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Woolsey is a defensive agreement to compete over your opponent's 1NT opening bid.  The convention is named after its creator Kit Woolsey, a bridge professional and author.  The Woolsey offers several ways to show a 2-suited overcall.  The benefits of Woolsey include:

  1. Helping the partnership choose the overcaller's better major when the advancer (the overcaller's partner) does not have a preference
  2. Distinguishing overcalls with a minor and a 4-card major from overcalls with a minor and a 5+ card major, helping the partnership choose the right strain

The Woolsey convention works as follows over a 1NT opening bid:

  • 2♣ is artificial, showing both majors. at least 4-4.  If the advancer doesn't have a preference between the majors, advancer can bid an artificial 2 to ask opener to bid their better major.
  • 2 is artificial, showing an undisclosed 6+ card major.  
  • 2 shows 5+ hearts and 4+ cards in an undisclosed minor. 
  • 2♠ shows 5+ spades and 4+ cards in an undisclosed minor
  • 2NT is an artificial bid showing both minors  
  • Double is artificial, showing an undisclosed 4-card major and an undisclosed 5+ card minor

Let's look at advancer's options after a Woolsey double or overcall.  

After 1NT - X1 - Pass,    1artificial, showing an undisclosed 4-card major and an undisclosed 5+ card minor
Advancer bids:

  • 2♣ says they want to play in their partner's long minor.  The doubler passes with long clubs.  The doubler bids 2 with long diamonds.  Over 2, advancer can bid 2 to ask to play in the doubler's major
  • 2 asks the doubler to bid their 4-card major, after overcaller's 2M bid, advancer bids:
    • 2NT to ask for overcaller's minor
    • 3♣ to play, was interested in other major
    • 3♦ to play, was interested in other major
    • 3M is invitational
  • 2 shows a long heart suit and is an offer to play
  • 2♠ shows a long spade suit and is an offer to play

After 1NT - 2♣2 - Pass,     2artificial, showing both majors. at least 4-4
Advancer bids:

  • 2 asks the overcaller to bid their better major
  • 2 shows a preference for hearts
  • 2♠ shows a preference for spades

After 1NT - 23 - Pass,      3artificial, showing an unspecified 6+ card major
We recommend using a "paradox" style when advancing the 2 overcall.  If the overcaller's partner is interested in a heart game, but not a spade game, they cannot afford to make a pass or correct 2♥ bid.  Instead, they bid 2♠ which asks their partner to pass if their suit is spades.  If their suit is hearts, they bid 3if unwilling to accept a game try in hearts.  If the overcaller has hearts and is willing to accept a game try, they make a descriptive call other than 3.

  • 2 says they are willing to stop in 2 if overcaller's suit is heart.  Otherwise, overcaller corrects to 2♠
  • 2♠ says they want to stop in 2♠ if opener's suit is spades.  It shows a fit and possibly game interest if overcaller's suit is hearts

After 1NT - 24 - Pass,      4artificial, showing 5+ hearts and 4+ cards in an unspecified minor
Advancer bids:

  • Pass to play 2
  • 2♠ is a natural offer to play showing a long spade suit
  • 3♣ asks to play in overcaller's minor.  Overcaller pass with clubs and bids 3 with diamonds

Generally, a 2NT bid by advancer is an artificial game try asking their partner to describe their hand.  If the opponents bid or double, a double or redouble typically asks partner to describe their hand.  

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