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If Gray took up ranks with the opposition after signing on with pro-tax campaign committees, it wouldn't have been the first time he crossed the street in the middle of a political campaign.
Gray was hired by former development lawyer Dick King in the 1991 Kansas City mayoral race. The two didn't work well together, and Gray was fired from the campaign. He quickly started working for Brice Harris, a community-college administrator handpicked by the local business community to challenge King.
Both candidates ran an exceptionally sleazy campaign in the primary, a race neither won. Emanuel Cleaver went on to beat Bob Lewellen in that year's general election, marking the first term in the Kansas City mayor's office for the present-day congressman.
And Gray is widely believed to have double-crossed former Jackson County legislator Henry Rizzo in 2010. Gray worked as Rizzo's consultant in a race against 2nd District challenger Crystal Williams. But he also worked on behalf of Terry Riley, another Jackson County Legislature aspirant who was challenging incumbent Fred Arbanas. A mail piece went out that summoned imagery from the crime movie The Usual Suspects by depicting all the incumbents in a police lineup.
"I was shocked to find out that my consultant, who I paid to represent me, was also partly behind the negative mailer that hurt me in the last two weeks of the campaign," Rizzo told The Pitch in 2011.
Rizzo lost that race to Williams. Gray passed Rizzo's complaints off as "political gossip."
Larry Jacob, a political consultant with the Dover Strategy Group, which worked on the pro-tax campaign, says he has been told that Gray defected to opposition groups.
"If, in fact, that did happen — if, in fact, it turns out to be true and he left — he burned a bunch of bridges for no reason," Jacob tells The Pitch.
The sales tax was doomed regardless of Gray's position. But the whose-side-is-he-on-today mystery was just one of many signs indicating a troubled campaign.
Roe says his pre-campaign polling showed that 58 percent of the Jackson County electorate would have voted in favor of the sales tax.
Campaign critics have quietly surmised that such a result came from a push poll — the kind that asks questions in a manner designed to elicit the response a campaign committee wants to hear.
Roe disputes this, saying no reputable firm does push polls.
But there's no doubt that the campaign got off to a terrible start once news of the ballot measure made the front page of the August 8 Kansas City Star. And things didn't get easier once Bradshaw got involved.
Bradshaw, a physician who later became a personal-injury lawyer, has been working on proposing some form of statewide sales tax in Missouri for medical research for the past 30 years. The Jackson County proposal seemed to co-opt some of his ideas, and he set out to defeat it with his own money.
His advertisements against the tax struck early and often between the time the tax was announced and August 27, the date that the Jackson County Legislature approved the measure for the November 5 ballot.
Meanwhile, the pro-tax campaign was unwilling to launch a meaningful election effort before legislators could look over the issue. This allowed Bradshaw's criticisms of the tax to go without a rebuttal.
"Bradshaw tried to kill us in the crib before the Legislature had even voted to put it on the ballot," Roe tells The Pitch. He says the early polling lead was whittled down 10 points because of Bradshaw's work.