Sean "Diddy" Combs appears to be preparing to cool his heels in a jail cell after being sentenced recently to 50 months on prostitution charges. However, People.com reported Diddy's lawyers are vowing to appeal the sentence.

The former rapper, record producer, and record executive, born Sean John Combs in Harlem on November 4, 1969, was formerly known as Puff Daddy and P. Diddy.

The skeptic in me assumed the "Puff" came from a love of ganja, but USA Today reported Sean would "huff and puff" as a child when he didn't get his way.

For the record, the former Catholic altar boy was also a notorious partier.

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Diddy's Connection to Massachusetts

Like many people and things, Sean Combs has a connection to Massachusetts.

In November 2022, Combs announced he would acquire licensed marijuana operations here in Massachusetts and two other states (New York and Illinois), forming a Black-owned cannabis company. The deal was reportedly worth $185 million.

Diddy Tried To Acquire Massachusetts Marijuana Operations
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The Worcester Business Journal reported on November 4, 2022, "Among the dispensaries Combs is buying is the Leicester business formerly known as Cultivate, which was the first legal recreational marijuana dispensary to open east of the Mississippi River when it opened, along with NETA in Northampton, on November 20, 2018."

The other businesses Diddy sought to acquire as part of the deal were Sunnyside locations in Leicester and Worcester and Patriot Care in Greenfield.

Massachusetts Deals Fall Through Amid Diddy's Legal Woes

Alas, Diddy's dream went up in a puff of smoke in 2023 when allegations of sexual misconduct emerged against him.

Diddy's Business on the Vineyard

Combs also had a connection to Martha's Vineyard, where he partnered with the Martha's Vineyard African American Film Festival to highlight Black-owned businesses on the island in August 2022.

90s Classic Hip Hop Joints

Gallery Credit: Dyelon W, Mary K.

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