diff --git a/.gitignore b/.gitignore
index b8a2181..9500d65 100644
--- a/.gitignore
+++ b/.gitignore
@@ -219,3 +219,4 @@ __marimo__/
 # Project-specific
 data/
 production_logs/
+*.json
diff --git a/services/draft_pick_service.py b/services/draft_pick_service.py
new file mode 100644
index 0000000..939f8fb
--- /dev/null
+++ b/services/draft_pick_service.py
@@ -0,0 +1,312 @@
+"""
+Draft pick service for Discord Bot v2.0
+
+Handles draft pick CRUD operations. NO CACHING - draft data changes constantly.
+"""
+import logging
+from typing import Optional, List
+
+from services.base_service import BaseService
+from models.draft_pick import DraftPick
+from exceptions import APIException
+
+logger = logging.getLogger(f'{__name__}.DraftPickService')
+
+
+class DraftPickService(BaseService[DraftPick]):
+    """
+    Service for draft pick operations.
+
+    IMPORTANT: This service does NOT use caching decorators because draft picks
+    change constantly during an active draft. Always fetch fresh data.
+
+    Features:
+    - Get pick by overall number
+    - Get picks by team
+    - Get picks by round
+    - Update pick with player selection
+    - Query available/taken picks
+    """
+
+    def __init__(self):
+        """Initialize draft pick service."""
+        super().__init__(DraftPick, 'draftpicks')
+        logger.debug("DraftPickService initialized")
+
+    async def get_pick(self, season: int, overall: int) -> Optional[DraftPick]:
+        """
+        Get specific pick by season and overall number.
+
+        NOT cached - picks change during draft.
+
+        Args:
+            season: Draft season
+            overall: Overall pick number
+
+        Returns:
+            DraftPick instance or None if not found
+        """
+        try:
+            params = [
+                ('season', str(season)),
+                ('overall', str(overall))
+            ]
+
+            picks = await self.get_all_items(params=params)
+
+            if picks:
+                pick = picks[0]
+                logger.debug(f"Found pick #{overall} for season {season}")
+                return pick
+
+            logger.debug(f"No pick found for season {season}, overall #{overall}")
+            return None
+
+        except Exception as e:
+            logger.error(f"Error getting pick season={season} overall={overall}: {e}")
+            return None
+
+    async def get_picks_by_team(
+        self,
+        season: int,
+        team_id: int,
+        round_start: int = 1,
+        round_end: int = 32
+    ) -> List[DraftPick]:
+        """
+        Get all picks owned by a team in a season.
+
+        NOT cached - picks change as they're traded.
+
+        Args:
+            season: Draft season
+            team_id: Team ID that owns the picks
+            round_start: Starting round (inclusive)
+            round_end: Ending round (inclusive)
+
+        Returns:
+            List of DraftPick instances owned by team
+        """
+        try:
+            params = [
+                ('season', str(season)),
+                ('owner_team_id', str(team_id)),
+                ('round_start', str(round_start)),
+                ('round_end', str(round_end)),
+                ('sort', 'order-asc')
+            ]
+
+            picks = await self.get_all_items(params=params)
+            logger.debug(f"Found {len(picks)} picks for team {team_id} in rounds {round_start}-{round_end}")
+            return picks
+
+        except Exception as e:
+            logger.error(f"Error getting picks for team {team_id}: {e}")
+            return []
+
+    async def get_picks_by_round(
+        self,
+        season: int,
+        round_num: int,
+        include_taken: bool = True
+    ) -> List[DraftPick]:
+        """
+        Get all picks in a specific round.
+
+        NOT cached - picks change as they're selected.
+
+        Args:
+            season: Draft season
+            round_num: Round number
+            include_taken: Whether to include picks with players selected
+
+        Returns:
+            List of DraftPick instances in the round
+        """
+        try:
+            params = [
+                ('season', str(season)),
+                ('pick_round_start', str(round_num)),
+                ('pick_round_end', str(round_num)),
+                ('sort', 'order-asc')
+            ]
+
+            if not include_taken:
+                params.append(('player_taken', 'false'))
+
+            picks = await self.get_all_items(params=params)
+            logger.debug(f"Found {len(picks)} picks in round {round_num}")
+            return picks
+
+        except Exception as e:
+            logger.error(f"Error getting picks for round {round_num}: {e}")
+            return []
+
+    async def get_available_picks(
+        self,
+        season: int,
+        overall_start: Optional[int] = None,
+        overall_end: Optional[int] = None
+    ) -> List[DraftPick]:
+        """
+        Get picks that haven't been selected yet.
+
+        NOT cached - availability changes constantly.
+
+        Args:
+            season: Draft season
+            overall_start: Starting overall pick number (optional)
+            overall_end: Ending overall pick number (optional)
+
+        Returns:
+            List of available DraftPick instances
+        """
+        try:
+            params = [
+                ('season', str(season)),
+                ('player_taken', 'false'),
+                ('sort', 'order-asc')
+            ]
+
+            if overall_start is not None:
+                params.append(('overall_start', str(overall_start)))
+            if overall_end is not None:
+                params.append(('overall_end', str(overall_end)))
+
+            picks = await self.get_all_items(params=params)
+            logger.debug(f"Found {len(picks)} available picks")
+            return picks
+
+        except Exception as e:
+            logger.error(f"Error getting available picks: {e}")
+            return []
+
+    async def get_recent_picks(
+        self,
+        season: int,
+        overall_end: int,
+        limit: int = 5
+    ) -> List[DraftPick]:
+        """
+        Get recent picks before a specific pick number.
+
+        NOT cached - recent picks change as draft progresses.
+
+        Args:
+            season: Draft season
+            overall_end: Get picks before this overall number
+            limit: Number of picks to retrieve
+
+        Returns:
+            List of recent DraftPick instances (reverse chronological)
+        """
+        try:
+            params = [
+                ('season', str(season)),
+                ('overall_end', str(overall_end - 1)),  # Exclude current pick
+                ('player_taken', 'true'),  # Only taken picks
+                ('sort', 'order-desc'),  # Most recent first
+                ('limit', str(limit))
+            ]
+
+            picks = await self.get_all_items(params=params)
+            logger.debug(f"Found {len(picks)} recent picks before #{overall_end}")
+            return picks
+
+        except Exception as e:
+            logger.error(f"Error getting recent picks: {e}")
+            return []
+
+    async def get_upcoming_picks(
+        self,
+        season: int,
+        overall_start: int,
+        limit: int = 5
+    ) -> List[DraftPick]:
+        """
+        Get upcoming picks after a specific pick number.
+
+        NOT cached - upcoming picks change as draft progresses.
+
+        Args:
+            season: Draft season
+            overall_start: Get picks after this overall number
+            limit: Number of picks to retrieve
+
+        Returns:
+            List of upcoming DraftPick instances
+        """
+        try:
+            params = [
+                ('season', str(season)),
+                ('overall_start', str(overall_start + 1)),  # Exclude current pick
+                ('sort', 'order-asc'),  # Chronological order
+                ('limit', str(limit))
+            ]
+
+            picks = await self.get_all_items(params=params)
+            logger.debug(f"Found {len(picks)} upcoming picks after #{overall_start}")
+            return picks
+
+        except Exception as e:
+            logger.error(f"Error getting upcoming picks: {e}")
+            return []
+
+    async def update_pick_selection(
+        self,
+        pick_id: int,
+        player_id: int
+    ) -> Optional[DraftPick]:
+        """
+        Update a pick with player selection.
+
+        Args:
+            pick_id: Draft pick database ID
+            player_id: Player ID being selected
+
+        Returns:
+            Updated DraftPick instance or None if update failed
+        """
+        try:
+            update_data = {'player_id': player_id}
+            updated_pick = await self.patch(pick_id, update_data)
+
+            if updated_pick:
+                logger.info(f"Updated pick #{pick_id} with player {player_id}")
+            else:
+                logger.error(f"Failed to update pick #{pick_id}")
+
+            return updated_pick
+
+        except Exception as e:
+            logger.error(f"Error updating pick {pick_id}: {e}")
+            return None
+
+    async def clear_pick_selection(self, pick_id: int) -> Optional[DraftPick]:
+        """
+        Clear player selection from a pick (for admin wipe operations).
+
+        Args:
+            pick_id: Draft pick database ID
+
+        Returns:
+            Updated DraftPick instance with player cleared, or None if failed
+        """
+        try:
+            update_data = {'player_id': None}
+            updated_pick = await self.patch(pick_id, update_data)
+
+            if updated_pick:
+                logger.info(f"Cleared player selection from pick #{pick_id}")
+            else:
+                logger.error(f"Failed to clear pick #{pick_id}")
+
+            return updated_pick
+
+        except Exception as e:
+            logger.error(f"Error clearing pick {pick_id}: {e}")
+            return None
+
+
+# Global service instance
+draft_pick_service = DraftPickService()
diff --git a/utils/draft_helpers.py b/utils/draft_helpers.py
new file mode 100644
index 0000000..e251cfd
--- /dev/null
+++ b/utils/draft_helpers.py
@@ -0,0 +1,232 @@
+"""
+Draft utility functions for Discord Bot v2.0
+
+Provides helper functions for draft order calculation and cap space validation.
+"""
+import math
+from typing import Tuple
+from utils.logging import get_contextual_logger
+
+logger = get_contextual_logger(__name__)
+
+
+def calculate_pick_details(overall: int) -> Tuple[int, int]:
+    """
+    Calculate round number and pick position from overall pick number.
+
+    Hybrid draft format:
+    - Rounds 1-10: Linear (same order every round)
+    - Rounds 11+: Snake (reverse order on even rounds)
+
+    Special rule: Round 11, Pick 1 belongs to the team that had Round 10, Pick 16
+    (last pick of linear rounds transitions to first pick of snake rounds).
+
+    Args:
+        overall: Overall pick number (1-512 for 32-round, 16-team draft)
+
+    Returns:
+        (round_num, position): Round number (1-32) and position within round (1-16)
+
+    Examples:
+        >>> calculate_pick_details(1)
+        (1, 1)  # Round 1, Pick 1
+
+        >>> calculate_pick_details(16)
+        (1, 16)  # Round 1, Pick 16
+
+        >>> calculate_pick_details(160)
+        (10, 16)  # Round 10, Pick 16 (last linear pick)
+
+        >>> calculate_pick_details(161)
+        (11, 1)  # Round 11, Pick 1 (first snake pick - same team as 160)
+
+        >>> calculate_pick_details(176)
+        (11, 16)  # Round 11, Pick 16
+
+        >>> calculate_pick_details(177)
+        (12, 16)  # Round 12, Pick 16 (snake reverses)
+    """
+    round_num = math.ceil(overall / 16)
+
+    if round_num <= 10:
+        # Linear draft: position is same calculation every round
+        position = ((overall - 1) % 16) + 1
+    else:
+        # Snake draft: reverse on even rounds
+        if round_num % 2 == 1:  # Odd rounds (11, 13, 15...)
+            position = ((overall - 1) % 16) + 1
+        else:  # Even rounds (12, 14, 16...)
+            position = 16 - ((overall - 1) % 16)
+
+    return round_num, position
+
+
+def calculate_overall_from_round_position(round_num: int, position: int) -> int:
+    """
+    Calculate overall pick number from round and position.
+
+    Inverse operation of calculate_pick_details().
+
+    Args:
+        round_num: Round number (1-32)
+        position: Position within round (1-16)
+
+    Returns:
+        Overall pick number
+
+    Examples:
+        >>> calculate_overall_from_round_position(1, 1)
+        1
+
+        >>> calculate_overall_from_round_position(10, 16)
+        160
+
+        >>> calculate_overall_from_round_position(11, 1)
+        161
+
+        >>> calculate_overall_from_round_position(12, 16)
+        177
+    """
+    if round_num <= 10:
+        # Linear draft
+        return (round_num - 1) * 16 + position
+    else:
+        # Snake draft
+        picks_before_round = (round_num - 1) * 16
+        if round_num % 2 == 1:  # Odd snake rounds
+            return picks_before_round + position
+        else:  # Even snake rounds (reversed)
+            return picks_before_round + (17 - position)
+
+
+async def validate_cap_space(
+    roster: dict,
+    new_player_wara: float
+) -> Tuple[bool, float]:
+    """
+    Validate team has cap space to draft player.
+
+    Cap calculation:
+    - Maximum 32 players on active roster
+    - Only top 26 players count toward cap
+    - Cap limit: 32.00 sWAR total
+
+    Args:
+        roster: Roster dictionary from API with structure:
+            {
+                'active': {
+                    'players': [{'id': int, 'name': str, 'wara': float}, ...],
+                    'WARa': float  # Current roster sWAR
+                }
+            }
+        new_player_wara: sWAR value of player being drafted
+
+    Returns:
+        (valid, projected_total): True if under cap, projected total sWAR after addition
+
+    Raises:
+        ValueError: If roster structure is invalid
+    """
+    if not roster or not roster.get('active'):
+        raise ValueError("Invalid roster structure - missing 'active' key")
+
+    active_roster = roster['active']
+    current_players = active_roster.get('players', [])
+
+    # Calculate how many players count toward cap after adding new player
+    current_roster_size = len(current_players)
+    projected_roster_size = current_roster_size + 1
+
+    # Maximum zeroes = 32 - roster size
+    # Maximum counted = 26 - zeroes
+    max_zeroes = 32 - projected_roster_size
+    max_counted = min(26, 26 - max_zeroes)  # Can't count more than 26
+
+    # Sort all players (including new) by sWAR descending
+    all_players_wara = [p['wara'] for p in current_players] + [new_player_wara]
+    sorted_wara = sorted(all_players_wara, reverse=True)
+
+    # Sum top N players
+    projected_total = sum(sorted_wara[:max_counted])
+
+    # Allow tiny floating point tolerance
+    is_valid = projected_total <= 32.00001
+
+    logger.debug(
+        f"Cap validation: roster_size={current_roster_size}, "
+        f"projected_size={projected_roster_size}, "
+        f"max_counted={max_counted}, "
+        f"new_player_wara={new_player_wara:.2f}, "
+        f"projected_total={projected_total:.2f}, "
+        f"valid={is_valid}"
+    )
+
+    return is_valid, projected_total
+
+
+def format_pick_display(overall: int) -> str:
+    """
+    Format pick number for display.
+
+    Args:
+        overall: Overall pick number
+
+    Returns:
+        Formatted string like "Round 1, Pick 3 (Overall #3)"
+
+    Examples:
+        >>> format_pick_display(1)
+        "Round 1, Pick 1 (Overall #1)"
+
+        >>> format_pick_display(45)
+        "Round 3, Pick 13 (Overall #45)"
+    """
+    round_num, position = calculate_pick_details(overall)
+    return f"Round {round_num}, Pick {position} (Overall #{overall})"
+
+
+def get_next_pick_overall(current_overall: int) -> int:
+    """
+    Get the next overall pick number.
+
+    Simply increments by 1, but provided for completeness and future logic changes.
+
+    Args:
+        current_overall: Current overall pick number
+
+    Returns:
+        Next overall pick number
+    """
+    return current_overall + 1
+
+
+def is_draft_complete(current_overall: int, total_picks: int = 512) -> bool:
+    """
+    Check if draft is complete.
+
+    Args:
+        current_overall: Current overall pick number
+        total_picks: Total number of picks in draft (default: 512 for 32 rounds, 16 teams)
+
+    Returns:
+        True if draft is complete
+    """
+    return current_overall > total_picks
+
+
+def get_round_name(round_num: int) -> str:
+    """
+    Get display name for round.
+
+    Args:
+        round_num: Round number
+
+    Returns:
+        Display name like "Round 1" or "Round 11 (Snake Draft Begins)"
+    """
+    if round_num == 1:
+        return "Round 1"
+    elif round_num == 11:
+        return "Round 11 (Snake Draft Begins)"
+    else:
+        return f"Round {round_num}"