5 times the Wilpon Family were not cheap

Johan Santana Signs the Largest Contract for a Pitcher

The next time the Wilpons broke the bank was a couple of years later when they traded for 2-time Cy Young award winner Johan Santana prior to the 2008 season. The Mets were given a couple of extra hours as part of the trade to try and agree to a contract extension with Santana, which they did when they agreed on a six-year $137.5 Million dollar deal.

The Wilpon family really broke the bank with this deal as it broke the previous franchise record with Beltran, and it also served as the largest contract for a pitcher in all of baseball at the time.

This was only the second "real" time that the Wilpons spent some money. They had made some other moves where they spent a good chunk of change but nothing close to the amount they shelled out for Santana.

This deal did not work out as well as the Beltran one, but there were some bright spots. 2009 was the first year of the extension the Wilpons gave to Santana and he ended up an All-Star while winning 13 games. 2010 saw him win 11 more games with a sub 3.00 ERA.

Unfortunately, Santana was bitten by the all too famous Mets injury bug and missed all of 2011, missed a chunk of 2012, and never pitched in the Majors again following that season. Santana was able to provide the Mets first and only no-hitter in the history of the franchise to this day.

The decision to break the bank for the Wilpons can go either way here. The Mets got two solid years following what would have been Santana's only year as a Mets and their first and only no-hitter for a rather large price.