The Cleveland News was a daily and Sunday American newspaper in Cleveland, Ohio. It was published from 1905 until 1960 when it was absorbed by the rival paper The Cleveland Press.
This matchbook cover appears to be from the 1950s- I could not find out what the contest was. $1000 was a nice chunk of change in the 50s!
Thanks for looking- here's the shirt info:
This classic unisex jersey short sleeve tee fits like a well-loved favorite. Soft cotton and quality print make users fall in love with it over and over again. These t-shirts have-ribbed knit collars to bolster shaping. The shoulders have taping for better fit over time. Dual side seams hold the garment's shape for longer.
.: 100% Airlume combed and ringspun cotton (fiber content may vary for different colors)
.: Light fabric (4.2 oz/yd² (142 g/m²))
.: Retail fit
.: Tear away label
.: Runs true to size