The character of Jamison, as played by John DiGiacomo, was a little more than a blip in the Federation running from 1989 to 1992. I've also seen the character called Jameson and Jameson Winger, so use your choice on this.
So, what was so terrible about him? He was depicted as your typical dork (not a nerd, as nerds and geeks are usually portrayed as smart, knowledgeable about something. Jamison was just an idiot), i.e. messy hair, clothes not fitting, and having the social skills of a bad tie.
He mostly appeared on and suffered abuse at the hands of Bobby "the Brain" Heenan on his talk show before becoming the manager of the Bushwackers. I'm a bit baffled at the objection to the character, as he really didn't do anything too annoying. He wasn't much a talker, didn't involve himself in the matches too often, and generally did very little to bring attention to himself.
I also heard that Jamison was meant as an attack on Jim Cornette but I've not seen anything concrete regarding that. Plus why would they make fun of a manager for a rival promotion at this point?
Well, if I was booking back in '89 what would I do?
Keep him Heenan's whipping boy for a bit longer. He leaves and joins the Bushwackers but in 1990 he changes. He starts getting smarter and meaner in his promos. He orders Luke and Butch to be more brutal (turning them back into their vicious Sheepherder personas) and attack the Heenan Family.
When Andre the Giant leaves, the Brain starts talking about bringing in the perfect wrestler. He boasts and brags until April when a debuting Curt Henning arrives. Curt is in fine form, but he explains that while he did sign with a WWF manager...just not the Brain.
In walks Jamison. When the Brain orders an attack, the Bushwackers live up to their name and beat the Family. From there Jamison swears to destroy Bobby Heenan and even signs the newly turned Andre the Giant.
Jamison, Inc. would have Andre (world), Curt Henning (IC) and the Bushwackers (team) working more as tweeners. While Jamison is almost stalking Bobby Heenan and his teams, he's also going after Hulk Hogan (claiming that the faces never respected him or his wrestlers).
1990 would end with Henning and the newly arriving Rick Rude having a feud. I figure Andre would retire at some point, going with Hulk Hogan and the Big Bossman against Henning and the Bushwackers.
After that I figure Henning would leave to focus on the world title and Jamison would be kicked out when the Bushwackers and him have a Loser Leaves Town match against the newly formed Natural Disasters and Bobby Heenan. I'd have the Bushwackers come back under masks and restored to their comic personas.
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