By Dennis Gaffney

Just as DiMaggio was tough on the field, he was a hard bargainer in contract negotiations. DiMaggio usually made more money than his peers. This was undoubtedly attributed to his superior talent, but also of his ability to ask for and get good money right from the start.

Even in his first year with the Seals, DiMaggio made $225 per month when most other players were bringing home about $150. Older brother Tom helped him with the Seals’ negotiations and stepped in again when it was time to negotiate with the Yankees. The brothers turned down the Yankees’ first offer, finally agreeing on a contract worth $8,500, the highest salary the Yankees had ever paid a rookie.

With the Yankees, DiMaggio was dealing with management that was notoriously thrifty. The DiMaggio brothers, not blind to Joe’s drawing power, turned down the Yankees’ offer of $8,500 in his second year, the same amount DiMaggio earned as a rookie. DiMaggio countered with $25,000, and settled for $17,000 after an off-season of negotiations.

The next year the Yankees used the same strategy, offering the same $17,000. DiMaggio refused. This time, he asked for $40,000.

The two sides met. During their meeting, Yankee business manager Ed Barrow argued that $40,000 exceeded what they paid their steadiest of superstars, Lou Gehrig. DiMaggio, not one for quips, produced one, replying, "Then Mr. Gehrig is a badly underpaid player."

The conflict deteriorated into a stalemate. Colonel Jacob Ruppert, one of the Yankee owners, told the press that he had offered DiMaggio $25,000, "a very fair salary."

Ruppert would not budge on the offer, saying at one point, "I have nothing new on DiMaggio. I’ve forgotten all about him. Presidents go into eclipse, kings have their thrones moved from under them, business leaders go into retirement, great ballplayers pass on. . . "

DiMaggio stuck to his financial guns. (At the same time, baseball-playing DiMaggio brothers Vince and Dominic were holding out for more money from the minor league Seals.) Then, the press turned against DiMaggio. Fans, struggling through the Great Depression themselves, showed little sympathy for DiMaggio’s superstar salary demands. Then Gehrig signed for $39,000, not winning DiMaggio any sympathy points for his $40,000 demand.

Knowing he was playing hardball, DiMaggio’s hold-out continued into the first few games of the season. However, DiMaggio came to the conclusion that he was in danger of striking out altogether. He buckled, submitting to the original $25,000 offer. Showing little grace in victory, Ruppert crowed, saying, "I hope the young man has learned his lesson."

If that wasn’t a bitter enough pill to swallow, Yankee fans booed DiMaggio during his first time at the plate. It was one of the few times the Yankee Stadium crowd ever booed him, an experience DiMaggio would never forget.