When I was four years old, my dad used to read The New York Times every day. The newspaper itself was pretty intimidating; the thing could almost engulf a four year old.  Every day, Dad would give me the sports section of The Times, and I would immediately skip to the last page where the standings were printed. I would find the team with the “Y,” go to the “GB” section, which meant games behind, and see if the Yankees had a “-1” or a “—” in their section, symbolizing where they were in the standings. That’s how I became a Yankees fan before I could read.

Once, a long time ago, the Yankees were cool. In 1996, the upstart Yanks went to the playoffs with the help of some young players such as Amertican League Rookie of the Year Derek Jeter. New York newspapers such as The Daily News and The Post might point to the birth of the “Core Four” known as Jeter, Andy Pettitte, Mariano Rivera, and Jorge Posada, but I remember the crafty veterans the most: role players such as pitcher David Cone and Dwight Gooden, who were deemed past their prime; Wade Boggs, a former Red Sox great; and Tino Martinez, claimed from Seattle.

These players gave the Yankees a rough underdog persona, as these were players that other teams did not want. These are not the home-run hitting Yankees of the Jason Giambi era; these were the pitching and small-ball Yankees that I loved to watch as a Little Leaguer. This was my team.

No player embodied the 1996-2000 Yankees more than the great Paul O’Neill. O’Neill, a favorite of Dad’s as such my own, was a ballplayer who was playing 80 years too late. He played every baseball game like he was the kid who came to the field two hours early to practice and stayed after to get some extra reps.

What might be the best part about O’Neill is that he will never be in the Hall of Fame. He never wanted the spotlight; he only wanted to improve. He famously would practice his swing while playing right field in between pitches. This was a Yankees team that cared about the team and the game.

This was the team that won 114 games in 1998, finishing 22 games ahead of that team that plays in Boston, after winning the World Series in 1996. What a year of baseball that was. Mark McGwire and Sammy Sosa were hitting home runs, the Yankees were winning, and I thought home runs were cool, unlike now with the “s” word being thrown around like a derogatory slur.

That team also had storylines to really capture the Yankee fandom. They had Derek Jeter, the hero of the squad. They had Orlando “El Duque” Hernandez, who came over to America after defecting from Cuba. They had Daryll Strawberry and Dwight Gooden, heroes of the 1986 New York Mets, who were shining in a last hurrah in the Bronx.

While my Dad loved the “played-the-game-the-right-way” O’Neill, I loved Jeter and David Wells, too. David Wells had no business being on an athletic field. He probably ate steaks during the games he wasn’t pitching. His demeanor, however, and his carefree attitude propelled “Boomer” to 18 wins. My first baseball game I ever attended was at Yankee Stadium when I witnessed David Wells’ perfect game. Other teams were just footnotes in the book of the 1998 Yankees.

And then David Wells was traded. He was traded for a Red Sox legend, and I was pretty unhappy to say the least. The Yankees were officially no longer underdogs. They had targets on their back. This is where you hear talk of the “Evil Empire.” We had officially become the heads of the playground, but now we had to start beating people up to enforce our authority.

In 2001, we met our match. I think people really forget just how good the 2001 Arizona Diamondbacks were. They had the two best pitchers of the past 20 years, and two of the top ten pitchers of all time, Curt Schilling and Randy Johnson. Luis Gonzalez hit over 50 home runs in a time when that was a big deal. They had a closer that did a funny thing with his arms when he pitched, something I often tried to emulate when I played “pitcher-and-catcher” with my friends.

And just like that, my whole life came crashing down when Mariano’s cutter blooped over Derek Jeter to score the winning run.

Losing was suddenly not an option. That’s what baseball fans do not understand about the New York Yankees. It is not an obsession with winning. It is an obsession with not losing. That’s why Yankees fans are not as excited by Aaron Boone’s Game Seven home run to beat the Red Sox as they are upset by the events of 2004 when the Sox beat the Yanks. Teams that want to win look long-term, developing a farm system, getting young players, focusing on pitching. Teams that hate losing will do anything to salvage the season.

In many ways, the 1990s Yankees could only win because they had been losing for the past 20 years; it forced them to play as a team, and it alleviated pressure on players for individual achievement. Now every free agent and every star feels like he needs to hit a homer a game or else he will be traded. This is what broke players like A-Rod, who suffered from immense pressure during his time in New York. Jason Giambi, one of the more superstitious players to ever play the game, would wear a golden thong during bad slumps in the hopes of breaking them so that he could go back to being the Jason Giambi that pitchers feared.

So this is my advice to the current non-playoff-making excuse for a team that is lucky enough to put on the pinstripes: take the pressure off yourself. You don’t need to win 114 games right now. You just need to captivate the attention of the young Yankee fans who, in an era where pro athletes aren’t role models, need you right now.

Dubbs is a member of the class of 2014.