It can imply skilled negotiating that's impressive and resourceful, often viewed positively. He managed to wheel and deal his way to a great deal on the property.
Pro Tip 2/3
Colloquial Use
It's informal and best used in casual conversations or in business slang. To succeed in the market, you've got to know how to wheel and deal.
Pro Tip 3/3
Business Acumen
Often associated with shrewd business practices or savvy investment strategies. She had to wheel and deal to get ahead in the competitive tech industry.