Monk series’ handling of Trudy’s death.

The despicable villain Dale the Whale has long since divided fans in each of his three iterations; while some love to hate his character, others hate him outright. Biederbeck’s importance in the eventual solving of Trudy’s murder in the Monk season 8 finale is undeniable regardless of reception, but the execution of this character left something to be desired.

Who Is Dale “The Whale” Biederbeck In Monk

This Wealthy Financier Had A Strange Connection To Trudy

Dale the Whale is a wealthy financier who, in the words of Adrian Monk, “owns half the city with…you know, an option on the other half.” Two years before her death, Trudy had written an article that publicly insulted Biederbeck, leading him to sue both her and the publication. According to Stottlemeyer (Ted Levine), Biederbeck was also known to buy out newspapers for the sole reason of keeping his name out of them. This drawn-out legal battle created a deep-seated animosity between Mr. Monk and Dale the Whale, tragically causing Trudy and Adrian to lose their home.

In season 1, episode 4, “Mr. Monk Meets Dale the Whale,” Dale (Adam Arkin) enlists Adrian to prove his innocence in the murder of Judge Catherine Lavinio, whose ruling against Biederbeck cost him $210 million. Ironically, Adrian instead proves his guilt, landing Dale in prison. Despite their hatred for one another, the revelation that Dale holds key information about Trudy’s death leads Monk to strike a bargain with him, trading Biederbeck's prison privileges for leads in his wife’s murder. Throughout the series, Dale slowly feeds tidbits of information to Adrian and the SFPD regarding who killed Trudy Monk.

Why Dale Was Played By Three Different Actors

Adam Arkin, Tim Curry, and Ray Porter All Played The Same Role

With three appearances in the series, it is undeniably strange for the character of Dale the Whale to be played by a different actor each time. Initially portrayed by Adam Arkin in season 1, the character of Biederbeck was soon replaced in season 2 with one of the best Monk guest stars of all time, Tim Curry. However, this star’s presence on the show was short-lived; presumably, Tim Curry’s schedule could not accommodate a serialized Monk role, and so Dale the Whale was recast a final time with actor Ray Porter in season 6.

Adam Arkin decided not to continue in this villainous Monk role, a choice which may have been due to the potential for typecasting. After all, Dale the Whale’s character is especially memorable and distinctive. It is more likely, however, that Arkin (and possibly even Curry) abandoned the part because of its taxing nature. For such a brief amount of screen time, the Dale the Whale role required actors to spend hours in makeup and wear a special suit, which had to have been very uncomfortable and may not have felt worth it, even to these dedicated actors.

Dale Playing Such A Small Role Was A Missed Opportunity For Monk

The Show Wasted The Potential For A Memorable Serialized Villain

Unfortunately, the recurrent recasting of this memorable Monk mogul might have meant a missed opportunity for the series. With its episodic nature and the comparably small amount of time that the show spent on the Trudy murder arc – ostensibly the main point of the show – Monk would have benefitted from Dale the Whale playing a more serialized role. There is no true villain who provides consistent friction in the Monk series, and Dale the Whale would have fit the bill perfectly as a credible nemesis to Adrian, rather than more comical enemies like Harold Krenshaw (Tim Bagley).

Dale the Whale's first appearance references Silence of the Lambs (1991): much like Dr. Hannibal Lecter, Dale leverages his knowledge in exchange for a window and other privileges while incarcerated. The Monk character may additionally be a reference to a similar villain from the Hannibal franchise, Mason Verger, who also happens to be bedbound following his encounter with Dr. Lecter.

Monk had many twists involving Trudy’s death, and almost every single one linked back to Biederbeck – and yet this potential was ultimately wasted by the Monk writers, with Dale’s involvement being largely forgotten after season 6. Especially given the epic conclusion to Trudy’s case in the Monk season 8 finale, Dale the Whale’s character presented a great opportunity for the writers to bring everything full circle.

Instead, a character who had unbelievable potential as a unique villain was left to fall flat. This was largely due to Dale the Whale’s inconsistent casting as well as the show creators’ failure to preemptively plan out the character’s involvement. Not knowing how Trudy’s murder would be solved when writing began led elements like Dale the Whale to seem relatively pointless. Especially if Tim Curry had been retained past Monk season 2, the web of Trudy’s murder could have been handled in a much more dramatic and effective way, and possibly even incorporated into a Mr. Monk’s Last Case sequel.