Irony of no sympathy
The Naval institute that Ronnie had enrolled in, was merciless to Ronnie. They instantly expelled him out of the school even if he was just a young boy with no record of stealing. Although the true culprit who stole Elliot's money was not revealed, Ronnie said he and Elliot were best friends yet Elliot didn't defend Ronnie.
Irony of wealth
The play begins with the wealthy Winslow family and ends with them losing their money. It is a dramatic irony that shows the development of the characters and their situation.
Irony of loss
Each of the family members in 'the Winslow boy' had experienced a certain loss throughout the story. It all begins with Ronnie being accused of theft, and then Arthur getting sick and losing money, to Dickie having to drop school as Arthur couldn't afford his fees, Catherine's marriage failure and having to reject Desmond's proposal, and Grace needing to tell Violet she was going to be fired. Violet was so close to the family that she too, faced an issue of loss, although towards the end Grace never told Violet she was fired.
Irony of title
The play's title is 'the Winslow boy' yet the entire story revolves around the domino effect of how one problem can lead to another. The play focuses on the Winslow family facing their issues and solving it together or by themselves.
Not only is the play about the family, but outside characters such as Desmond and Sir Robert are also involved. Where Sir Robert's reputation was being tested as if he didn't win that case, it would've been damaging to his career.
Irony of determination
Determination is usually seen as a good thing, whereas in this play, the audience gets the benefit of the doubt of whether determination had lead to the Winslow family's downfall or their success.
Determination had lead to the Winslow family losing their fortunes spending years on fighting a case instead of having family bonding time. Catherine and Grace have frequently warned Arthur to drop the case yet Arthur and Sir Roberts continue to pursue it, knowing it is risky, but having hope and faith that in the end it'll work out.
