Cursed Senate seats

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Florida, Class 3

Cursed Since 1968

Edward J. Gurney (1967-1974) - defeated for reelection
Richard Stone (1975-1980) - defeated for renomination
Paula Hawkins (1981-1987) - defeated for reelection

After three terms of Bob Graham, it resumed

Mel Martinez (2005-2009) - resigned
George LeMieux (2009-2011) - an appointed placeholder
Marco Rubio (2011-) - forgo reelection in order to purse a failed presidential bid


Illinois, Class 3

Alan J. Dixon (1981-1993) - defeated for renomination
Carol Moseley Braun (1993-1999) - defeated for reelection
Peter Fitzgerald (1999-2005) - did not seek reelection
Barack Obama (2005-2008) - getting elected President is not very cursable, but he still served less than 4 years
Roland Burris (2009-2010) - appointed under extremely controversial circumstances, forgo a hopeless election bid
Mark Kirk (2010-) - suffered a stroke during his term, likely to lose reelection


North Carolina, Class 3

Robert Burren Morgan (1975-1981) - defeated for reelection
John Porter East (1981-1986) - announced he won't seek reelection after being diagnosed with a low thyroid, then committed suicide
Jim Broyhill (1986) - appointed and defeated
Terry Sanford (1986-1993) - lost reelection in an upset
Lauch Faircloth (1993-1999) - defeated for reelection
John Edwards (1999-2005) - forgo reelection in order to purse a failed presidential bid
Richard Burr (2005-) - appears to broke the cycle, winning reelection in 2004 and being favored to do so again this year

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Tennessee was somewhat "cursed" for Solid South standards, as only McKeller served more than 3 terms.

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Kentucky, Class 2

William A. Stanfill (1945-1946) - a placeholder
John Sherman Cooper (1946-1949) - defeated for reelection
Virgin Chapman (1959-1951) - killed in an automobile accident
Thomas R. Underwood (1951-1952) - appointed, then defeated
John Sherman Cooper (1952-1955) - defeated for reelection, again
Alben W. Barkley (1955-1956) - dies in office
Robert Humphreys (1956) - a placeholder
John Sherman Cooper (1956-1973) - finally, he managed to keep this hot seat until retirement
Walter Dee Huddleston (1973-1985) - defeated in an extremely close race (49.9%-to-49.5%) due to Reagan reelection coattails
Mitch McConnell (1985) - managed to broke the curse, but had some close calls

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Not a Senate, but Illinois' 2nd district seems to be rather unfortunate in recent years

Gus Savage (D), 1981-1993 - defeated for renomination, tenure dodged with frequent close primary races and racist remarks
Mel Reynolds (D), 1993-1995 - resigned after a conviction for statutory rape, then went to federal prison on 16 unrelated counts of bank fraud
Jesse Jackson, Jr. (D), 1995-2012 - resigned and was promptly convicted of charges of fraud, conspiracy, making false statements, mail fraud, wire fraud, and criminal forfeiture (wow, that's a yuge list). Served time in federal prison before being released to a halfway house


And, of course, who could have forget about Illinois Governorship?

William Stratton (R), 1953-1961 - tried and acquitted on charges of tax evasion in 1965
Otto Kerner (D), 1961-1968 - was sentenced to three years in federal prison in Chicago and fined $50,000 after his Governorship
Samuel H. Shapiro (D), 1968-1969 - became Governor after Kerner's resignation, defeated in a bid for a full term
Richard B. Ogilvie (R), 1969-1973 - defeated for reelection
Dan Walker (D), 1973-1977 - defeated for renomination, later served eighteen months of his seven-year sentence
James Thompson (R), 1977-1991 - nothing
Jim Edgar (R), 1991-1999 - nothing
George Ryan (R), 1999-2003 - did not seek reelection, later convicted of federal corruption charges and spent more than five years in federal prison
Rod Blagojevich (D), 2003-2009 - OK, we all remember what happened
Pat Quinn (D), 2009-2015 - became Governor after Blago's impeachment, narrowly elected in 2010 and defeated for reelection in 2014

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Mark Kirk (2010-) - suffered a stroke during his term, likely to lose reelection

I wouldn't say he's likely to lose.  I'd say his shots are 50-50.

Fair point, but we can agree he's by no means secure.

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And if we're talking about different offices too, the New York Lt. Governorship was FUBAR for 2008-2010.

https://en.wikipedia.org/wiki/List_of_Governors_of_New_York#List_of_governors

Those people weren't Lieutenant Governors, but Presidents of the Senate who became first in the line of successions. "Acting Lieutenant Governor" was a title of courtesy.