeper decisions, so they must be finalized before keeper deadlines.
Tip: If you're making any rule changes, put them to a league vote with a clear deadline. Majority or two-thirds approval (whatever your constitution specifies) with at least a week for discussion. Don't spring rule changes on people.
Set Your Keeper Deadline
This is arguably the most important date on your calendar. Set it early enough that managers have time to think and negotiate trades, but late enough that spring training news can inform decisions. For a March 26 Opening Day, a keeper deadline of March 7-14 is ideal.
Communicate the deadline clearly and repeatedly. Pin it in the group chat. Send a reminder one week before and three days before. Decide in advance what happens if someone misses the deadline — do their keepers default to last year's? Do they lose keeper slots? Whatever the penalty, it should be established and known.
Commissioner pro tip: Use KeeperTracker to generate a keeper eligibility report for the entire league and share it with all managers before the deadline. When everyone can see their options clearly, the deadline goes smoothly and you don't get panicked last-minute questions.
Collect League Dues
If your league has a buy-in, collect it in February. Not at the draft. Not "whenever." February. Managers who haven't paid by keeper deadline shouldn't be allowed to make keeper selections. This sounds harsh, but it's the single most effective way to ensure everyone is committed and engaged.
Use Venmo, PayPal, LeagueSafe, or whatever your league prefers. Just make sure money is collected before the important decisions start. Chasing payments in April when someone's team is 2-8 is a nightmare.
Early March: Keeper Season
Facilitate Keeper Trades
The period between early February and the keeper deadline is prime trading season. Managers are evaluating their keeper options and looking for deals. As commissioner, your job is to:
- Process trades promptly (within 24 hours)
- Verify that traded keeper costs are correctly transferred
- Ensure any trade deadline you've set is enforced
- Communicate all approved trades to the league
Some leagues allow keeper-for-pick trades right up until the keeper deadline. Others freeze trades a few days before. Whatever your rule, enforce it consistently.
Verify All Keeper Selections
When the keeper deadline arrives, verify every team's selections. Check for:
- Players who have exceeded their maximum keeper years
- Keeper costs that don't match your records
- Teams keeping more players than allowed
- Players who were traded and may have changed keeper eligibility
- Waiver pickups with incorrect keeper cost assignments
This is tedious work if you're doing it manually. It's exactly the kind of validation that a tool like KeeperTracker handles automatically — flagging ineligible selections and cost discrepancies before they become arguments on draft night.
Announce Keepers League-Wide
Once keepers are verified, publish the full list to the league. Every team's keepers, their costs, and the corresponding draft picks that are forfeited. Transparency here is critical — it lets managers plan their draft strategy and flags any errors before they're locked in.
Mid-March: Draft Preparation
Set Draft Date and Time
For leagues drafting before Opening Day (March 26), you're looking at a draft window of roughly March 14-25. Use a poll to find the best date. Account for time zones if your league is spread out.
Live draft vs. slow draft: Live drafts are more fun and social. Slow drafts (8-12 hours per pick) are more practical for busy adults. If you're doing a slow draft, start earlier — a 20-round slow draft at 8 hours per pick takes almost a week.
Determine Draft Order
How you set draft order depends on your league's traditions, but common methods include:
- Reverse standings: Worst team from last season picks first. Rewards bad teams but can incentivize tanking.
- Lottery: Randomized order with weighted odds based on standings. Prevents tanking while still helping bad teams.
- Pure random: Everyone has equal odds. Simplest and hardest to argue with.
- Keeper-adjusted: Teams with better keepers draft later. Rarely used but theoretically fair.
Whatever method you use, run it transparently. Do the lottery on video call, use a verifiable randomizer, or let the platform generate the order. Draft order arguments are poison.
Configure Platform Settings
Log into your fantasy platform and verify all settings before the draft:
- Roster positions: C, 1B, 2B, SS, 3B, OF, UTIL, SP, RP, BN, IL — confirm everything matches your rules.
- Scoring settings: Double-check every category or point value. One wrong setting discovered in May is embarrassing; discovered in September during a playoff race is catastrophic.
- Waiver settings: FAAB vs. rolling waivers, waiver period length, trade review period.
- Playoff format: Number of teams, start date, matchup length. Set this now so everyone knows the target from day one.
- Keeper designations: Enter all verified keepers into the platform so the draft board reflects them correctly.
Prepare a Draft Sheet
Share a pre-draft document showing:
- All keepers by team with their round costs
- Draft order
- Available picks per team (accounting for keeper forfeitures)
- Any picks that were traded
This is especially important in keeper leagues where different teams have different picks available. A manager who traded their 3rd-round pick needs to know that before the draft, not during it.
Draft Week: Final Checks
Send a Draft Day Reminder
Two days before the draft, send a reminder with all the logistics: date, time, platform, format (snake/auction), and any special rules (pick time limits, auto-draft settings for absent managers).
Have a Backup Plan
What happens if someone doesn't show up? Set auto-draft preferences as a safety net. What if the platform crashes? (It happens.) Have a contingency — even if it's just "we'll reschedule for tomorrow."
Test the Platform
Do a quick check on your fantasy platform the day before the draft. Make sure all settings are saved, all keepers are entered, and the draft lobby is configured correctly. Finding a settings error during the draft is preventable chaos.
Post-Draft: Set It and (Don't) Forget It
Verify Draft Results
After the draft, spot-check the results. Did keepers get assigned to the correct rounds? Did traded picks go to the right teams? Did the draft order follow your rules? Catch errors now — they're much harder to fix three weeks into the season.
Send a Season Kickoff Message
Post a message to the league with key dates: trade deadline, waiver wire rules, playoff start date, and — critically — the process for keeper tracking going forward. If you're using KeeperTracker, this is a great time to share access so managers can start thinking about next year's keepers from day one.
Document Everything
Save the draft results, keeper lists, and all rule documents somewhere permanent. You'll need them next February when this whole process starts again. Start tracking keeper-relevant transactions (trades, waiver pickups, draft picks) from day one — your future self will thank you.
The Commissioner's Secret Weapon
The difference between a good commissioner and a great one isn't fantasy knowledge — it's organization. The checklist above is a lot of work, but most of it is administrative, not strategic. The commissioners who run leagues that last a decade are the ones who treat the administrative work seriously and have systems to handle it efficiently.
Tools like KeeperTracker exist specifically to take the most painful parts of this checklist — keeper eligibility verification, cost tracking, and league-wide reporting — and automate them. But even without specialized tools, following a structured checklist like this one will put you ahead of 90% of fantasy baseball commissioners.
Opening Day is coming. Your league is counting on you. Get to work.