Jack Ryan's universe lacks a coherent timeline, so don't bother with trying to guess when this or that happenned.
¡¡¡¡¡¡¡¡¡¡Spolier alert.!!!!!!!!!!
"Patriot games" begins with Ryan saving the prince and princess of Wales (Charles and Diana, although their names were never mentioned in the book) and their newly born first son, and ends with Jack Jr being born the following year. This means the book had to start in 1982 and end in 1983.
But, Ryan's next adventure (Red rabbit, his first mission with CIA) ends with Alí Agca's attack against Pope John Paul II, somethins that actualli happenned in 1981.
"The summ of all fears" ends between the end of Dessert Storm and the fall of the USSR, that means 1991. At the end of the book Jack Ryan leaves the CIA.
"Debt of honor" happens 3-3,5 years later, so it should be in mid-late 1994, but the story ends 11 months before next presidential ellection, according to president Durling (so this should happen at least in late 1995, early 1996).
Ryan then becomes president and stays in office for 5 years, so Rainbow six ends 1 month or so before he leaves the White House (Sidney olimpic games) ¿can "The bear and the dragon" take place in such sort time span? I seriously doubt it (I guess Tom Clancy decided to retroactively keep Jack away from a second period to save him from being in office in September 11th 2001).
Also, Ryan becomes president 10 years after the terrorist attack he suffered in "Patriot games", according to some politician. Even if it means "roughly 10 years" (most likely 12 years), Jack jr. would be 12 when Jack Sr. becomes president, 17 when he leaves, and 19-20 when Jack Sr. decides to run for the ellection again. Yet, in the book where this happens, Jack Jr. is actually 23. I guess that's what happens when you set the events of your books in a near future. Things sometimes change in a very unexpected way and the world where those events were supposed to happen no longer exists by the time they should happen.
Of course, if you forget the timeline they are great books.