Brian CashmanThe New York Yankees aren’t afraid to throw money around.

Masahiro Tanaka‘s dominance in Japan’s Nippon Professional Baseball earned the pitcher a seven-year, $155 million contract with the Yankees earlier this week. That’s a lot of dough for someone who has never thrown a pitch in Major League Baseball, but the Yankees certainly are no strangers to gambling on free agents.

The Yankees’ high-spending ways have long ticked off other fan bases, with the common complaint being that New York is trying to buy championships. The problem, however, is that spending boatloads of cash doesn’t exactly guarantee success. Sometimes, teams like the Yankees end up regretting the monster contracts they dole out. The Boston Red Sox certainly learned their lesson in recent years.

Tanaka has tremendous potential, so perhaps he’ll enjoy a great major league career and be a worthwhile investment. But there’s a chance that the Yankees’ offseason spending spree — which also includes adding Jacoby Ellsbury (seven years, $153 million), Brian McCann (five years, $85 million) and Carlos Beltran (three years, $45 million) — could backfire.

As the Yankees continue to open their checkbook this winter, let’s look back at 10 contracts that New York surely regretted not long after handing them out.

Click here for 10 awful Yankees contracts >>