The History Of WOBW
Before there was was WOBW there was a tournament and before there was Skyview Stadium their was Benny Ballpark. Like most activities that our friends partake in it will typically start with Matt Benevento. Wiffle ball was no exception to this undertaking as it started with a backyard one-on-one game between the Benevento brothers which eventually grew to the Balkun brothers and before we knew it we had a tournament scheduled for Benny Ballpark in the summer of 2016. There were even nights leading up to the tournament where the Benventos and others were playing until 2 in the morning. It was a 2v2 tournament that involved 4 teams. Winning the tournament was Alex Benevento and Brian Balkun. The tournament was such a hit it was brought back with a different field layout which included the infamous “Cookie Monster.” The “Cookie Monster” was a massive blue tarp hanging from the Benevento’s porch creating 20 foot wall in left field. Once again the tournament was a success and Matt Benevento and Maddox Underwood got to talking of how they could take this thing to new heights. Underwood and Benevento both thought a league would be awesome but the Benevento family was stern on not hosting dozens of boys every weekend in order for it to take place. So in the winter of 2017, Underwood got the approval from his parents to host the league. This made Maddox Underwood the commissioner and from that day forward the league was established, although the first league game would not be played until the summer of 2018. But that winter most of the heavy lifting was done. Underwood created a schedule, rule book, uniforms, and the overall concept of how the league would be run. Benevento and Underwood spent many winter weeknights running to Home Depot for supplies and building new things for the field. This included things like foul poles, a back stop, a strike zone, signs and more. Finally the league would draft in February. Brian Balkun, Andrew Rashad, Maddox Underwood, and Matt Benevento were all named captains of their own team and drafted the remaining 8 players in the league. They drafted in the order they’re listed in above. With that all squared away the league was ready to go and the first ever game was played in March 29th, 2018.
The league was finally underway in the early spring of 2018. The first game ever played was between Marine and Air Force, in a game Air Force would win. But looking back on it we were playing a much different game in 2018 than we were now. Our strike zone was the sand box cover for the Benevento’s 5 year old brother, and it just sat on the ground at an angle. We played with 5 balls and three strikes because our pitchers were far from experienced, and very few of us knew how to throw the pitches that we do today. Not to mention we also played in the front yard and would only play 1 game a night per team which would come out to be about 2 total games a night. In contrast, we typically will play about 6 games a night now. But some things from this era always stuck, the 2 pitcher rule is probably the most notable, as well as 2 out innings, 3 inning games, and our mercy for the inning sitting at 6 runs. But to talk about the actual game play, Air Force (2-1) and Navy (3-0) started the year hot, while Marines started (1-2) and Army (0-3). Army rattled off three straight wins while Navy did the opposite and lost 3 straight, heading into the postseason. But when it finally came down to our double elimination one-seeded Air Force mowed down everyone on their way to the finals while Army snuck past Marines in the losers bracket to earn their place in the finals. In order for Army to win, they needed to win 2 straight against Air Force and that they did. Alex Benevento was Army’s best player throughout the postseason and he was able to out duel Air Force’s Andrew Rashad in the final 2 games. This championship matchup set the pace for years to come as Air Force and Army continued to butt heads in the postseason long after this series.
In 2019, some changes were made to both the rosters and the field. The biggest changes to the field involved elevating the strike zone, and adding more lights. As for the rosters, Air Force lost star pitcher and hitter Clete Wheeler and replaced him with Navy captain Matt Benevento. In his absence Navy added Stephen Lucarelli from Air Force and free agent Garrett Ladley giving Navy the first ever roster of four. 2019 kicked off on the one year anniversary of the first ever WOBW game, March 29th, 2019. Navy’s roster of 4 was certainly not effective in their first year as they ended with a record of (2-11) by far the worst in the league. While the surprise team was definitely Marine’s with their addition of Luke Bopp, the Balkun brothers had themselves a complete lineup. Marine’s finished (8-3), as did both Army and Air Force but Marine’s won the run differential tie breaker giving them the number 1 seed in the postseason. This meant Marine’s went worst to first in the standings from 2018-2019 and is the only team to have done so to this day. But what this meant for the double elimination bracket was a first round matchup between Air Force and Army. After a dispute between Army player Reid Brown and captain Maddox Underwood earlier in the season, Brown decided to step away from the team. This left Army with a squad of two, and they came up short against Air Force in their first postseason game. Army was now on the ropes for the rest of the postseason and would have to win out. Marine’s took care of Navy in the first round but couldn’t quite topple the juggernaut that was Air Force. Air Force was once again set in the finals awaiting either Army or Marines. After a back and forth, high scoring battle it was Army that got the better of Marine’s. So once again in the finals it was a rematch between Army and Air Force. In game 1, Air Force had a chance to win the championship as they held a lead for much of the game but a come from behind victory with some late game heroics meant their would be a game 2 winner-take-all game. This game was played on a Saturday morning, and it seemed as if Air Force never woke up for this one as Army took this one handedly 13-0. After such a great game 1, game 2 was certainly disappointing. This meant Army went back to back and to this day they are the only team to do so. WOBW now had some great momentum heading into 2020 and as a league they were hungry to conquer more.
2020 can be described as the start of a new era for WOBW. For starters, it was the COVID season. We kicked off the league on March 13th, by far the earliest we ever started a season. There were record low temperatures of 45 degrees, but after our first slate of games the league came to a screeching halt. As much as, Underwood the commissioner, pushed for the league to continue, the landlords would not allow games to be played for the foreseeable future. Part of this was due to some wacky ladies of Facebook and overall fallacies regarding the virus. However, WOBW took the high road and waited until the end of May to resume the season. Over this summer WOBW was proud to report no COVID cases and no deaths, due to some of the protocols that were put in place by the WOBW board. But due to COVID, Skyview Stadium was forced to move. After being put together in the front yard, just weeks ago. Benevento the field operations manager was tasked with moving Skyview Stadium about 60 feet to the backyard. Other changes included moving the mound back several feet, and making it a 4 ball count rather than 5. In 2020 WOBW also added their first expansion team, Coast Guard who was captained by Matt Balkun who left his brother and Marine's. With 5 teams now, WOBW had an intense and long regular season since much of the rest of the world was shut down. After a 20 game regular season, Coast Guard earned the one seed totaling 15 wins, while Navy amassed just 2 wins in what became there last season. Army and Air Force were once again dead even with each other, both having a record of (13-7). Another major change was ditching the double elimination format for the playoffs. WOBW moved to a 3 game series format, with a wild card game between the 4th and 5th seed. Marine knocked out Navy in the wildcard, while Air Force and Army were set to square off in the semi finals. Finally, Air Force got their postseason revenge knocking out there rival, Army, in a 2 game sweep. Coast Guard was able to handle a hot Marine team in a very intense semi finals. We saw game 2 of this series set a WOBW attendance record as the new backyard Skyview Stadium was packed (safely) as people piled in the sandpit and patio to watch the Balkun brothers square off in an extra inning contest. This meant for the third straight year Air Force would play in the finals this time playing a new opponent in Coast Guard. One seeded Coast Guard seemed to be the consensus pick to win the series but many rooted for Air Force. Air Force in the end came through in 2 low scoring games to sweep Coast Guard and earn their name on the WOBW trophy. Due to the pandemic and long regular season some consider this to be one of the greatest seasons in WOBW history and one of the most competitive too.
After a great 2020 season and a lot still up in the air because of COVID, WOBW even experimented with a fall league after the spring/summer season. With a lot of fall high school sports being limited and up in the air, many players wanted to continue playing and so we did. The season from the jump was designed to be abbreviated, only playing a 6 game regular season. WOBW even added 2 additional teams, Space Force and Border Patrol. But with these additions Navy was disbanded as all of Navy’s team became free agents. After 6 games to everyone’s surprise Border Patrol was (5-1) and the one seed, reigning champs Air Force finished with the same record but lost the tie breaker. Those same two teams were even set to meet in the championship series after quarterfinal byes and semi-final sweeps. However this series would never be played. After the semi finals, high school football was continued in the state of Connecticut. Commissioner Underwood and 2 of 3 Air Force players were football players so much of their time and weekends were taken up by football. This made scheduling the series extremely difficult. Underwood was also on a time crunch to dismantle Skyview Stadium with winter right around the corner. For these reasons no champions were crowned during the fall season. Even if there was a championship series I would find it hard to not put an asterisk next to it due to the shortened season, and the circumstances surrounding the league. But once again the fall season provided a distraction during a very tough time period for many people and for that I am glad this season was played.
Building off of two successful 2020 campaigns, WOBW continued to grow in 2021. WOBW added new team Boy Scouts captained by Sam Ives and his squad of rookies. As expected, Boy Scouts got off to a rough (0-6) start but began to turn it around towards the end of the year, and even won a playoff series. At the start of the season WOBW was at a new high of 7 teams but they entered the postseason with just 6. Border Patrol who was created just a year ago in 2020 was forced to disband. Captain Charles Brossy and player Clete Wheeler both moved mid season leaving just Jack O’Donnell. O’Donnell was given the option to become captain and recruit 2 new players or just join a new squad. Ultimately he chose to join Air Force for the rest of the year, making it the first and only mid season move in WOBW history. Beyond that, Coast Guard came out similar to how they did in their first season grabbing the one seed with an (8-2) record. While a lot of the league floated around .500. The exceptions were Air Force and Boy Scouts who each had just 2 wins. Air Force had the biggest championship hangover WOBW has ever seen despite returning the whole squad. The team finally started to play better towards the end of the season when they added O’Donnell and even won their quarterfinal series over Space Force. The road would end there as Army once again got the better of Air Force on their way to the finals, and Coast Guard stayed strong against Boy Scouts, the team of rookies. Army went into the finals having all their weapons at their disposal as new captain Alex Benevento had this squad clicking. While Coast Guard was without their number 2 arm, Reid Brown and was largely considered underdogs in this series. Coast Guard shocked a lot of people that day and made easy work of Army. Leading the way for Coast Guard was captain Matt Balkun. Balkun was MVP and lead WOBW in many categories including ERA and was amongst the top in many hitting stats as well. But this season added many new players and was the biggest WOBW has ever been to date.
Since 2021, WOBW began to plateau in terms of growth. The league remained at 6 teams for the 2022 season but many teams were forced to add some new rookies because of a lot of limited availability. Since many players were in college now and more busy, teams regularly carried a roster of 4 or 5 people to ensure they wouldn’t be shorthanded. When the league began in 2018 all rosters had just 3 players, to compare. Many of the new rookies were rising high school seniors and juniors which helped diversify the league in terms of the age demographic. As for the season, Marine had one of the more shocking seasons finishing at the top of the league barely beating out Coast Guard and having a record of (9-1). Army experienced the complete opposite as they sported a record of (1-9). Air Force bounced back slightly as they finished (5-5) while Space Force and Boy Scouts both finished (4-6). Those same teams would meet in the quarterfinals and it was Boy Scouts that moved on. Air Force and Army also met in the quarterfinals as Air Force squeaked past a crippled Army in 3 games. Air Force had a date with Coast Guard in the semis now and after a valiant effort, Coast Guard was just too much for the Falcons as they were once again in the finals. Coast Guard was now tied with the (2018-2020) Falcons for the most finals appearances in a row with 3. On the other side of the bracket, Boy Scouts was playing the mighty Marines. Unfortunately for Marine they were missing MVP Brian Balkun. This had a clear impact on the result of the series as Boy Scouts continued rolling into the finals. The 4 seeded (4-6) Boy Scouts would now be taking on Coast Guard the reigning champs. Boy Scouts were now the only thing keeping Coast Guard from defending their title. The Scouts once again lucked out because Coast Guard was missing both Brown and Graham but Nicholas was back in Balkun’s disposal for this series despite missing much of the year. Nicholas’ return wasn’t enough for Coast Guard as Boy Scouts shocked the world with there great game plan and became the lowest seed to ever win the title and the only team with a record under .500 to win-it-all. It was an uphill battle for this team from the start and with a lot of confidence the Scouts showed that anything is possible in this great league. The 2022 season had some bumps in the road because of scheduling but ultimately the season was extremely memorable for its crazy postseason.
As great as WOBW is, it hasn't always been smooth sailing for the league. For starters, the WOBW board has always dreamed big and wanted to bring this league to the highest heights. However budget concerns have kept WOBW from making some of their aspirations a reality. For example, turfing or doming the field has been discussed but disagreements with the landlords and lack of funding has made this nearly impossible.
Furthermore we've had issues with the neighboring properties, actually just one to clarify. Due to WOBW's large collection of players and limited space on the property, cars tend to pile up beyond the driveway and the property, forcing players to occasionally park in front of other houses on the street. For many house's this isn't an issue, but for one house they have gone to great lengths to show their displeasure with this. The neighbors keyed about 4 cars one night in 2020, leading to thousands of dollars in damages and even as recently in 2022 snapped a players windshield wiper. While WOBW doesn't have concrete evidence to present to the police department or to act on this in any matter we suspect we know who the culprits are due to how the reoccurring events have stacked up. Making matters worse the police showed up to Skyview Stadium in 2022 after a noise complaint was placed at 9 p.m. on a summer evening, the same neighbors are once again suspected. The cop was probably thinking he was going to walk up on a bunch of underage kids partying and drinking, but instead found a bunch 18-20 year olds playing a child's game in a world class venue. While WOBW understands how our league may be disrupting for the people in the surrounding areas for a couple hours every couple of weeks, we are also more than willing to make accommodations to avoid interfering with others well being. Had the neighbors knocked on our door and asked people to not park in front of their house or told us to turn down the music those requests would be acted on immediately and there would be no further issues. However since these neighbors chose to get the police involved, and seriously damaged property, they have created a war with WOBW. A war in which they will not win because WOBW is a group of young, intelligent, and stubborn young men who not only try to build a community but also spread what they believe is right and what these people have done to try and stop this innocent fun, is not right.
Scheduling has also been an issue for WOBW, when 25 plus people all have to meet and play on the same night it is given that at least someone will have a conflict. Also with the springs in CT often being wet, weather also proposes an issue at times. In 2022 the first 2 weeks were played in the rain which was still fun but certainly took away from the over all experience.
Skyview Stadium has evolved in many ways over the years. However the wiffle ball addiction began in Benny Ballpark which took place just down the road at the Benevento residence. The first addition of Benny Ballpark faced the house and included a plastic green fence, two flood lights, two PVC pipe foul poles, white ribbon foul lines, a wooden pitchers mound, and a hockey net for a backstop. The field was quickly fixed to face the woods as the Benevento's elevated deck was converted into the left field wall called the "Cookie monster." Shortly after a smaller green tarp was added into right field and nicknamed the "Veggie Monster." Benny Ballpark was nowhere close to the Skyview Stadium that stands today and was much smaller due to a lack of space in the backyard, nonetheless it was still an impressive build for just a few 12 year old's.
Skyview Stadium first took shape in the year 2018 when WOWBs first season occurred. The field saw some major improvements from Benny Ballpark. Four flood lights were added down the left and right field lines, as well as additional two smaller flood lights in center. The Underwood's rockwall would serve as the fence in left field, and the green plastic fence continued to be used as the center field and right field fence. Some additional signs, flags, as well as a real backstop and improved mound were added to the field as well. Some of the most iconic signs include the McDonald's sign, the Subway sign, and the Bud Light sign. White ribbons were still used as the foul lines as well as the PVC pipes continuing to be the foul poles. The first ever Skyview Stadium was a beautiful thing, however it would continue to improve as time went on.
The 2019 stadium saw a few key changes that would help the league function smoother. The strike zone was changed from the cover of the Benevento's sandbox, to an elevated PVC pipe strike zone with a plastic piece in the middle. Late in the 2019 season Commissioner Maddox threw a lacrosse ball at the plastic strike zone putting a hole in the very middle. Although members of the league were not happy at first, this incident turned out to be a blessing in disguise. The zone would then be replaced with galvanized sheet metal that is still seen in the strike zone today. The sheet metal gives a loud ring each time the ball hits making it clear when a strike is thrown. Another key change to the 2019 field was getting rid of the ribbon foul lines and getting the okay from the Underwood family to spray paint lines onto the field. This eliminated the tripping hazard that the ribbon created and made the field look more professional. Although there weren't many large changes to the field in the 2019 season, the changes that were made proved to be important and drastically improved WOBW today.
With COVID-19 being an issue in the 2020 season and the New Canaan Mom's Facebook page putting WOBW on blast for playing wiffle ball during the pandemic, the Wiff or be Wiffed board made the executive decision to move the field to the backyard. This was one of the greatest things that ever could have happened to WOBW. The backyard patio was a perfect seating arrangement for those who weren't playing. The field also no longer had to deal with the thorn bush that was on the right side of the infield. After setting up the field in the back it quickly became clear to WOBW that this would serve as the leagues permanent new home. In left field the patio rock wall would serve as the fence and then the original green plastic fence would stretch all the way through center. In right field there was a short porch due to the Underwood's sand pit and therefore an elevated fence was needed. In the 2020 season WOBW used a thin deer netting fence that was difficult to see from a far. This made it interesting when the ball was hit this way as you couldn't tell if it was going out or staying in until the ball reached the fence. Overall the switch to the backyard was clearly a good move for WOBW.
The 2020 fall league saw massive changes in terms of the field. Spirits were high after a fantastic 202o summer season and WOBW wanted to spruce up the field. Although this was the goal, the 2020 fall field was arguably the biggest flop in WOBW history. Members of the league invested in around 25 sheets of tempered hardboard that would be used as the center field fence (pictured to the right.) The team then painted all the boards blue and added signs along the fence in white. Although the field looked better than ever in the first few weeks, after around 2 weeks in the elements that fence began to fold and fall over constantly. This was extremely discouraging as lots of time and money were put into the project. The fence would only serve the fall season and proved to be a compete failure. In the fall 2020 season WOBW also stacked the original green fence to create a larger wall in right field. Although there is no doubt that this was the best Skyview Stadium has ever looked, It came with a price that was certainly not worth it.
After the 2020 fall season field fail, it was time for WOBW to go back to what they knew would work. The left field fence was changed to a new orange plastic one as the green fence has finally run its course. The right field wall was replaces with tiki which was another element that was difficult to deal with. This fence was by far the tallest right field wall that WOBW had ever seen and the sheer weight of the beast made it so that it would fall over often. The fence made it through the entirety of the season however it was difficult to keep up with the fence as it had to be fixed every week. There were also a few windy nights where the fence fell during play. Overall the 2021 field was another good looking one. Some notable changes were the spray painted WOBW that is shown to the right and well as additional lighting.
In the 2022 season WOBW decided to go simple and it paid off. The league decided to use what was left of the original green fence in left-center and then the orange fence in right field. This year the league would play through the sandpit and it caused for many more balls to be in play. With the flags along the entirety of the fence this field proved to be one of WOBW's sharpest. This field was also one of the easiest to maintain. WOBW has seen many different forms over the years and some certainly worked better then others. I think everyone in the league can agree that they wouldn't have the evolution of Skyview Stadium go any other way. It is always a joy each and every year making the trip to Home depot and partaking in build day.
2022
Wiff or be Wiffed has been around for 6 years now and has had a tremendous history. The WOBW community is beyond excited to continue the glorious heratige that is Wiff or be Wiffed.