The race for supervisor in the South County may not be the most expensive of all.

Gary Simpson, the former Napa County sheriff running for supervisor in District 5 has raised and spent about three times as much as his rival, Keith Caldwell, the retired American Canyon fire chief.

The District 5 supervisor represents American Canyon, unincorporated areas east of Napa and the southern tip of the city of Napa.

According to campaign finance statements on file at the Napa County Elections Department, Simpson has raised about $135,000 since the summer of 2007, including $113,000 this year.

Caldwell, for his part, has raised about $40,000, including $12,000 since July 2008. Caldwell only raised $200 last fall, campaign finance records show.

Simpson has spent close to $90,000 so far, including about $77,000 since Jan. 1. Since July 1, he spent about $28,000 on campaign literature, marketing and campaign events. As of Sept. 30, he had $43,000 on hand.

Caldwell has spent about $30,000 on his campaign, including $5,000 since this summer. As of Sept. 30, he had about $10,000 on hand.

Simpson drew donations of $500 or more, while Caldwell received about two-dozen donations less than $500.

Both candidates received money from Upvalley wineries.

Caldwell won the preliminary race in June thanks to American Canyon while Simpson carried the vote north of the Soscol ridge.

Simpson retired in December 2006 after running the Napa County Sheriff’s Department for two decades, while Caldwell served 17 years as fire chief until his retirement in 2007.

Whoever wins the election will replace retiring Supervisor Harold Moskowite.

Listed are contributions of $500 or more between July 1 and Sept. 30:

• Gary Simpson:

$500: Sawyer Vineyards of Jacksonville, Fla.; Robert MacDonnell of San Mateo; Silverado Partners of Napa;  Mel Gelow of Napa; Tulocay Partners of Vacaville; Cameron Baker of Belvedere; William Simpson of Napa; DJ Smith of Napa; Stan Teaderman of Napa; Bruce and Rosemary Cakebread of St. Helena; Louis Daugherty of Napa; Geraldine Drew of Napa; Joseph Phelps Vineyards of St. Helena; Gene Waken of Napa; 600 Tower Road Operations; Laird Family Vineyards; Sheet Metal Workers Local Union 104 of San Ramon; Jim and Cindy York;

$550: Harry Price of Napa;

$552: Layer Cake of Rutherford

$600: Dolores and Jack Cakebread of Rutherford;

$945: Stanly Ranch Vineyards of Napa;

$1,000: Castello di Amorosa; Garrett and Beverly Brown of Napa; Nathan Topol of Reno, Nev.; Vera Trinchero Torres of St. Helena; Carmen Policy of Yountville; California Citizens for Excellence in Government of Sacramento; The Meritage Resort; Patrick Croston of Napa; Gretchen Maglich of Wayzata, Minn.; Michael Maglich of Wayzata, Minn.;

$1,010: Icon Estate of St. Helena

$1,198: William Bacigalupi of Napa

$1,500: Andrews and Thornley Construction of Napa; Jess Jackson of Santa Rosa;

$2,500: Paul Loomis of Napa; J. Michael Murphy of Napa; Green Tree Properties of Napa;

$5,000: One True Vine of St. Helena;

• Keith Caldwell:

$500: Joseph Phelps Vineyard LLC of St. Helena; Robert Torres of St. Helena; G. L. Mezzetta Inc. of American Canyon

$1,000: Friends of Pat Wiggins of Santa Rosa; Volker Eisele of St. Helena

$2,500: Barbara Winiarski of Napa