Structured Settlements 4Real®Blog 2026

Structured settlements expert John Darer reviews the latest structured settlements and settlement planning information and news, and provides expert opinion and highly regarded commentary. that is spicy, Informative, irreverent and effective for over 20 years.

by Structured Settlement Watchdog

Under the guise of “structured settlement news”, an October 19, 2020 post by Milestone CEO and CrowFly DirectorJohn Bair, using the Legal Examiner spinoff Scare Crow 2020from Injury Board as a non-lawyer, promotes further sales of structured settlement payments using the image of an African American family. Today, with this example, together with my June 2018 observation about enuities.com (a precursor to CrowFly), it’s remarkable that people of color are Bair/CrowFly’s target image, when the well documented and ongoing predatory behavior of the structured settlement secondary market is color blind.

  • Bair, through his associated companies,  uniquely retains all of his structured settlement general agency appointments* with Milestone Consulting, despite repeatedly trashing structured settlements through various social media, including the Injury Board spinoff, and through his structured settlement factoring origination firm CrowFly*, heavily promoting structured settlement factoring, now for repeat sales. 
  • On April 20, 2020, Bair sent an email blast from Milestone to “eliminate annuities from client portfolios and settlement plans”

In previous posts we’ve drawn attention to the inherent conflict of interest that exists between a series of entities (literally under one roof), that solicit pre-settlement cash advances, structured settlement annuities, the factoring and refactoring of structured settlement payment streams.

According to an analytics program, CrowFly’s estimated daily paid ad word spend has been over $2,000. Top key words bought for the period ending July 1, 2020 were versions of JG Wentworth. Both Milestone and CrowFly share the same office space in Buffalo New York at 737 Main Street.  In spite of being at times promoted as a FinTech firm, in October 2018 using his Milestone Consulting email, Bair bragged that his was the only structured settlement primary as well as structured settlement factoring origination firm that he knew of.

* Upon information and belief Milestone is not contracted with USAA Life, American General or United States Life.

 

 

 

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