I don't know where or when tomatoes were $2.49/lb. The price varies with time of year and location of the market.
I shop at Safeway here in Tucson. The prices marked in the store are not what I pay. I joined the Safeway Club to get discounts. I have to scan my Club Card or enter my phone number to get the discount. I shop on the Senior Discount day to get additional discounts. Today, tomatoes on the vine are $0.88/lb for club members. On Senior Day there is an additional discount.

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I receive Chevron gasoline discount points everytime I shop. I paid $1.02/gal on 1/24/2015. (More recently it was $1.71/gal with Safeway points.)
The points are cumulative, they add and add until used (upper limit $1/gal.)

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The stores make seniors jump through hoops to get discounts, is it stupid to jump for discounts?