Ryan Dempster hopes Cubs and Kris Bryant stick together

Chicago Cubs (Photo by Dylan Buell/Getty Images)
Chicago Cubs (Photo by Dylan Buell/Getty Images) /

Former Chicago Cubs pitcher Ryan Dempster, now “Off the Mound” host on the Marquee Sports Network, hopes Kris Bryant remains with the Cubs.

The best start to a career with the Chicago Cubs belongs to Kris Bryant. And it isn’t close. Bryant won every award possible, culminating with a drought-ending World Series championship in his first two years in Cubs pinstripes.

But did Bryant’s incredible performance on the field come with the cost of raised expectations that he has never been able to duplicate?

“I think he set the bar crazy high,” Ryan Dempster told Da Windy City podcast. “Golden spikes winner, minor league player of the year, rookie of the year, MVP, World Series champion, doing it all and then he hits .280 with 30 or something and we are like ‘what happened to Kris Bryant’? Thats a lot to carry around and the expectations of that.”

Bryant hit those numbers in 2019, but the discussion was whether Bryant was a clutch player. Any prior playoff successes were long forgotten, and now Bryant’s injury-riddled nightmare 2020 season where nothing went right. He finished with an abysmal .204 batting average, only four home runs.

Bryant enters his final contract year with rumors swirling that he has played his last game in a Cubs uniform, even if the Cubs are unable to get fair value in a trade. Bryant’s bounce back contract year will, in all likelihood, benefit another franchise.

Bryant has said numerous times he wants to stay in Chicago. The Cubs have made at least one long term offer to Bryant that his agents deemed too low at the time. Dempster believes there is some common ground between the two parties.

“I’m sure they (Cubs) do and I’m sure he (Bryant) wants to (sign a longterm deal), but we know there are two sides to everything, right. There’s agents and there’s players trying to get the best contract they can get, and there’s teams trying to manage payrolls all of those things,” Dempster said.

Some have speculated that Bryant would be happy elsewhere. The expectations and the bright lights playing in Chicago are “not the best fit” for the easy-going Bryant. Dempster believes all the early success may have taken a toll on Bryant.

“I’m not saying he is Michael Jordan in this town, but especially after the 2016 season you could argue he was as popular as Michael was in those championships,” Dempster said. “Guy can’t go to the grocery store without 100 people asking for a picture and that’s not everybody’s cup of tea — that’s a hard thing to try and take in all the time.”

True, Bryant is not Jordan. But, he was Cub-Jordan for a while and remains extremely popular. At 6-foot-5 he can’t exactly blend in like most baseball players. The Cubs’ parade in 2015 drew an estimated five million people to Grant Park. Life in Chicago as a Cub had changed dramatically.

Things are back to “normal” now. The Cubs have very little expectations. The baseball buzz in Chicago is tilted towards the up and coming White Sox, not the getting old and stale Cubs. It might take Bryant having another MVP year to get Cubs fans excited, which again seems more likely to happen elsewhere.

No matter what happens going forward Dempster will always appreciate and respect Bryant for how he carried himself in a Cub uniform.

“I just think he’s had an incredible amount of expectations on him and he has handled it all extremely well,” Dempster said. “He has been a pro through it all, a team-win first guy always. One of my favorite people around. I hope he is a Chicago Cub the rest of his career. If not, I hope he gets everything he deserves because he’s earned every bit of it.”

Change is coming to Wrigley Field. Theo Epstein will reportedly depart after next season. Trades are coming before that. Will Bryant be the first to go?