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Judge Dennis H. Strickland is a judge in the Hope County Court.
Judge Strickland worked in Hope, South Dakota as a criminal judge. Despite having a reputation for being tough but fair (according to a dialogue in Skurky's Law), he is apparently aware of Sheriff Skurky's corruption yet shows no objection to it. After learning that he is of recent British ancestry, he became obsessed with all things British and started dressing in a full-bottomed wig and a British-style judges ceremonial robes at work and even having court transcribers rewrite some profanities into British English counterparts, such as "asshole" into "arsehole".
- During cases, he often draws comparisons to his own personal life, some of them being very thinly related to matters at hand. For example, Strickland admits to having a low view of the UN. He also admits to strongly disliking his brother-in-law because he is a "drunken, gambling ass."
- He states that he most frequently gives the minimum sentences for crimes, suggesting he favors rehabilitation or has a forgiving and lenient attitude. However, he makes an exception for Timothy Hawke, possibly because he is a repeat offender.
- It is likely he is a golfer, as suggested by the multiple golf club's in his office.
- Strickland's voice is noticeably different after the opening cut-scene of Skurky's Law.
- According to a local Hope news radio station, Strickland was under investigation by the FBI in connection to a bribe scandal. The previous year he was under investigation for lack of professional judgement in numerous cases, including worker compensation cases involving Dexter Industries (suggesting that he is on Dexter's payroll as well), as well as repeatedly acquitting James Seth Lynch.
- His name may be a reference to Gerald Strickland, the principal of Hill Valley High School in the film series Back To The Future. Gerald Strickland strongly believed in discipline and order, and had a reputation for being harsh on those he deemed 'slackers'.