In a 2009 bowl game against North Carolina, Pitt needed a few yards for a first down and had to decide whether to go for it or kick a field goal. Pitt’s coach at the time, Dave Wannstedt, still remembers the response of offensive lineman Jason Pinkston, a Baldwin Class of 2006 alum.
“He said, ‘Let’s run that thing,’ ” Wannstedt said. “And I said, ‘If we jump offside, we’re dead. We’re going to lose the game.’ And he says, ‘Hey, Coach, trust us. We will execute it.’ And we went in, executed the play, got the first down, and went on to win the game.”
That was just one moment in Pinkston’s football career, which started at Baldwin and eventually led to several seasons playing for the Cleveland Browns in the NFL. But it was a key one, Wannstedt said.
“I bring that story up because it’s one that’s not about knocking somebody down, which he did a lot of times as an offensive lineman,” said Wannstedt, who is also a Baldwin alum. “That’s more about his football intelligence and understanding of what we had to do.”
Looking back, Pinkston recognizes the importance of that game.
“My best Pitt game was probably our bowl game against North Carolina. We beat them to secure our 10th win of the season. Pitt hadn’t achieved that in years,” Pinkston said.
But his football journey began much earlier, kick-started in the weight room at Baldwin High School, where he put in the work between his sophomore and junior seasons.
Pinkston got in the weight room that summer and put on muscle, allowing him to make the switch from tight end, which he had played as an underclassman, to offensive line. He worked with trainers to help him become the best athlete he could be.
Co-Principal John Saras was a middle school football coach at the time.
“Something clicked. As a freshman or sophomore, he was just kind of feeling things out. But from that sophomore to junior year, something clicked – that dedication in the offseason,” Saras said.
As Pinkston looks back on his playing career and his life, he knows the important role Baldwin played.
“Baldwin is where I really got my start. It was the beginning of my journey,” Pinkston said.
At one time in his youth, Pinkston had wanted to become a firefighter. But soon football became the goal.
“I still have that love for firefighters and what they do,” Pinkston said. “But my number one dream was to play in the NFL, to run out of a tunnel on a Sunday.”
Like many young athletes, his parents played a role in developing an interest in his sport.
“I grew up watching football with my parents. I was a big Reggie White fan at that time, and I was just in love with the Green Bay Packers,” Pinkston said.
At Baldwin, Pinkston got some minutes on the field as a freshman, and he started as a sophomore. He soon became a star for the Highlanders.
“He was a competitor. When he got on the field, he wanted to win more than anything,” math teacher Thomas Simcho said.
Pinkston credits much of his success to his coaches at Baldwin.
“Our coaching staff, Mike Silianoff and Tim Robbins, did a great job keeping me focused and present in the moment. I didn’t stress about college coaches visiting our games – I stayed excited and focused on performing at the highest level I could,” Pinkston said.
Pinkston showed heart every time he stepped onto the field, Saras said, noting “his dedication, persistence, passion for football, and his passion to get better.”
At that time, the offensive line was a strength for Baldwin.
“There was a close-knit bond amongst those guys that played line, and they were a cohesive unit,” Saras said.
Pinkston especially remembers a game during his sophomore year.
“We were playing Penn Hills at their home field, and they were ranked No. 1 in the WPIAL. The atmosphere was electric, and the pressure was huge,” Pinkston said. “But our preparation and belief in each other paid off – we pulled off a 21-14 victory. That win wasn’t just about the score. It showed me what our team could accomplish when we stayed disciplined, trusted the process, and played for each other.”
In the offseason, Pinkston played other sports, like basketball, to stay in shape and keep ready for the football season. Simcho coached Pinkston during his freshman year basketball season.
“Certain people have certain physical gifts that you can’t teach, and Jason was blessed with a lot of physical gifts, such as size and strength,” Simcho said.
During his time at Baldwin, Pinkston felt the pressure of being a student-athlete. He learned time management skills that would help him later in life.
“The biggest challenge for me was balancing schoolwork with playing football,” Pinkston said. “Learning how to plan my days, get to class on time, and manage life on my own without your parents around to wake me up or make sure I’m studying, took a lot of growing up and responsibility.”
Pinkston also worked in the classroom with Simcho during tutoring sessions.
“We worked together a lot, as far as the academic piece,” Simcho said. “He was smart, and he was a very cordial kid, very easy to get along with.”
After graduating from Baldwin, Pinkston had offers from Ohio State, Penn State, Louisiana State, Georgia, and USC. But he took his talents to the University of Pittsburgh.
“My entire family grew up as Pitt fans. My aunt lived right next to the old stadium when it was in Oakland, and I have memories of going to the games with my family,” Pinkston said.
Getting Pinkston at Pitt had been a priority for Wannstedt.
“Recruiting in Western Pennsylvania was a priority, and on top of that, when you see somebody from your high school who’s getting recognition, that was a big priority,” Wannstedt said. “You always have a little bit more love pulling for guys from the neighborhood, and that’s kind of how I looked at Jason.”
While at Pitt, Pinkston learned many skills that would eventually be translated into an NFL career. Wannstedt and offensive line coach Tony Wise had coached under Jimmy Johnson for the Dallas Cowboys, and Pinkston credits them for many of his achievements.
“Playing that pro-style offense, with pro-style terms, helped me be successful and translate over to the NFL,” Pinkston said.
Wannstedt said Wise recognized Pinkston’s talents early on.
“I remember Tony Wise coming to me and saying, ‘This guy’s athletic. He’s a tough guy. He will be a really good offensive lineman,’ Wannstedt said. “So we just left Jason there, and as he matured, he got smarter and tougher, and his game just got better and better.”
Pinkston redshirted his first year, and the following year, he started three games before suffering a shoulder injury against Michigan State. But in his junior year, he was named first-team All-Big East and second-team All-American.
Another key college memory for Pinkston was the famous “Backyard Brawl” rivalry game with West Virginia in 2007.
“As a team, our most memorable win was knocking off West Virginia 13-9. That victory kept WVU from playing in the national championship and is considered one of the biggest in program history,” Pinkston said.
In the 2011 NFL draft, Pinkston was drafted by the Cleveland Browns in the fifth round.
When the Browns’ offensive guard starter ahead of him got injured, Pinkston was thrown into the fire his rookie season. He played well in the position, and his level of play earned him a spot on the line, with Pinkston ending up starting all 16 games in the 2011 NFL season.
“I looked forward to playing the Steelers. They were my hometown team,” Pinkston said.
Wannstedt followed Pinkston’s career in Cleveland.
“He became kind of a dominating offensive lineman, and he understood things,” Wannstedt said. “His football intelligence would be the word.” Wannstedt said.
After playing for Cleveland for four years, Pinkston was forced to retire for medical reasons. Previously, he had suffered a blood clot in his lung, which led to him being hospitalized. After he suffered another blood clot during a game and had to retire, he was heartbroken.
“I had worked my whole life to live out my dream, and it felt cut short after only four years,” Pinkston said. “Yet I was grateful just to be alive. Since 2014 I’ve fully healed from blood clots and haven’t had any issues.”
After his football career was cut short, Pinkston founded and became CEO of South Pointe Construction Services in 2016. He also served as an offensive and defensive line coach for the South Hills Chargers. Later, Pinkston spent time assistant coaching for the Seton LaSalle High School Rebels, and he is currently the offensive line coach for the Central Catholic High School Vikings.
He also does public speaking at high schools and other venues, covering his career and life experiences, as well as acting as a mentor to students around the Pittsburgh area. Earlier in the school year, Pinkston visited Baldwin High School for a presentation geared toward students in a pop-culture class.
“I think the presentation gave us motivation to help us learn what we want to do in the future,” senior Isabella Niles said.
The presentation was also valuable for Baldwin football players, as Pinkston talked about his progression playing football from Baldwin to Pitt and then to the NFL.
“The presentation showed me that someone else was successful in this career, and his journey began similarly to mine, which gives me hope that either my brother or I will have a career in this,” senior Michael Coates said.
Throughout his life, Pinkston has worked for his future. Sometimes, though, he takes a minute to reflect on the past and what got him to where he is now.
“There are really great teachers at Baldwin High School who counted on me to do the right thing and show other kids the right way to do things,” Pinkston said.
Wannstedt said he is impressed by the success Pinkston has had in life.
“The guy’s got something to him,” Wannstedt said. “He’s a businessman, and he’s got a great wife and family. You just love seeing guys, not just recruited to Pitt, but from your hometown, to have that type of success.”
Saras agrees, saying Pinkston remains a person of great character.
“Even to this day, he is such a people person. In my opinion, he just likes life,” Saras said.
Looking back, Pinkston is happy with his NFL career.
“Obviously, I came short of the Super Bowl,” he said. “But to live out my dream and to be able to share that with my family and my kids – it’s very surreal.”
