Did Paul actually suffer the way Jesus said he would?
Yes. Acts 9 records the Lord telling Ananias that He would show Saul how great things he must suffer for His name's sake. The Corinthian letters document that suffering: Paul was beaten, scourged, cold, naked, often sick, and living in fear for his life.
Les explains that Acts 9 is the key. When the Lord Jesus spoke to Ananias, He said Saul would bear His name before the Gentiles, kings, and the children of Israel. Then in verse 16 Christ said, “For I will show him how great things he must suffer for my name’s sake.” Les asks, “And did he? Oh did he!” He points to the Corinthian letters, where Paul was beaten, scourged, cold, naked, many times sick, and living in fear for his life—all because of what the Lord Jesus had promised him. Les then ties this back to Galatians 1, explaining that this is what Paul is making reference to: the Lord was going to reveal Himself in this man, the apostle Saul of Tarsus, now known as Paul.
For I will shew him how great things he must suffer for my name’s sake.
Are they ministers of Christ? (I speak as a fool) I am more; in labours more abundant, in stripes above measure, in prisons more frequent, in deaths oft.
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In what context would Paul suffer great things for Christ's name?
The great things Paul must suffer for God's name would be suffered in the ministry.