Pine Lawn Trainwreck Continues, Mayor Pleads Guilty on Extortion Charges and Resigns


Sylvester Caldwell used this obviously Photoshopped portrait of himself sitting in the Oval Office as his official picture on the Pine Lawn city website.
  • Sylvester Caldwell used this obviously Photoshopped portrait of himself sitting in the Oval Office as his official picture on the Pine Lawn city website.

Oh, Sylvester.

The saga of Pine Lawn and its mayor, Sylvester Caldwell, reads like cautionary tale of corruption and petty tyranny in St. Louis' north county. Though the municipality is tiny -- just six-tenths of a square mile -- Pine Lawn's track record of official misconduct has given it a toxic reputation among many residents and neighboring towns. It's a reputation Caldwell has nurtured during his nearly ten-year run as mayor.

On Monday, Caldwell interrupted his own trial in federal court to plead guilty on separate counts of extortion and attempted extortion. According to the St. Louis Post Dispatch, Caldwell's guilty plea came days after a jury saw a recording of him shaking down Eduard Shapshovich, owner of Eddie's Towing in Wellston, by demanding a series of payouts via coded messages about "green Mountain Dew in a cup."

Caldwell agreed to resign as mayor as condition for remaining free on bail until his July 7 sentencing.

During his testimony, Shapshovich said Caldwell had first demanded about $300 every few months, but increased the frequency to every month, and then seemingly at any whim.

See also: Mayor of Pine Lawn Sylvester Caldwell Arrested by FBI, Charged with Extortion

But merely squeezing payments from Shapshovich wasn't the end of Caldwell's extortion and bribery operation. The manager at Pine Lawn Food Market, Akram Samad, also testified that he'd made fourteen payments to Caldwell, each time usually $200 or $300.

"I was scared," Samad said, reports the Post-Dispatch. "He would say, 'I'm in charge of Pine Lawn and the police and the whole city.'"

According to the indictment, "[Caldwell] attempted to disguise the payments as as donations to the City of Pine Lawn, well knowing that the payments were not donations."

But this is where things start to get truly messy. During the court proceedings, Samad also testified that he once helped frame Nakisha Ford, Caldwell's opponent in the 2013 mayoral election, by accusing her of ripping down a pro-Caldwell campaign sign from the store window.

Samad said he'd been contacted by Steven Blakeney, then a Pine Lawn police lieutenant, and was instructed to call 911 to report Ford's "theft." Blakeney then drove to the store to take Samad's report. Ford was later arrested on suspicion of misdemeanor theft and paid a $500 fine. Caldwell won re-election to his third term.

Blakeney is the wild card in this rolling scandal: Once Pine Lawn's top ranking officer, he was fired in December amid allegations that two women he'd met at a bar had woken up in Blakeney's apartment with no memory of how they'd gotten there. The women also described how Blakeney ordered an on-duty Pine Lawn officer to drive them home.

After the firing, Blakeney said the women were lying and accused the city of retaliating against him for cooperating with the FBI investigation against Caldwell.

It remains to be seen if Blakeney can back up his own allegations against the city and Caldwell, but it's worth remembering that Pine Lawn was hardly a picture of civic virtue when Caldwell was elected in 2005.

A 2006 Riverfront Times investigation described numerous financial irregularities in the city's previous administration, and the shenanigans extended from the board of alderman to the city's handling of its employee's insurance benefits.

At the time, Caldwell promised he would be a force for reform in the embattled city.

"The whole administration...from the courts department, housing, public works -- everybody was getting rich off the city," he said. "Even people I brought in, if they're not up to my standards, I'm letting them go. I can admit if I picked a bad apple."

Follow Danny Wicentowski on Twitter at @D_Towski. E-mail the author at


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