By TRACIE CONESTOCKTON, Calif. (AP) â¿¿ By outward appearances, Stockton, a city of nearly 300,000 on the Sacramento-San Joaquin River Delta, seemed in the mid-2000s to be emerging from decades of struggle. Next to its gleaming downtown waterfront â¿¿ a window to the West's largest fresh-water estuary â¿¿ a beautiful new $46 million glass hockey arena rose in 2005. That same year, the Oakland A's single-A affiliate Ports began play in a new taxpayer-financed stadium, amenities sought by elected officials catering to a wave of new residents fleeing Bay Area congestion and home prices. High salaries and lucrative benefits were supposed to attract and retain the brightest city workforce to improve the quality of life for its residents. "We spent like the good times would go on forever," said Stockton spokeswoman Connie Cochrane. But then the recession hit, and the good times went bust. On Monday, the state's 13th-largest city begins federal court proceedings that could end with it becoming the most populous in the nation to successfully enter Chapter 9 bankruptcy, a move opposed by those who lent the money to keep it flush. On its journey to this point, the Central Valley city has become emblematic of both government excess and the financial calamity that resulted when the nation's housing bubble burst. Its salaries, benefits and borrowing were based on anticipated long-term developer fees and increasing property tax revenue. But those were lost in a flurry of foreclosures. After the city's population grew by nearly 20 percent between 2000 and 2005 and real estate tripled in value, home prices plummeted 40 percent the following year before bottoming out at 70 percent. Within two years, Stockton had accumulated nearly $1 billion in debt on civic improvements, money owed to pay pension contributions and the most generous health care benefit in the state â¿¿ coverage for life for all retirees plus a dependent no matter how long they had worked for the city.