5 times the Wilpon Family were not cheap

If you ask any New York Mets fan or even baseball fan for that matter, they should know that the Wilpon family always had the tendency to be on the cheaper side.

The Wilpon family originally became part owners of the Mets back in 1980 when they bought a 5% stake of the team. Fast forward to the end of 1986 and the Wilpons would become 50% shareholders. Now fast forward even more to August of 2002 when the Wilpons become the sole owners of the team in orange and blue.

Although the Mets did win and spend money with the Wilpon family as owners throughout their ownership tenure, I am going to focus on the time period where they were strictly the sole owners of the team as times when they were not cheap. While they did have a few years where they were 50% owners, they were not majority owners and as a result, not all financial decisions were made with 100% of their control.

Despite most people's beliefs, the Wilpon family did have some moments where they were not cheap.

Even though the Wilpons have had the reputation of being cheap and not really making an attempt at putting a winning team on the field, there have been a handful of times where they did break out the checkbook in an attempt to put a winner on the field.

Now even though the Wilpons did never win when they were majority owners of the team, their handful of moves when they decided to spend was not necessarily the problem, as the times they did break the bank turned out to be pretty decent.

As previously stated we are strictly looking at money spent once the Wilpon family were majority owners, so post 2002. With that being said, let's look at five times the Wilpon family were not cheap.

Carlos Beltran Signs the Largest Mets Deal in Team History

Following his 2004 season where he put up career-high numbers in multiple different offensive categories, was awarded to his first career All-Star team, finished 12th in MVP voting, and had one of the most insane postseason stretches in Major League Baseball history, Carlos Beltran cashed in on a seven-year, $119 Million dollar contract with the Amazins.

At the time of the contract, this was the biggest deal in Mets history, and rightfully so. This was the first time the Wilpons spent some real money since they became the majority owners a few years prior.

Even though the Mets did not win following the monster contract they gave Beltran, it did work out pretty well. He was a five-time All-Star, three-time Gold Glove winner, two-time Silver Slugger winner, and had a fourth place finish in MVP voting one season.

Everyone loves to point out how he struck out in game seven of the NLCS in 2006 to end the Mets season, but you cannot have one single moment shadow over the rest of his accomplishments in New York. The Wilpons spent a large amount of money on Beltran and it worked out well as a whole.

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.

Wright signs largest contract in New York Mets history

Following the Bernie Madoff scandal, the Wilpons really cut back on their willingness to spend as they lost a significant amount of money. After a couple of years of some poor Mets teams, the Wilpons opened up their checkbooks once again in December of 2012 and made one of the biggest investments in a player in the history of the franchise when they gave David Wright a seven-year $122 million extension.

When you include the 1-year $16 million Wright was already owned, it made his total contract worth $500,000 more than Santanas from years prior. This was the largest contract in the history of the Mets at this time.

Not only was this a huge deal for the Mets and their fans at the time because of the lack of spending in recent years, but they also locked up the face of the franchise for the foreseeable future and did not have to worry about potentially losing him in free agency.

With Wright still having a year left on his contract at the time, his extension did not technically kick in until 2014. Unfortunately for the Mets and Wright, he was bitten by the injury bug like many other Mets and was never the David Wright everyone expected him to be.

In terms of getting what you paid for and the money being "worth it", the saving grace for the Wilpons here was the insurance plan they took out on Wright's contract. Extending him and spending the money was no doubt worth it at the time. He had only missed a significant amount of games once in his career at that point and he was the face of the franchise.

deGrom signs 2nd biggest contract in Mets history

Move into 2019 and we have the last time the Wilpon family spent some money. Just before the start of the season, the Mets reached a contract extension with the reigning Cy Young Award winner in Jacob deGrom. deGrom was still under contract through 2020 but, the Mets decided to extend their ace right after he won the Cy Young award.

At the end of March 2019, deGrom signed a 5-year extension worth 137.5 million. It can also grow up to $170 million if the Mets pick up a team option for a sixth year. deGrom's former agent and then Mets general manager Brodie Van Wagenen, locked up the Cy Young winner just a few months after taking over. While he was deGrom's agent he made a comment about how the Mets should either extend deGrom or trade him, so when he became the general manager he took the matters into his own hands and extended him.

At the time of the extension, deGrom had the second-biggest contract in Mets history. It was the same amount of money as Santana and just $500k short of Wright's extension.

That 2019 season that started up right after the Mets extended their ace was deGroms first year of the extension at it took over his contract at the time. The Wilpon's decision to spend on deGrom paid off immediately as he went on to win the Cy Young award for the second straight year.

Although deGrom was unable to win his third in a row in the shortened 2020 season, he still ended up finishing third in Cy Young voting. 2021 he was on pace for one of the greatest pitching seasons in the history of the game before going down with an injury. Despite only starting 15 games, he still posted a 1.08 ERA in 92 innings and finished 9th in Cy Young voting while being named an All-Star.

It is hard to fully judge if the Wilpons decision to spend was good or not as the full contract has not concluded yet, but so far it appears to be money well spent. deGrom won the Cy Young his first year, finished third the next, and was well on his way to another one before getting hurt in 2021. So long he stays healthy and can even be 80% of the pitcher he is when fully healthy, it should be the best money spent for the Wilpons in their tenure as owners.

The Wilpon family had always been hesitant to break the bank and when they did, it did not always work out the best for them. Spending on deGrom and Beltran worked out well for the most part, but spending on Santana, Wright, and Cespedes was not as good. It is not like the Wilpons spent money on players that just didn't perform, they all got hurt and could not physically play.