Possible Clues:

• Two-time loser to Dwight
• Loser to Dwight
• Runner-up to Ike
• Two-time loser to Ike
• Politico Stevenson
• Dwight's opponent
• Dwight's two-time opponent
• Name in 50's politics
• Ike's two-time opponent
• First name in 1950s politics