'Bush must-win counties', 2000
These are all the counties that cast over 100,000 votes in either 1992 or 1996 (1992 being a higher-turnout election), and that either voted Republican in every election from 1968 through 1988, or voted for Bush Sr in 1992 (if both, the latter is listed, as a stronger indication of loyal Republicanism).
Unless otherwise noted, the number of votes cast is in 1996. The last time a Republican won the state without carrying the county is also listed in bold. States that voted for Bob Dole in 1996 (and therefore wouldn't under any circumstances have been considered 'swing states' in 2000) are italicised.
Arizona
Pima County (Republican 1968-1988) (264,552) (Gore) (1992)
California
San Bernardino County (Republican 1968-1988) (413,355) (Bush) (1868)
Ventura County (Republican 1968-1988) (251,194) (Bush) (1960)
Santa Barbara County (Republican 1968-1988) (150,745) (Gore) (1860)
San Joaquin County (Republican 1968-1988) (145,140) (Bush) (1896)
Monterey County (Republican 1968-1988) (108,558) (Gore) (1896)
Connecticut
Fairfield County (Bush Sr '92) (352,227) (Gore) (1880)
Florida
Palm Beach County (Republican 1948-1988) (397,354) (Gore) (1992)
Pinellas County (Republican 1968-1988) (376,272) (Gore) (1992)
Hillsborough County (Bush Sr '92) (308,271) (Bush) (1960)
Illinois
Lake County (Bush Sr '92) (203,702) (Bush) (never)
Will County (Republican 1968-1988) (147,689) (Bush) (never)
Winnebago County (Republican 1968-1988) (99,250) (112,215 in 1992) (Bush) (never)
Kentucky
Jefferson County (Republican 1968-1988) (279,913) (Gore) (never)
Louisiana
East Baton Rouge Parish (Bush Sr '92) (170,647) (Bush) (never)
Caddo Parish (Republican 1952-1964, Wallace 1968, Republican 1972-1988) (99,379) (102,678 in 1992) (Gore) (never)
Maryland
Baltimore County (Republican 1968-1988) (269,968) (Gore) (1924)
(Howard
County cast 95,508 votes in 1996 and 99,798 votes in
1992, and was Maryland's sixth-most-vote-casting county in both 1996 and 2000--realistically, it would have been a must-win for Bush in this
state as well, and it voted for Gore. [Bush Sr's margin in the state of
Maryland in 1988 came entirely from Baltimore and Howard Counties.] A Republican had last won Maryland without Howard County in 1924.)
Massachusetts
Barnstable County (Republican 1968-1988) (110,737) (Gore) (never)
Michigan
Oakland County (Bush Sr. '92) (505,642) (Gore) (1892)
Macomb County (Bush Sr. '92) (306,028) (Gore) (1956)
Ingham County (Republican 1968-1988) (116,815) (Gore) (1896)
Kalamazoo County (Republican 1968-1988) (93,135) (103,858 in 1992) (Gore) (1916)
Missouri
St Louis County (Republican 1968-1988) (462,278) (Gore) (never)
New Hampshire
Hillsborough County (Bush Sr. '92) (146,635) (Bush) (1968)
Rockingham County (Bush Sr. '92) (113,248) (Bush) (1888)
New Jersey
Bergen County (Bush Sr. '92) (362,887) (Gore) (1872)
Monmouth County (Bush Sr. '92) (248,961) (Gore) (1872)
Ocean County (Bush Sr. '92) (202,976) (Bush) (never)
Union County (Republican 1968-1988) (190,241) (Gore) (never)
Passaic County (Bush Sr. '92) (152,951) (Gore) (1948)
New Mexico
Bernalillo County (Republican 1968-1988) (182,543) (Gore) (never)
New York
Nassau County (Republican 1968-1988) (544,664) (Gore) (never [first voted in 1900])
Suffolk County (Bush Sr. '92) (505,213) (Gore) (never)
Westchester County (Republican 1968-1988) (344,863) (Gore) (1888)
Onondaga County (Republican 1968-1988) (194,939) (Gore) (never)
Staten Island (Bush Sr. '92) (128,007) (Gore) (1928)
Orange County (Bush Sr. '92) (114,538) (Bush) (1860)
Rockland County (Republican 1968-1988) (112,241) (Gore) (1888)
Dutchess County (Bush Sr. '92) (103,821) (Bush) (1872)
Oneida County (Bush Sr. '92) (94,929) (108,342 in 1992) (Bush) (1948)
North Carolina
Mecklenburg County (Bush Sr. '92) (212,845) (Bush) (1996)
Ohio
Franklin County (Bush Sr. '92) (400,515) (Gore) (1892)
Stark County (Republican 1968-1988) (158,346) (Bush) (1944)
Lake County (Bush Sr. '92) (97,736) (105,990 in 1992) (Bush) (1960)
Oregon
Washington County (Republican 1968-1988) (159,755) (Gore) (never)
Clackamas County (Republican 1968-1988) (145,146) (Bush) (never)
Marion County (Bush Sr. '92) (107,463) (Bush) (never)
Pennsylvania
Montgomery County (Republican 1968-1988) (293,961) (Gore) (1892)
Delaware County (Republican 1968-1988) (234,748) (Gore) (never)
Bucks County (Republican 1968-1988) (227,363) (Gore) (1892)
Lehigh County (Republican 1968-1988) (106,110) (Gore) (1932)
Washington
Spokane County (Republican 1968-1988) (159,232) (Bush) (never)
Wisconsin
Brown County (Bush Sr. '92) (90,837) (102,701 in 1992) (Bush) (1960)
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In 2012, analysts focussed on a group of large, historically Republican counties in swing states, which all had in common that they had voted for George W. Bush twice and against Bill Clinton at least once, had cast over 100,000 votes in 2008, and had switched to Obama in 2008. These were characterised as counties Romney had to win in order to win the 2012 election. Romney failed to win most of them, and in 2016, analysts continued to focus on them, confident that if the Democrats retained them, that would pose an insurmountable problem for the Republicans--or shocked that this was apparently not happening.
For example, in 2012, John King said of Hamilton County, Ohio, that 'If the Democrats win it, the state is gone.' Early on the night in 2016, Jonathan Karl said,
If you're looking at Florida, if you wanna look at one place on this entire map, look at Hillsborough County. That's in Tampa. No Republican has carried Florida without carrying Hillsborough County since Calvin Coolidge.
Later on, as the election began to take shape, Brit Hume said,
There are a couple of counties...Loudoun County, Virginia, being one, Hillsborough County in Florida being another, they've been bellwether counties. So far, tonight, in Loudoun County, as far as we know, Hillary Clinton is doing very well indeed, but the race in the state of Virginia is still way too close to call, correct?...And in Hillsborough County, Florida, the early results we had were that she was doing great there, and yet she's trailing in the state. So what may happen in this election is it may be that some of these counties that have been great bellwethers in the past because of their makeup may turn out not to be this time. We may have a whole new set of bellwether counties.
And Chuck Todd,
She [Hillary Clinton] did her job in Hillsborough [County, FL]...But this is not enough. She's gonna win Hillsborough and lose the state.
On the eve of the 2000 election, there was a large grouping of counties that could have been described similarly. They had cast over 100,000 votes in either 1992 and/or 1996, and had either voted to re-elect George H. W. Bush in 1992 (a clear sign of being distinctly more Republican than the nation, at least as of that election), or had voted Republican in the six straight elections of 1968-1988 (including for Ford in his narrow loss in 1976). The latter is perhaps less impressive, as it doesn't involve voting for any really badly losing Republicans. However, it was the criterion the CQ Almanac used in 1996 to define a Clinton 1992 'beachhead': 'In [1992], he won 41 counties (with at least 100,000 registered voters) that no Democratic presidential candidate had won since at least 1964.' (And most of those counties had a deeper Republican history predating the 1964 Johnson landslide.)
Now, not every county that cast over 100,000 votes and that had voted against Bill Clinton at least once, for Bush twice, and for Obama in '08 (and was in a swing state), was accounted a 'Romney must-win county'. And probably not every 'Clinton beachhead' from either '92 or '96 would have been accounted a Republican must-win county in 2000. One thing that characterised most of the 'Romney must-win counties' was that they were not only population centres, but were more particularly affluent, suburban, and well-educated. As discussed here, this may be why Brown County, Wisconsin was not generally included amongst the 'Romney must-win counties' (despite that it fit all the other characteristics of the 'Romney must-win counties', including having been the largest county in its state to have switched to Obama in 2008 and having given him a sizeable [9.1%] margin).
Likewise, not all the above counties would have been considered 'Bush must-win counties' in 2000. Some counties that it is relatively safe to say would have been considered Bush must-win counties are Oakland, MI and Montgomery and Delaware, PA, because there are actually signs here and there of their having been considered 'Bush must-win counties'. For example, on Nov. 3, 2000, Gordon Trowbridge wrote,
Republicans hope higher turnout in Oakland GOP country will reverse results of four years ago, when President Clinton was the second Democrat since 1960 to carry the county. National political pundits say Oakland is among a handful of U.S. counties that will be critical in predicting the presidential outcome.
Similarly, with regard to Pennsylvania, a number of analysts cited Montgomery and Delaware Counties (and sometimes Bucks) as critical counties in 1996 and 2000 (and even later). In a postmortem analysis of the 1996 election, Cook Rhodes wrote that
[T]o have a chance at victory, Dole needed to sweep the affluent, Republican-oriented suburbs of Philadelphia. He didn’t.
In 1992, Clinton became the first Democratic presidential candidate in more than a quarter-century to carry three of the suburban counties — Bucks, Delaware and Montgomery. And he won each of the three by a larger margin this year.
And on election night 2000, Hal Bruno alluded to Gore's surprising strength in the Philadelphia suburbs briefly after Pennsylvania was called: