Will Texas be willing to meet Montgomery's demands on contract length?
This is where this is likely to be a sticking point. I think Texas can meet Montgomery on the average annual value(AAV) on the contract. The question becomes will they be willing to go six or even seven years on the contract? Texas has not guaranteed that many years to a pitcher since Yu Darvish back in 2012. They signed Darvish out of Japan for six years and $60 million. It has become something of organizational philosophy to not give out more than five years to a pitcher. deGrom got five guaranteed seasons with an option year at the end. Lance Lynn, Mike Minor, and Kyle Gibson all signed for three years. Nathan Eovaldi signed for two years plus an option year and Andrew Heaney for one year and an option year. If you want to go way back both Chan Ho Park and Kevin Millwood signing for five years.
If reports are true then Montgomery is seeking at least six years. That would be a year longer than Texas normally likes to give out. I would think if Texas does go to six years then the sixth year will become guaranteed based on certain conditions met. That could be innings pitched in years four and five of the contract. It could be All-Star teams made or if he has won a Cy Young Award. If could be how many starts he has made. I would hope in the end that contractual length is not what keeps Texas from signing Montgomery. It absolutely could be if some other team comes in with a higher AAV and longer guaranteed contract.
Texas has to weigh how Montgomery will pitch for the life of the contract. I would think with the way he relies on command more than velocity that he will age pretty well into his mid-to-late 30's. If he can maintain the nasty curveball and sinker he throws he should be able to get batters out at a good rate for the life of the contract. Unlike some pitchers he does not have as many innings on his arm. Montgomery enters free agency with around 800 major league innings pitched. That is low compared to Aaron Nola and his 1422 innings and Blake Snell and his almost 1000 innings. I would expect despite his age of 31 that he will be a solid pitcher for at least the next few seasons and then still be good starter the rest of the contract.
Texas needs at least one more starter and Montgomery would fill that hole and give the bullpen more depth by allowing Cody Bradford to pitch out of the pen. If there is actual interest then settle the Bally Sports deal and then bring Montgomery back home. That would be a solid finish to an uneventful offseason.